Waiting for inspiration

Like a lot of people I talk to these days, I’ve been feeling rudderless. That is not to say I’m miserable - I’m not. In fact, I might be happier than I’ve ever been. I am doing good work with people I love working with. But I also have this gnawing feeling I’m running out of time to do something more meaningful with the waning years I have left. I know there is something more, something I can offer the world no one else can. Some days I think I have it, only to have it slip away. It’s like I’m in a fog, the answer lurking just beyond my grasp. And it’s not for a lack of trying. I talk to people every day about it, because we’re all going through it together. I write about it. I talk to guests on the podcast about it. And it feels like the harder I try, the more elusive the answer becomes.

So when I got the chance to go back-country canoeing for a week, it seemed like the perfect opportunity to leave all this congested restlessness behind. I know the answers we’re looking for never show up when we’re trying so hard. So this seemed like just what the self-help gurus ordered. If I could distance myself from the noise, something would come to me. Surely, it had to. In the quiet, there would be nothing left but the obvious answer that had been waiting there all this time. It was a brilliant plan.

But as my time in the woods drew to a close, it became clear no lightning bolt was coming. I spent five days being present, doing my best to clear my mind, and simply marvelling at the beauty of the fluffy clouds, sparking waters and the rock that had been there long before people paddled by trying to forget their troubles. I started thinking it was all a big waste of time. I needed answers! Where were my answers?

What would the rocks say?

It’s amazing what starts to appear when you stare at something long enough. Like how animals and faces start to emerge in the clouds. They’re there, then they’re gone, changing into something else or nothing at all. I started seeing faces in that billion years of rock. Elephants. Alligators. Kings and queens. And a couple of paddle strokes later, they’d vanish as quickly as they appeared. I started imaging what those creatures in the rock have seen. Four. Billion. Years. What they would think of these self-important creatures floating by, their minds cluttered with a hundred things that didn’t matter? What would they be saying to their rock friends about us?

Don’t they know how insignificant their eighty years here are?

It’s a shame they waste it worrying about what people think.

How they live small lives by talking themselves out of things because they might fail.

Don’t they realize how little time they have?

And how none of the shit they spend their lives worrying about will happen?

Or matter ten minutes after they’re gone?

Those wise voices were whispering exactly what I needed to hear. Not what I thought I needed, but what my soul needed.

It’s not about the answer, if there is one at all.

It’s about the questions.

It’s about starting, about moving.

It’s about trying.

My painful re-entry

I was wrapped in a peaceful, easy feeling as I left the woods on day five. It’s hard to describe. I still knew I was running out of time to do my best work, but it didn’t come with the stress of not knowing. I had found a comfort that everything would work out, even if I had no idea how. I just needed to keep going, trying to find ways to deploy my unique talents to be of service. I felt good about that.

But modern stress was coming, and it didn’t take long. As I drove south back into the city, that weightless feeling gave way to something more familiar. Dusty, rural roads turned into congested highways, and I could feel the collective stress of the drivers around me. We’re so used to it, we don’t notice it. But coming from the woods, I could sense the collision of these two worlds with every kilometer. And my body was starting to absorb it. Someone in a BMW cutting across three lanes of traffic to get fifty feet closer to wherever they were going (it’s always a BMW). The Hummer creeping up six inches off my back bumper. I almost gave someone the finger more than once. Almost. But it was close, closer than I want to admit.

What the hell was happening? What happened to Tranquility Bob? Is he really that fragile? How disappointed would the queen in the rock be right now?

The truth is, it is indeed a fragile peace I found. I know it’ll take practice every day to keep it breathing. I could feel it even as I walked into my house - the stack of bills sitting on the kitchen counter. The pile of dishes in the sink. Worlds were colliding, and I know which one is going to win, eventually. Because it always wins. The world is engineered for it to win.

But I’m not giving up without a fight.

Where I landed

I’ve been back less than 24 hours. I haven’t opened email. I haven’t checked social media. That doesn’t make me a hero, but I can feel the pull of it and I’m paying attention. I wanted to write this post while I still felt it in my bones, before it was nothing more than some quaint, hippy notions that my busy life forgot. I want to heed what the queen of the rock was whispering.

You tiny, simple canoer…

All that matters is the small group of people around you. Your people. That includes family, your close friends and a handful of close friends you haven’t met yet. The hundreds or thousands of people you are “connected” to on social media do not count. Do not spend another second of your short time here worrying what they think.

Nothing you do really matters that much. Nobody cares nearly as much as you think they do. There will be strangers living in your house a hundred years from now that have never heard your name. Or your kids’ names. If you have something you’ve always wanted to do, try it. Just once. You’ll probably fail. Good for you. It really doesn’t matter. But you’ll take your last breath with one less regret.

Stay curious. Ask questions. The purest version of your soul is the five-year old you. The playful kid that painted with every colour in the palette. The kid that didn’t know any better but to flail and to jump and call it dancing. The child that didn’t know they were supposed to care what anyone thought, let alone sculpt their life around it.

I’m loving this calm urgency I’ve found. This comfort in the not knowing. This peace in the continuing search to be of service, knowing I may never find what I’m looking for.

As my canoe-mate Peter said some time on day three…

Be kind. Be present. Keep paddling.

Shit, could it really be that simple?

If you’re thinking, not me - good for you. Maybe you’re right. It’s not like I felt scared my whole life. It’s only looking back at a life of questionable choices and bad habits have I realized oh yeah, of course it was all driven by fear. I was afraid of blending in, but also standing out. I was afraid of being seen, but also being forgotten. It’s a goddamn mess really. But it’s getting clearer. And maybe hearing me fumble towards a better understanding of my life will help clear the fog of that next thing you’ve been struggling to find.

You don’t have to be sober, but it helps

When I first quit drinking, I made a list. It included things I thought I could still do, and things I’d never do again. The first list included hanging with friends, going to the cottage and watching sports with the boys. These were things that always had alcohol involved, but that I could imagine myself still doing sober. The second list included things that were so booze-soaked, they simply couldn’t be done sober. Even if I could go through the motions, I didn’t see the point. These were drinking events disguised as respectable getaways that most modern men recognize. They included boys’ cottage weekends, trips to Nashville and fishing trips.

I did my first boys’ weekend about two years into sobriety. Everyone was drinking but me. It was weird at first, but I settled in. I quickly realized what I was most anxious about was making other people feel awkward. Nobody wants a sober narc hanging around trying to be one of the boys. I never trusted people like that. You’re either with us, or you’re against us. You need to be a part of this so I know you won’t tell your wife what really goes on here.

They say nobody spends as much time thinking about us as we spend worrying about it. It turns out nobody gave a shit whether I was drinking or not. They might not have even noticed. The most interesting thing, which sounds like such a cliche, is that it was actually more fun being there sober. And trust me, I’ve had a shit ton of fun on these weekends. I don’t care what anyone says - being irresponsible and acting like there are zero consequences to anything you do is a lot of fun. But being coherent and walking to two legs all day long is also fun. That first boys’ weekend was my first inkling that maybe this sober thing wasn’t so bad, and maybe there are other things I’ve been afraid of I should try.

All the things I thought I’d never do

Since then, I’ve done a bunch of things sober I thought I’d never do. I’ve gone to concerts, big and small. I’ve gone to bars and sporting events. I’ve gone to weddings and funerals. These are things I have not done without drinking since I was 17. I don’t even remember what it’s like going without a few drinks in me before I arrived, and then a bunch more. I had to relearn how to get comfortable in my own skin again.

My latest adventure was a fishing trip up north with some friends, my two sons and a bunch of their friends. I’ve gone on fishing trips before, and here’s a secret: fishing trips are not about fishing. They’re about drinking, boating and fishing - in that order. So ok, maybe I am a bit of a narc now. A fishing trip was at the very top of the list of things I never thought I’d be able to do again.

It’s hard to put into words how I feel about the trip. I had tears in my eyes for most of it, watching my kids bomb around islands and bays with their friends fishing, laughing and having beers. And I made this happen. Sure, I could have done it when I was drinking, but I’d have been a mess. I never want my kids to see me like that, and the idea of embarrassing them in front of their friends brings a different kind of tear to my eye. It was, hands down, one of the best weekends of my life. And I know they’ll remember it long after I’m gone.

None of it was ever real

Which brings me back to my list of things I never thought I’d be able to do again, because there is virtually nothing left on it. I haven’t done all the things I said I’d never do, but I’ve now realized the list was bullshit all along. It wasn’t a list of things I’ll never do. It was a list of fears - fears I have now overcome. It was a list of stories I had told myself - stories I have now rewritten. So even the things still on the list I haven’t done have no weight anymore.

Every one of has a list like this. It took me getting sober to actually make my list, but most of us carry one around without realizing it. We have a list of things we used to do, or have always wanted to do, or have put off so long we’ve forgotten about. And it’s all bullshit. It’s a list of fears, of old stories that have been there so long they become part of us. I never set out to break down my list one item at a time. It just happened. I did one thing, and the next thing didn’t seem so insurmountable. Until I realized none of it was ever real.

And therein lies the magic for you, if you’re willing to embrace it.

You will always be scared.

You will never feel whole.

You will never be ready.

You just have to start. Maybe the fears that held you back your whole life never go away. But they subside, resurface smaller and eventually lose their weight. And yes, new fears will show up, but not to stop you.

Instead to whisper,

“Go on. Be unstoppable. I fucking dare you.”

The paradox of retreats

I am a big fan of these retreats, at least the two I’ve tried this year. If you told me five years ago, I’d be going on multiple retreats a year, I’d say, what the f*ck for? But they’ve been nothing short of transformational, and I bet some kind of retreat would be helpful to you. And therein lies the paradox. These experiences are necessary in the world we live in. And it’s crazy that we need them. It’s bizarro world. Retreats give us a chance to reconnect with the way that our brains and our bodies and our physiology have been designed. It’s the way we’re supposed to live. But because of the lives we’ve chosen, full of technology that keeps us disconnected from ourselves and one another, we’re willing to settle for three days a year.

In a perfect world, we would never need retreats. But unless you’re planning on selling everything to be a farmer, I don’t see that happening. The reason these experiences are so transformational is that they’re in such contrast to our normal lives: completely disconnected from technology, having vulnerable conversations, and exploring questions we’ve never asked ourselves. For me, it was jarring because that version of myself, that part of me that I rediscover, doesn’t seem to be able to survive in this normal world.

I want to create a balance where retreat Bob and normal life Bob can live in harmony. I want to smooth out the edges between my retreat experience and my normal life so it doesn’t feel like I’m living on another planet for three days, only to go through a painful re-entry back into real life.

A tale of two retreats

First, let me provide some context. My first ever retreat was about then months ago at Waypoint, run by Greg and Whitney Boyd from Vienna Waits. They’re both friends of mine who I’ve had on my podcast to share their stories. Last year was their inaugural retreat and they asked me to do the keynote. It was amazing. Lots of laughs and tears. Every retreat has a theme and Waypoint is all about helping entrepreneurs and aspiring entrepreneurs turn their inspiration into action. It’s three days in a beautiful glamping resort a couple hours outside Toronto, with about 20 people trying to do the same thing. If that sounds like you, I’d seriously check it out (and I’ll see you there in September).

The second retreat I did was about a month ago at Heartstrings Songwriting Retreat, put on by Peter Katz, renowned musician and speaker that I also had on my podcast last year. It’s for aspiring songwriters and after three days at his sprawling cottage, Peter promises that you’ll leave with a fully written and recorded song. It was incredible and Peter, along with his amazing supporting cast, delivered. After a lifetime of trying, I wrote and recorded a song in three days. It was an incredibly emotional experience. If you’ve ever thought you might have a song in you, you owe it to yourself to check it out.

The value of whitespace

The hosts of these retreats agonized over every detail of the experience, from the physical space to the connections and conversations that happen leading up to the retreat, everything that happens at the retreat, and even what happens as a follow-on to these experiences. Every detail is curated.

What I found most interesting is that the programming has lots of space in between. We come together as a group where somebody will introduce an idea or a framework we can use, and then we go away to reflect on it. You can go for a bike ride, journal, do yoga, work out, or you can start conversations with other guests about things you’re struggling with or things you have in common. They have struck just the right balance between the guidance and support that they provide in the programming, and the white space in between for everyone to explore those ideas on their own.

We’ve all been to corporate retreats with three days packed full of meetings from 8am to dinnertime. Everybody leaves hungover, overwhelmed and exhausted. This is the opposite of that.

And that is the beauty of it - and the part that is a bit hard to reconcile - because it feels like I’m paying a bunch of money to sit by myself on a rock and listen to the wind in the trees. I don’t want to trivialize these experiences because they are so much more than that. But also, that is the magic of it. A bit of inspiration from the group. Some ideas on how to get started. Maybe a guide on where to start. Then time alone to digest, reflect and make it your own. The programming part is something you could conceivably get anywhere. ChatGPT could do give me a plan to transform my business. It could give me a five-step process to write a song. That’s the easy part. But it’s the conversation around it, the time to digest and reflect - and getting that cocktail just right - that you’re paying for.

The neuroscience of all this

I recently devoured, The Meaning of Your Life, by Arthur Brooks. Brooks is a Harvard professor and researcher on happiness, fulfillment and meaning. One of the things he explores in the book is the difference between complicated problems and complex problems.

Complicated problems are technical ones, like how do I do A, B or C? How does a jet engine work? How can I build by business to $1M? These are problems that technology and AI help us solve. And we have filled our lives with apps to make answering these questions easier. We have gotten much better at solving complicated problems.

Complex problems are unknowable, they don’t have answers. They require us to get deeply curious and creative. We can explore these problems conceptually but we will never truly understand them. Because there is no answer, we will never find what we’re looking for. They force us to seek enjoyment in the journey because there is no satisfying destination. These questions relate to love, happiness, and the meaning of life.

The left side of the brain - the what and the how - is really good at solving complicated problems. But our reliance on technology means we are spending all our time in our left brain. We are always working, hustling, being more productive - and we have never been more empty, alone and unfulfilled.

Similarly, the right side of our brain - the why - the part that is designed for complex problems, is atrophying. We spend our lives on our phones solving complicated problems and are forgetting how to sit, to wonder, to contemplate the unknowable. While these problems are unsolvable, their pursuit is the key to finding fulfillment, happiness and connecting with ourselves and others.

This explains why we’re so uncomfortable in quiet, being by ourselves. We have this compulsion to always be doing something, always be listening, always be learning, always be productive. We listen to podcasts or audiobooks while we’re folding laundry, exercising or driving. Because it feels like wasting time letting our minds wander. But being quiet, being by ourselves, is not wasting time. It’s where the right side works. It needs space to think. And we’re smothering it in digital slop that consumes every minute of our lives.

Viewed through this scientific lens, it explains why retreats are so jarring. They force us to use the right side of our brain that has been sitting there unused. Most of the experience is spent trying to quiet the left ‘bully’ that’s been getting all the attention, while nurturing the right side that’s weak from not being asked any questions.

To go deeper, check out the latest episode of the Growth Mixtape

Stop trying so hard

I did some thinking in the days leading up to Heartstrings on what I might write a song about. I came up with some decent ideas, and maybe they’ll become songs someday. But the first thing I learned is that it’s not up to us what we create. It’s our job to be open, to notice. Every one of the four songwriters there came armed with ideas, and every one of us wrote about something else we were inspired by while we were there. And our songs were more personal, emotional and vulnerable because of it.

And that’s a perfect illustration of the left and right brain at work. I needed some ideas for the retreat - a solvable problem - and my left brain delivered. But it was only when I disconnected from the noise of my life and gave my right brain time to breathe, did inspiration find me in the form of a song I would never have come up with trying so hard. This is the magic of reconnecting with that part of us we’ve lost in our normal lives.

So maybe you’re not trying to write a song. But everyone has questions they wrestle with - about a job that doesn’t light you up like it used to, relationships that seem to have run their course, or a restless feeling you can’t shake that you were meant to do more with the time you have left. My question for you is, what if you already know the answers? Isn’t it worth trying to quiet the noise in your life so you can hear them?

For me, and the people I’ve talked to, I know there is truth to this. I believe the answers to the problems keeping us up at night are on the other side of all the distractions and comparisons and anxiety we’ve built into our lives. What we’re looking for is just under the surface, hidden for so long we don’t recognize it when it does show up.

Bringing retreat Bob back here

For both of these experiences, I went into the woods looking to do a specific thing. At Waypoint, it was to build momentum towards a new business. For Heartstrings, it was to write a song. In both cases, what I discovered in those three days is something I didn’t even know I’d lost. I found the very best version of myself - honest, vulnerable, brave and unapologetically myself.

I want to bring that version of Bob back here to the real world. I’ll be honest, I don’t know how long he can survive here. This place, with all its distractions and fake authenticity, is engineered to murder that truest version of us. But I know the answers I’m looking for are inside me - not out there in more followers, more money or bigger audiences.

So as you save up for that next retreat and circle the dates on your calendar, remember what you’re really doing. You’re settling to live for three days, the way you’re wired to live all the time. In nature, with the water and the trees and the turtles and the hummingbirds. Connected with ourselves, our bodies and with other people in person.

And listening - to that voice inside us that loves us and knows what we’re really capable of.

About a month ago, I applied to speak at an event a couple hours from here. I actually heard about it from my friend, Michelle, who also applied. We talked about how much fun it would be to drive there together, and make a day of it. This week I sent her a text saying, I guess we didn’t make the cut, since I hadn’t heard back. She replied saying that she did hear back, that she was accepted. An hour later I got a nicely worded email from the conference saying thanks, but no thanks. I’m no stranger to rejection, it’s a part of the business. But it always stings. Still, I responded to Michelle with something supportive, something a much better version of me would say and actually mean it.

I’ve been paying more attention to these moments, how often they happen and how much they affect me. I’ve had good things happen to friends and colleagues that really bothered me. But the worst part is always the self-loathing that comes with it, because I don’t want to feel this way. It’s the cognitive dissonance between the way I feel and the way I want to feel - the way any good friend would feel. I have this image I want to project of this person cheering everyone on. It’s who I genuinely want to be. I just don’t always feel it. And it’s a terrible feeling.

The science of being happy for people

I’m trying to be gentle with myself. I can’t be the only one feeling this way. I’m really not a sociopath. I genuinely care for people, and I do want everyone around me to succeed. So what is going on here?

The science of persuasion and motivation has always fascinated me. I took a bunch of psychology classes in university and my favorite part was learning about all the unconscious biases we hold - these things that work below our awareness that explain why we do things or feel a certain way. And the one that stuck with me more than any other, is called the fundamental attribution error.

I purposefully did not google it, because I’m not interested in the textbook definition. I never let the facts get in the way of a good story. Here is what I remember from that psych class 20 years ago:

• We tend to attribute good things happening to other people to their environment. For example, when a colleague gets a fancy new job, we automatically assume it’s because of luck or circumstance - in other words, things that happened to them, not anything they did.

• We tend to attribute good things happening to us to our character. So, if we get a fancy new job, it’s because we worked hard and deserve it.

• And the opposite is true for bad things happening. If we see someone running a red light, we automatically call them an asshole for endangering the lives of everyone around them. We attribute their bad behaviour to their character. But when we do it, it’s something in our environment that made us do it. I’m sorry, I really need to get my kid to the rink on time. or he’ll get taken off the power play.

I’m sure there is an evolutionary advantage to feeling this way - that’s the only way any of these unconscious biases survive this long. It’s another way our brains protect us from things that could harm us. So when good things happen to people around us, it’s not natural for us to be happy for them. Because deep down, we resent them for being lucky, while all our hard work goes unnoticed.

Tech bro’s pretending

I recently had Greg Boyd on my podcast and we got pretty deep into this. We met working for a big tech firm. We became friends, took a couple business trips together, and stayed in touch as we both went our separate ways. Greg left to work for another, cooler tech company. Then I left too. I became a VP, he became a VP. Even though he’s more than ten years younger, there was always an unspoken competition between us. We’d get together for beers occasionally and congratulate each other on all the amazing things the other was doing.

And as we uncovered on the pod, it was all bullshit. We were never happy for one another. We just never said it out loud until now.

Listen to my full conversation with Greg

There is hope for me, and you

Rest assured, I don’t always feel this way. There are plenty of times I don’t have to fake it, when I am genuinely happy for people when things go their way. That jealousy I feel has everything to do with me, and nothing to do with them. And this is what I’ve learned.

1. When I have momentum on things I care about, I don’t have to fake it.

2. When I’m clear and focused on helping people, I don’t have to fake it.

3. When I’m feeling confident I’m doing something I am uniquely wired to do, I don’t have to fake it.

Momentum, clarity, confidence. When one or more of those things are missing, or God forbid all of them, I am going through the motions going nowhere important. I feel like I’m wandering around in the fog, unsure what to do next. And when I see other people around me succeed when I’m lost, I resent them for it. All me. No them.

And that’s precisely why I know this is more common than anyone wants to admit. Because that restless feeling I just described, is how everyone I talk to is feeling right now. And if you’re still reading this, I bet you are too.

So now I’ve learned to use these feelings for good, as a signal I can act on. When I don’t feel happy for other people, or am quietly taking comfort in something bad happening to them, I stop. I ask, what is going on right now? Does the work I’m doing help people? Am I confident I can do it better than anyone else? Am I moving in the right direction? As long as I’m paying attention to those three things, I am hopeful - for myself, and for other people.

My happy ending with Michelle

As I was pretending to be happy for Michelle and feeling like a terrible friend for it, I got a DM from someone on LinkedIn. She said was having a hard time - there were some changes happening in her company, and she just finished letting someone go. She went onto say it was a recent episode of my podcast that helped her through it, that it made her feel less alone. I might have cried a little. Podcasting can be lonely - you don’t often hear from people. When someone takes the time to share how something I said helped them, it affects me deeply. And this one came at just the right time. I took a screenshot of it, and even thought about including it here. But I don’t want people thinking every time they say something nice it’s going to end up on Substack - even anonymously. So I hope she’s reading this.

Listen to the episode that helped her

As I was wiping the tears from my eyes, any lingering resentment I felt towards Michelle for being accepted while I wasn’t, vanished. That tiny bit of validation reminded me I am making a difference. I am good at this. I am moving in the right direction. We all need more of these external signals than we want to admit. Confidence is a fragile thing, and we never outgrow that.

So next time you feel yourself relishing a little too much in the misery of people you want to cheer for, don’t beat yourself up. Instead, use it as an opportunity. What is taking a toll on your confidence? Are you clear about what you’re doing and why? And do you have even the tiniest bit of momentum to feel good about the direction you’re heading?

The person you want to be is on the other side of those three things: clarity, confidence, momentum. When we have it, being happy for people comes naturally. It’s not the competition we tell ourselves it is.

There is plenty of room for everyone to thrive.

Despite all that, one thing has eluded me - writing a song. It’s always seemed like magic, something just beyond my grasp. When I finally did it after decades of trying, I found it surprisingly easy. What I learned has changed me. And you don’t have to write a song for it to help you too. Because it’s not really about that - it’s about stripping away the distractions that keep us from listening to that inner voice that knows the answers to the questions that keep us up at night. It’s about reconnecting with ourselves, with nature and with the people around us in an increasingly lonely world.

Rediscovering my creativity

My grandfather bought me a guitar for my 9th birthday - he wanted me to learn bluegrass like Tommy Hunter on TV (I never did, sorry grandpa). I’ve played cover songs around the campfire my whole life. But one thing I’ve never been able to do is write something of my own. God knows I’ve tried. I’d write a couple lines, look down at the page and think, that is not as good as anything Tom Petty wrote. And I’d quit. It’s not that I’d write a song and throw it out. I’d never even get that far.

Making something from nothing, for no reason other than to express something inside us, is what makes us different than every other living thing on the planet. Creativity is what makes us human. But it gets dulled over time, buried under years of self-doubt, imposter syndrome and the fear of judgment. It’s that fear that kept me from writing a song, feeding that part of me that didn’t think I had anything interesting to say. The part of me that saw the words on the page and quit before the end of a single verse.

A little help from my friends

I was introduced to Peter Katz when he spoke at an event held by a local startup incubator I work with. He lit up the place. He seemed like a guy that had this creativity thing figured out so I had him on the Growth Mixtape Podcast to talk about his upcoming album, his creative process and what I might be able to learn. When he started talking about his Heartstrings Songwriting Retreats, it sounded like he was speaking directly to my soul. So, I circled the date on my calendar.

I was genuinely scared. I don’t know if Peter explicitly promises that everyone will leave with a song, but I know it’s never not happened. I was convinced I would be the one to break his streak - that I’d be the one on Sunday with nothing to share. I’m proud of myself for going through with it, because the Bob from five years ago would have come up with a dozen reasons to do something else that weekend.

The retreat was three days of quiet time for reflection, conversations with the other songwriters, and 1:1 sessions with Peter and his brilliant partner in crime, renowned musician and producer Rob Szabo. If you’re ever been in the presence of people that have somehow found exactly what they were put on this planet to do, you know how it feels. They made every one of us believe we had something inside us no one else in the world could make. When I laid my head on my pillow on Friday, I knew - for the first time in my life - I had a song in me.

Inspiration will find you

I did some thinking in the days leading up to the retreat on what I might write a song about. My son’s illness, growing old and irrelevant - some solid rock and roll ideas. And maybe they’ll become songs someday. But the first thing I learned is that it’s not up to us what we create. It’s our job to be open, to notice. Every one of the four songwriters there came armed with ideas, and every one of us wrote about something else we were inspired by while we were there. And our songs were more personal, emotional and vulnerable because of it.

When I look back on how the song came together, I couldn’t tell you how it happened. But I do remember one breakthrough moment. During one of the sessions with Peter, we discussed some of our favorite songs - the rules they followed, and the rules they broke. The song I chose was Angel from Montgomery by John Prine. The Bonnie Raitt cover is the song my wife and I fell in love to almost thirty years ago. One of the coolest things about it - it’s written from the perspective of an old woman. I’ve listened to it hundreds of times, played it around the campfire a hundred more - but it suddenly took on a special meaning.

The journey that inspired the song

The week before, I moved my mom into a retirement home. It’s something all of us hope we never have to do. But she can’t live on her own anymore, so we found a place we think she’ll be happy and safe. She had been living with my sister five hours north of here for the last year - so once we had her room all set up, it was my job to go get her. My mom has dementia, and as hard as it is to admit, I was not looking forward to five hours of answering the same questions over and over. Then my son had an idea - why don’t you make grandma a playlist? Kids come up with the best ideas. Some of my fondest memories are of my mom singing along to the radio - cleaning the house on Saturday mornings, partying with friends down in our rec room or belting it out on long car rides to the marina where we kept our boat. I curated a list of songs I remember her singing and put it on as we started our journey.

From the very first note of the very first song, I saw a spark return to her face I haven’t seen in years. She knew every word. This woman didn’t know where she was going or how long she’d be there, but she knew the lyrics to every song on that playlist. And for that entire ride, she was sixteen again. I was a beautiful moment, and I’m forever grateful for those hours we had together. It never occurred to me it might be a song someday. But it’s the song that was waiting for me.

Your creativity is waiting

So how did this happen? How did I get a song out in three days after trying for forty years? In some ways, it’s the easiest thing I’ve ever done. In other ways, it seems impossible in the world we live in. Maybe you aren’t interested in writing a song. But everyone has questions they wrestle with - about a job that doesn’t light you up like it used to, relationships that seem to have run their course, or a restless feeling you can’t shake that you were meant to do more with the time you have left. The answers to these questions seem out of reach - they’re not. You have everything you need. They’re just on the other side of all the noise we’ve built into our lives that prevents us from hearing them.

Unplug and get outside. I know, you’re tired of hearing it. Worse - you know it. You know how good it feels when you go into the woods and are forced to disconnect. So when is the last time you did it? I don’t mean just from email or Slack or LinkedIn. I mean from everything - texts, social media, all notifications. Arthur Brooks talks about this in his latest book, The Meaning of Your life. The right side of our brain, the part designed for wrestling with unknowable questions where true creativity lives, is atrophying from lack of use. We need to be bored. The only reason my song appeared is because I was present, with the turtles and the hummingbirds and the loons, and the water and the grass under my bare feet. Then I listened. I noticed. I paid attention. And it landed in my lap. I have more songs in me, but none of them will see the light of day from behind a screen. And the answers to your big questions won’t either.

Play with detached curiosity. One of our first exercises involved seven minutes of stream-of-conscious journaling. We did it out on the lake in Peter’s boat, but it could be anywhere in nature. The point is to write by hand and not stop. Look around and write about whatever comes to mind, no matter how silly or meaningless. It feels unnatural, but something shifts midway through. You move from struggling for something to say, to not being able to write fast enough. You’re learning to get ideas out of your head and onto the page without judging them. I wrote about what I saw, heard and felt. Some of it was nonsense. But every once in a while, something leapt onto the page, seemingly out of nowhere. I made note of it, and kept going. Without judgement, without thinking. Later, I took all my favourite lines and put them in one place. Then I picked a line, then another, and a story emerged out of thin air. This pure, detached curiosity is where the best ideas live.

Write a shitty first draft. I heard John Lennon talk about this. The problem most of us face is we come up with a good line or an idea and we jot it down. We plan on coming back to it later, but we don’t. Or we do, but the idea has lost its emotional charge. We forget what made it so meaningful. So it dies. The best way to combat this - finish the song, or the idea or whatever you’re working on. Keep going. It doesn’t matter if it sucks - in fact, it probably will. But now you have a shitty first draft to work with. Even if you throw 80% of it out, you’ve made it further than you ever have before. And you’ve captured the emotion that drew you to the idea in the first place. My finished song has lines in it I didn’t like at first. But I needed something. Now they’re some of my favourites - they just needed time to ripen.

Use constraints. The retreat was three days. Friday was writing day. Saturday was recording day. Sunday was listening day. I say I wrote a song in three days, but I actually did it in one. It needed to be locked in by Saturday morning, when it was time to step in front of the mic. If the retreat was two weeks, I would have spent ten days agonizing over every word. But it was good enough. And the song has a raw energy I would have lost by overthinking it. Constraints - whether it’s time, length, structure - allow us to focus intensely on something and then let it go. So we can move onto the next thing that requires our undivided attention.

Have conversations in 3D. There is a special place in heaven reserved for people that can foster a connection between strangers through pure intention and vulnerability. That is what Peter, Rob, Tessa and Ciaran did. We laughed and cried the entire time, and we’re bonded for life. Everyone felt safe to talk and explore things maybe some of our best friends don’t know about us. And through that safety came lyrics that would have stayed buried. You don’t need strong facilitators or a retreat to do this. You just need to step away from your screen and talk to people in real life. It’s how we’re built. It’s how we build trust and connection. And we all need more of it.

Now it’s your turn

I went into the woods looking to write a song. What I discovered in those three days is something I didn’t even know I’d lost. I found the very best version of myself - honest, vulnerable, brave and unapologetically myself. I finally know I have something to offer the world nobody else can. And in that knowledge I found the confidence to set aside all the fears and insecurities that have held me back my whole life. I want to bring that version of Bob back here to the real world. I’ll be honest, I don’t know how long he can survive here. This place, with all its distractions and fake authenticity, is engineered to murder that truest version of us. But I know the answers I’m looking for are inside me - not out there in more followers, more money or bigger audiences.

As we wrapped up the weekend, we talked as a group about going back to the real world and how we’d adjust. It’s a common conversation as people head back to their normal lives. Then Peter said something that stuck with me.

“That’s not the real world. This is the real world.”

We all have a song in us. An album. A lifetime of albums. Or paintings. Or stories. It’s in our bones and in our blood and in our skin. It’s our birthright. I spent forty years afraid I had nothing special to say. In three days, I created something no one else on earth could have made.

I can’t get the years back I wasted being afraid. But now I can’t help but wonder. What else have I been telling myself I can’t do, that is just a story I made up?

Maybe I really am invincible.

Want to learn more about Heartstrings Songwriting Retreats? It’s all right here.

It’s not nearly as bleak as it sounds. I am going to give you some language for what you’re experiencing and even a path to find your way through it. How do I know all this? Because I’m right in it with you. This post is the culmination of ideas and experiences I’ve gathered from dozens of conversations with leaders and friends. But it doesn’t happen without the universe throwing a new source of inspiration my way from an unlikely source.

So let’s start there.

What to make of a life

Have you ever read a book that feels like it was written specifically for you at just the right time? It first happened to me about five years ago when I read, A Creative Act by Rick Rubin. It was exactly what I needed as I embarked on a journey of rediscovering the creative spark I lost when I was a kid. Now, it’s happened again with, What to Make of Life by Jim Collins, except this time it’s not just written for me. It’s written for me and everyone else I talk to that feels stuck between the thing they’ve been doing for 20 years and the “something else I was meant to do” they haven’t discovered yet. I’m guessing that might sound familiar.

Jim is a very big deal, having authored some of the most notorious business books of our generation with Good to Great, Built to Last and Beyond Entrepreneurship. He has a a unique research approach where he pairs subjects, normally companies or leaders, through their evolution to pinpoint the critical differences that led to superior performance. In his latest book, he applies that methodology to people to understand how they built the lives they did, and what we can learn as we try to make the most of our time here. It’s not self-help - there is no prescriptive framework to follow on how to live a better life. What it does do is give us language to better understand how the experiences of our lives have uncovered the things we’re uniquely gifted at, and how to organize our lives around those. For people like me struggling to understand how to translate 20 years of experience doing one thing into something different that fuels my inner fire, it’s just what the doctor ordered.

Your constellations of encodings

The book doesn’t concern itself with the idea of purpose, which is a huge relief. I’m tired of that topic. I have a feeling if I had a purpose I would have found it by now. Or maybe I’m trying too hard, and as soon as I stop searching for it, it will appear. Instead, Jim introduces the idea of encodings, which are durable and intrinsic capabilities discovered through the experiences of life. They are not strengths we have cultivated or skills we have learned. We are born with them, and they are fixed. Think of encodings as stars in the sky. They can be grouped into constellations and each of us has a unique blend, and that special combination of constellations defines us. Nobody has the same combination of encodings. And we have more encodings than we will ever discover.

Maybe the thing that resonates most right out of the gate is this idea that we all have a unique set of innate capabilities no one else has. I think each of us feels that we do, but every time we try to articulate what makes us special, it ends up sounding like millions of other people out there. And the main reason we can’t convince anyone that we’re different is that we don’t really believe it ourselves. We look around at a sea of other successful people that look just like us. So we start to believe we’re good, but nothing special. And we feel restless and lost because we don’t know what we are meant to do, and where to start. The idea that we all have a set of unique encodings means we really do have something to offer the world no one else can. What is it? Well, we’re not there yet. But this alone feels like a comforting revelation.

It also provides hope for those of us that have been doing something for so long, we don’t know what else we’d be good at. Encodings are endless, and they are revealed through the experiences of life. The ones we’ve relied on until now are only the few that our lives have required of us. There are hundreds of other things we’re naturally wired to do. The study shows that of the 34 subjects in the book, most of them did their best work in their 50s, 60s, 70s and even 80s as they discovered new encodings later in life. Our best work really does lie ahead of us, as long as we can get unstuck from the mindset that what we’ve done until now is all we have to offer.

Over the cliffs and into the fog

Think back about the moments in your life where something happened that knocked your life off track. Cliffs can be good or bad, but you don’t usually see them coming. The first ones that come to mind for me are my parents divorce at 20, my dad dying 3 years later, meeting my wife, having kids, getting fired - twice, getting sober and almost losing my son. Every life has cliffs - some big, some small. How we respond to these cliffs and the decisions we make in their wake largely define the path our lives take. And they are often how we discover new encodings, as life knocks us out of our normal routine and requires we do something dramatically new. If you think back about times you uncovered new skills you didn’t know you had, I bet it wasn’t something you enthusiastically chose as much as something you did because it had to be done, and there was simply no one else around to do it.

Then there is fog - periods where we feel lost, disoriented and confused about what to do next. Fog often follows cliffs and everyone, no matter how accomplished or successful, finds themself in the fog sometimes. These fog funks can last months or years. People in the fog might look like they have it together on the outside, but inside they’re riddled with insecurity and fear.

I wonder how this description of fog sits with you right now? Because when I first read it, my reaction was visceral. Oh my God, that’s me, that’s everyone I talk to! The idea of being confused and anxious, specifically about what to do with the remaining years of our careers, perfectly describes what we’re all feeling. It’s like we’re all lost, stumbling around in the fog together. Everyone else seems to have life figured out but us, so we feel alone with no one to talk to about what we’re going through.

The fog of The Corporate Reckoning™

It is not normal that we’re all lost in the fog together. It’s a bit like a collective midlife crisis, except that I’ve talked to as many people in their 20s and 30s going through this as I have people like me in their 50s. What we’re experiencing is something I’ve called the corporate reckoning, the compounding effect of Covid, growing economic instability and AI. It explains this restlessness about the future people are feeling, and why what they’ve always done has stopped working. Everything has changed so fast, and continues to change, people feel like strangers in careers they’ve spent their lives building. And they’re left wondering whether this new world still needs the things they’re good at. The corporate reckoning is a very specific type of fog we’re all stuck in together. If you want to learn more about it, check out this post.

The corporate reckoning is not all doom and gloom. It presents people that understand what’s going on with a unique opportunity to proactively take control of their careers and get a leg up on everyone else that stays stuck in the fog. It means embarking on a kind of renewal that finally aligns your work with what you’re uniquely gifted at, what nobody else in the world has to offer but you. And in process, it offers the promise of fulfilling work that feels like it was made just for you.

Stepping to the other side

Jim’s book is unapologetically not self-help. There is no prescriptive roadmap to follow because providing one would fly in the face of Jim’s entire premise - that everyone’s encodings are different. Any advice anyone offers, while well-meaning, reflects their unique encodings and experiences - so is unlikely to work for you. In fact, it’s just as likely to send you down rabbit holes that make you more frustrated and confused.

That said, I have some ideas I’ve been testing with people I talk to. The results so far are promising.

1. Excavate your life - With this new language in hand, go back through the experiences of your life. Create a story bank, made up of cliffs and periods of fog. You’ll immediately be able to come up with a list of 5-10, but as you continue your excavation, more will come. Keep going.

2. Identify your frames - Imagine you’re looking at your life through a telescope. At any one time, you can only see a subset of stars and constellations in your frame. Everything else is out of view. There are times where you have a bright set of encodings in view, and you are in-frame. Work is easy, you lose sense of time. You work long hours not because you have to, because it’s what you love to do. There are also times when you are out-of-frame, where you can see very few stars or constellations. You’re not using your natural gifts, so everything feels harder than it should be. You can be wildly successful while out-of-frame, but you’re never fulfilled because you’re not doing work you’re hardwired to do.

3. Identify your encodings - With your list of life stories, and reflections on when you were in-frame and out-of-frame, start listing your encodings.

   1. What new encodings did you discover when cliffs through your life off-track?

   2. How did you find your way out of the fog? What encodings did you find?

   3. When you were in-frame, what were you doing? Who were you with? Where were you?

   4. When you were out-of-frame, same thing. These are your anti-encodings.

   5. What would you do, even if nobody ever knew you were doing it or paid you to do it?

4. Re-write your story - You’ve now got all of the raw materials you need, and it’s time to rewrite your story - one that finally sounds like you, completely unique from anyone that’s ever lived or will ever live. You’ll never have just one story. You can put together these Lego blocks together in an infinite number of ways. You might eventually have a story for LinkedIn, job interviews or prospective partners in something you build of your own. But the first story is just for you - the central story that you can finally believe in. You can check out mine below for inspiration.

5. Get curious - You’ve already gotten deeply curious about your life, your encodings and what makes you special. Now it’s time to turn that curiosity on the rest of the world. Go out and test out your story with people you know, and share the journey you took to get there. I guarantee people will be amazed at how compelling and memorable it is - how you it is. Start getting curious about the kinds of work, companies, roles and opportunities that make you a perfect fit for your unique set of encodings.

Examples from Bob

If this is feeling inspiring but a little abstract, I get it. I am a work in progress just like you. If it helps, here are just some of the encodings I’ve discovered and my central story so far.

Bob’s encodings

• I work best in the early morning.

• My best ideas come when I’m outside, near water, exercising or doing manual labour.

• I am most energized in 1:1 conversations and small groups.

• I like crafting stories and sharing them with larger groups.

• I love deeply understanding the root causes of issues people are having and exploring creative solutions.

• Despite believing I was not creative my whole life, I have 55 years of pent-up creativity inside me. I’m most fulfilled when I get it out and share it.

• I am told I make people feel heard and understood.

• I love exercising my curiosity to understand how people see the world differently than I do.

Bob’s central story

I played small my whole life, working hard to blend in instead of standing out. I was Art Garfunkel, content with 2nd place. Then in two short years, that changed. I got sober after a particularly embarrassing Easter weekend, and my son was rushed into surgery to remove a mass on his brain. I don’t know if my renewal happens with just one of those events, but I know it doesn’t happen when it did, or as quickly, without that combo.

Sobriety unlocked my curiosity, and brought clarity on what I’m uniquely gifted at. And almost losing my son instilled a sense of urgency to do something more with the time I have left. I believe curiosity can save us from the mediocre lives we’ve been settling for and I’m on a mission to help a million people rediscover their curiosity and live the bigger lives they deserve.

C’mon, you have to admit that doesn’t sound like anyone else you’ve ever heard. It could only be me.

Now it’s time to go tell your story.

I assure you, the world still needs you - maybe now more than ever. The mistake people make is thinking that their skills and experience is what sets them apart. You’re good at building relationships, getting the most out of teams, you’re a good listener. Sorry, none of that makes you special. There are millions of people out there just like that. In order to be able tell people why you’re different, you need to know it yourself. You need to not just think you’re different, not just believe you’re different. You need to know it in your bones, the way religious zealots know there is a heaven - or whatever. And the only thing any of us have that is ours - the one thing nobody who’s ever lived or will ever live has - is our story. That unique combination of experiences, mistakes and successes that define our lives. Understanding and communicating that story is all you need to stand out and show the world what you can offer that no one else can.

My story

I’ve been struggling with this for a long time. When you ask my clients or people that know me, what makes me different, you’ll hear I’m a good listener. I ask good questions, I am genuinely curious and I make people feel heard. Don’t get me wrong, that is awesome to hear and I’m very proud of it. But it’s never going to get me hired to speak at a conference or coach a leader for one simple reason. It sounds like everyone else out there. Talk is cheap. Anybody can say they’re good at those things. And if you write down all the things you’re really good at, uniquely gifted at, you’ll sound just like everyone else too. There is no point in blending in, not ever, but especially not at this stage of our lives. We need to stand out.

The good news is you have everything you need to tell your story in a way that people will remember. But before you can build it, you need to tear everything apart.

The excavation

The first step starts easy, then gets messy. It’s where we deconstruct our lives into pieces we can re-assemble later into a story that oozes with our awesomeness. Think of each piece as a Lego block. We can’t build our story until we get all the pieces spread out on the floor. This is the excavation.

Start by building a story bank, made up of moments that have defined your life. If I asked you to write down the significant moments in your life, you could probably come up with five pretty easily. They might include meeting your spouse, having kids, getting fired or losing a parent. Those are all good ones. You’re off to a great start. There is no right number of moments for your story bank, but the more the better. Trust me, the more you write, the most stories will start to pour out - including ones you’ve forgotten all about.

Once you’ve got the low-hanging fruit out, try thinking of moments in these buckets, taken from Jim Collins’ new book, What to Make of a Life:

Cliffs - The examples I gave earlier are cliffs - events, good or bad, that change the course of our lives.

Fog - Periods where you feel lost and unsure what to do next. They often follow cliffs. Maybe it’s a bit foggy where you are right now.

In-frame - Periods or moments when everything just clicks. You’re confident, you’re focused and you feel like you’re doing what you were meant to do.

Out-of-frame - Periods where you’re not miserable, but you you’re not fulfilled either. You know you’re not fully using your natural talents, and there must be something else you were meant to do.

Making sense of it all

Now look for patterns. Ask yourself these questions, and don’t rush them.

1. What else was happening in your life that made each cliff so impactful? What do they have in common?

2. What else was happening when you were lost in the fog? What did these moments have in common? How did it feel?

3. How did you find your way out of the fog?

4. When you were in-frame, what skills were you using every day? Who were you working with? What are all the variables, internal and external, that made it click?

5. When you were out-of-frame, what felt off? What were you doing that felt harder than it should have been? How did you find your way out?

Now you’ve got some Lego blocks to work with. You’ll also have insights you didn’t have before.

• Natural abilities you have that set you apart, and that you need to use every day to thrive.

• Types of work, environments and people that make you feel whole - and which ones to avoid.

• How each of these moments shaped you, and how that translates into what you can offer the world.

Most importantly, you can build your story from the ground up, rooted in meaningful moments that only you lived through. It’s a story nobody has but you.

Building your story

This is the fun part, but it takes time. You have so many Lego blocks to work with, you could tell a hundred stories. But the story to tell first is the one to yourself - the one story that paints a picture of why you are who you are. The one that makes you finally know in your bones what you have to offer the world no one else can - not because you have a unique set of skills, because you’ve lived a life no one else has.

I have a confession to make - I used AI to help me do this, but only after a lot of reflection on my own. I had Claude interview me for 4-5 hours over a week to get all my stories out. It’s exhausting and emotional, so whether you use AI, a pen and paper or something in between, I suggest spreading it out. Take lots of breaks. The best stories need time to surface. I prompted Claude to ask me about cliffs, fog and frames and to ask lots of follow-up questions. It forced me to go deeper than I would have on my own. Maybe you have a real friend to do this with - that would work too.

Then I asked Claude to craft 3 options for my story. I picked one, and rewrote it several times before I got it right. I even zeroed in on the last ten years, and had it generate a picture for me. These are the years I talk about most often when sharing my work story. If you’re artistic, I highly recommend trying this on your own. If you’re like me, this will stick in your brain more than a bunch of text will.

Where your story goes

Armed with your new story about what you have that no one else has, who needs to hear it? Well, that depends on what specific flavour of midlife crisis you’re having.

Feeling restless and unsure what to do next - Get out and practice your story. Talk to people in your network. Get curious and explore the types of businesses and roles facing problems you’re uniquely positioned to solve. Get out of your comfort zone. And talk to people that started their own businesses - maybe your story is telling you this is your time.

Stuck in a job that doesn’t fuel you - Use your story to evaluate your options. Can you get back in-frame in your existing job by re-focusing on what you’re naturally gifted at? If not, set a timeline to move on.

In the job-market - Update our LinkedIn banner, tagline and About section with your new story. And use it to get more specific about the work you go after.

Starting a side-hustle - If you’ve always wanted to try something of your own, does your story give you clarity on what that is, and what help you need? If you haven’t thought of it, why not?

Writing a book, starting a podcast, growing a garden - What else is possible, now that you have clarity on what fuels you and what you’re uniquely gifted at?

Here’s just one example of where my story took me. This will be a page on my new website. Until I had my story, this was a jumbled, confusing collection of loosely related ideas. Now the Lego blocks are assembled into something that looks and sounds just like me.

You’ve only just begun

The irony of this collective midlife crisis is how isolating it feels. We’re all lost in the fog together, but also alone, feeling like we have no choice but to find our way through it on our own.

You’re not alone.

You are different.

It’s not too late to do everything you’ve always wanted to do.

And soon, you’ll have the story to prove it.

First to yourself, then to everyone else.

If you just heard a little voice inside your head saying, “FCK THAT”, you’re not alone. Most of us have done the next obvious thing our whole lives, culminating in a career that looks pretty impressive on paper. We didn’t plan it, it just happened. But now, as we stand on the precipice of the last season of our careers, we can’t help but feel it’s our time to do something that feels more like us. If only we could shake the dread that we’re running out of time.

You’re not. Life is plenty long.

But you do have to get started.

Life is short doesn’t last

I don’t remember the first time I heard the phrase, “Life is short.” It’s such a part of our common lexicon, nobody remembers where it came from. Most of us don’t give it much thought, except at funerals. We sit there with our hands in our lap, trying to imagine what people will be saying when it’s us in that box. We swear to ourselves we’re going to start doing things differently. We’re going to prioritize our family. We’re going to tell people we love them more often. We’re going to write that book.

We’re going to live every day like it was our last.

But we don’t. That warm feeling doesn’t last. A week later, we’re back to waking up at 3:00 worrying about the same useless shit we were before - that email we forgot to send, that snarky comment on LinkedIn, the conversation we’re not ready for. The book we were going to write goes back into the someday pile. The I love you’s go unsaid. All the important things get lost again.

The next 25

Life isn’t that short, it’s plenty long. We might be on the back nine, but we still have 25 good years to make the impact on the world we want to make. I know that feels daunting. I can’t believe how fast the last 25 years has gone. But think about everything you’ve done in that time. Really think about it, write it down. Now, take a step back. It feels like three lifetimes. I bet you’re like me and barely recognize that person from 25 years ago. So what makes you think you can’t make just as big a leap in the next 25, armed with all that experience? You’ll make mistakes. You’ll recover. You’ll keep going. Because that’s what you’ve always done. You just have to stop telling yourself it’s too late.

You can start your dream business.

You can travel to far away places.

You can write a book.

Everything you’ve done up to now has prepared you for this. It’s put you right here, right now, for a reason.

Yes, life is short. That means you need to move.

And life is long. There is nothing you’ve always wanted to do that you still don’t have time to do.

Don’t let your primitive monkey brain fool you - it’s never too late. You have but one simple job. Get started now.

What sobriety taught me about time

I’ve been open about my sobriety. I can count on one hand how many weekends I took off drinking from the time I started at 17 to the time I quit at 52. 35 years of weekends - I haven’t done the math, maybe I don’t want to see the number. It’s big. And while I’m proud of myself and grateful I had the courage to do it, I’m left wondering what I could have accomplished with all those days lost to thinking about drinking, drinking and recovering from drinking.

It’s depressing when I think of how much more productive I am now and what I could have done. But I’ve learned to find comfort in the fact that I quit when I did and I didn’t lose any more days than I already lost. That’s got to be good enough, because I can’t do anything about the past. And that’s a lesson I’m learning to apply to other decisions I’ve been putting off.

Stop trying to make time

It’s funny how we think about time. The #1 reason most people cite when talking about things they’ve always wanted to do but can’t right now, is time. I don’t have time. I’ll do it in January when I have more time. I just need to get through the next couple of months and things will settle down. Then I’ll have the time.

Spoiler alert: you’ll never have more time.

Time doesn’t magically appear, and if you don’t have the time now, there is no reason to believe you’ll have it later. The phrase “make the time” is comically unhelpful - nobody can make time. Time just happens. It’s the one thing we can never slow down, stop or speed up. What we can control is how we spend it, right now. Because it’s the only time we know for sure we have.

Practical advice from an expert on time

The best resource I’ve found to help me make the best use of my time is Tim Ferris’ best-selling book, “The Four Hour Workweek”. It’s a masterpiece and I can’t do all the lessons and tools justice, you just have to read it. But here are some things that have stuck with me, and that I’ve actually managed to put into practice.

Build walls around your time

Tim talks about Parkinson’s Law in the context of time. It basically says that our work will take up as much time as we give it. An hour meeting will take an hour, even if we can do everything we need to do in 20 minutes. If we allow people full access to our calendars, it will be full of meetings. If we want more control over our time, we need to limit the amount of time we give to certain things.

Tim suggests no meetings on Mondays or Fridays, and no meetings after 4pm. I started this a year ago and it’s one of the few rules I’ve managed to stick to. I know you think all your existing meetings will just get squeezed into fewer hours, creating even more chaos. That’s not what happens. Prioritization happens. You’ll have fewer meetings, more freedom and somehow the work will still get done.

Don’t tell me it can’t work for you. Your time either matters, or it doesn’t.

Procrastinate smartly

Procrastination is not a bad word. I learned this lesson in school. If an assignment was due on Friday at 4pm, I’d watch people work their asses off and spend hundreds of hours on it over the weeks leading up to the deadline. I’d leave it until the day before, and spend 6 hours on it. Yes, they got a better mark, but not that much better. So they spent 20 times longer to get a 10% higher mark. I’ll take that tradeoff any day.

At work, time kills. The longer you plan something to take, the more people will change their minds or other things will come up to compete with the resources you need. If you give someone two weeks to do something, they’ll leave it to an hour before the meeting. So give them until tomorrow. Shorten timelines, confine the work into smaller pieces. And don’t do anything until you need to do it.

No email before 11:00 am

If you have more than one critical task each day, you’re trying to do too much. Most of us start our day with three or four. We rarely feel accomplished, and we live our lives in a perpetual state of feeling like we’re never doing enough. Even when we’re moving forward, we’re standing still.

Instead, ask yourself, if I did just one thing today to make me feel great, what would it be? It takes practice to stick to one. Then block two hours in your calendar to get it done, with no interruptions. Don’t open email or any other apps. Keep the world at bay. At 11:00, open the floodgates and deal with everything else that’s been thrown at you. By then, you’ve already done the only thing that matters.

We don’t use time, it uses us

We’re never going to stop obsessing over time. It only gets worse as we get older and realize how little of it we have left. I can’t do anything about the time I’ve lost to bad decisions, or good decisions I took too long to make. I can accept that.

What I can’t accept is the thought of looking back in ten years and realizing I had the chance to change and didn’t - that I thought it was too late, when I really had all the time I needed.

I think you know the answer. I talk to experienced professionals every day trapped in jobs they’ve lost their passion for, or struggling to stand out in a crowded job market. What always worked has stopped working. The career ladder we expected would always be there has collapsed. People aren’t reinventing themselves because they want to. They’re disoriented, lost and afraid. That’s no way to live. So, we can all get jobs at our local bookstore, and lie to everyone about how much happier we are now that we’ve rejected the evils of hustle culture. In other words, we can give up. Or we can take back control of our careers - maybe for the first time ever - and show this strange new world just how wrong it is about us.

What makes reinvention so hard?

Maybe you know people that changed careers and made it look easy. They didn’t go through an identity crisis. There was no reinvention. They simply quit one thing and started another. How do they do it? Why is it so much harder for the rest of us?

Because for most of us, our job isn’t just a thing we do for money - it’s our identity. When I was a VP of a growing software company, it was a big part of who I was. It was the first thing I said when people asked what I do. So when I got fired, I was angry and embarrassed. But more than that, I was lost. If I wasn’t a big deal VP, who was I? It didn’t matter that I was miserable and ready to quit. I was rejected, told I wasn’t good enough. It shook my confidence, and it took me years to get it back. It can still bother me if I dwell on it.

The only reason that rejection in our careers hurts so much, and why this journey of reinvention is so personal, is that we’re not just reinventing what we do for a living. We’re reinventing the image we have of ourselves and our place in the world.

Linear and spiral careers

Author Arthur Brooks talks about the difference between linear careers and spiral careers. A linear career is what we were sold by our parents, educators and society as a whole. These careers read like a typical resume - change jobs every 2-3 years and move up the ladder. Once you’re on a chosen path, you stick to it until the end. It’s how careers have always worked. It’s how ours were supposed to work.

An alternative is the spiral career, in which you pivot, or reinvent yourself, every 7-10 years. Each time you take it down to the studs, you recreate something new of your own design. Proactively. People with these careers have reinvention built in, so what they’re doing at any given time is not tied to their identity. If they get laid off or something else unexpected happens, it’s less traumatic. It was never supposed to be permanent anyway. These enlightened spiralers are continually exercising their reinvention muscle, as opposed to the rest of us who get forced into it by a world we feel no longer needs us.

We’re seeing the end of linear careers. There is no longer such a thing as going to school, picking one career and doing it until you retire. Things are changing too fast. Everyone will have 3, 4 maybe 5 mini-careers. Even teachers and nurses, who used to be the exception with the most linear of careers, don’t see themselves doing those jobs forever. We all need to get comfortable with spiral careers, which means being the architect of these reinventions every few years, so we’re not caught flat-footed and lost if and when disruption is forced upon us.

Inspiration from unlikely sources

I have been talking lately with a lot of people going through reinventions of their own, but that’s not what inspired this post. That came from a much more unlikely source - minor hockey.

I recently had on my podcast, who is a rockstar entrepreneur and overall badass. One of the topics we stumbled into was her experience being a hockey mom, and the unexpected grief she felt as her son’s hockey career came to an abrupt end from an ACL injury. That brought back a flood of emotional memories for me - my youngest son’s hockey career was also cut short when he had to undergo emergency surgery to remove a mass on his brain. He’s fully recovered now, but I didn’t realize at the time how much of a hole walking away from hockey would leave - in his life and in our relationship. In retrospect, I realize it’s all we really talked about. When he recovered, he was lost and so was I. If he wasn’t a AAA hockey player, who was he? And it wasn’t easy for me to accept the role I played in all his self-worth being tied up in how many goals he scored or how much time he got on the power play. I wish I spent more time making sure he knew he was so much more than a hockey player. Maybe then he wouldn’t have been so crushed when it all got taken away.

Listen to Whitney's Episode

Which brings me back to this epidemic of our identities being so tied to what we do instead of who we are. Here I am in my 50s, in the middle of my third or fourth reinvention, trying to support my kids through their first. Yet I feel woefully underqualified, since I seem only marginally less lost than they are. Maybe I have as much to learn from them, as they do from me.

Don’t call it reinvention

Perhaps the term reinvention is too traumatic. It certainly feels like a lot. Maybe that’s because it’s often done out of panic. Whether it’s being laid off, struck with a crisis of purpose as you near the end of your career, or even an unexpected injury in your teens, we reinvent ourselves because we’re forced to. Quick, find a new story, something new to say - rather than undergoing a continuous, proactive and thoughtful evaluation of what to do for the next 7-10 years. If we make this part of how we operate, we’re not reinventing ourselves as much as we are periodically self-correcting to make sure we’re making the best use of our talents, being of service and staying in demand.

This is not an academic exercise - we no longer have a choice. We might have enjoyed linear careers until now, but they don’t exist anymore. We can’t keep playing by the old rules that made us successful, because the game has changed. Knowing that should bring us comfort since if nothing else, it gives words to the betrayal we’re feeling.

And now that we know, we can get on with taking back control over the years we have left. It sure beats lying awake at night worrying about whether we still matter, and trying to salvage what we can from a career we no longer recognize.

The signals

Talented executives are being let go at an unprecedented rate. I bet you know some. Maybe you are one. Sure, layoffs come with the territory when the economy slows, but not like this. This time, it’s the rockstar leaders being let go, the ones with storied careers and decades of impressive results. They’re used to getting promoted, not fired. And they’re not getting snatched up when they hit the job market like they used to. They’re out there for 1-2 years before taking a role they once considered beneath them.

Here are some of the recurring themes from my conversations:

• I miss the days when I used to love my job. I’m out of energy, and answers.

• I used to be the one my boss came to for everything. Now there are more and more meetings I’m not invited to.

• I no longer feel the confidence on the inside I need to show on the outside.

• So much of my identity is tied up in my work. If I don’t do this, who am I?

• Is this really all their is? I feel like after decades of experience, I’ve earned the right to be more secure by now.

And we have data:

• 1 in 3 middle managers were cut in 2023. Not underperformers - experienced Directors and VPs doing everything right.

• 43% drop in hiring for senior managers since 2022. These positions aren’t being filled, they’re gone.

• 56% of leaders reported burnout in 2024. Half report significant loneliness. The leaders that appear to have it together are quietly falling apart.

So what changed? Did these leaders suddenly become less effective and less talented? Did they become irrelevant overnight?

No. And yes.

The Corporate Reckoning™

I call it The Corporate Reckoning, the compounding effect of the global pandemic, growing economic instability and AI. It explains everything leaders are feeling, and why what they’ve always done has stopped working. The good news is once they name it, it presents a unique opportunity to set themselves apart by addressing head on what nobody else sees. The bad news, they really have no other choice.

To be clear, this isn’t just for leaders that were let go. The Corporate Reckoning does not discriminate. While leaders with jobs can’t quite explain what’s happening, they’re suffering from a lack of confidence they haven’t felt in years. Everything is shifting around them. They barely recognize the job they’re in. It’s not one they asked for; hell, it’s not one they’d even apply for today. For them, the reckoning is about taking control of their careers while they still have a paycheque. Before someone makes the decision for them, and they’re caught flat-footed in a job market with a million other rockstars just like them.

Now, let’s take a look at how we got here.

COVID (2019-2021)

When the lockdowns happened, everyone got Zoom accounts and our calendars filled up with more meetings than we ever had in person. But we were in survival mode. We didn’t take the time to consider what we were losing with this new way of working because what would be the point? It’s all temporary anyway.

If you described your current life to a 2018 version of yourself, they’d look at you like you were from outer space. Nothing short of a global crisis, in which our very survival was threatened, would ever force us to change this quickly. A new normal emerged that we never designed - it’s simply where the pendulum came to rest. And now here we are - stuck in jobs we never expected, asked for or wanted for ourselves.

What leaders didn’t realize right away is the things that made them good were gone. The informal infrastructure of leadership disappeared overnight.

• The hallway conversations where decisions actually got made.

• The lunches where alliances were built.

• The after-work drinks where we could be honest about what wasn’t working.

Any honest leader will tell you, their success is due to the people around them. Their contribution is getting the best out of people, and getting them to work together. But the relationships that used to form organically now require deliberate effort that nobody has time for.

More importantly, spending our days in virtual meetings has stripped our lives of the connections we relied on to give our work purpose. There is no joy in it anymore. The sense of community is gone that helped us through the rough patches, because we always knew we were in it together.

AI and economic contraction (2022-2024)

Before leaders could even adjust to the new normal, the next wave hit: economic instability. For tech companies, venture capital funding dried up, marking the end to the growth-at-all-costs era. Suddenly every department had to justify its ROI in hard numbers. And across industries, tariffs, trade wars and supply chain disruptions shook the very foundation of how companies ran.

In November, 2022 OpenAI launched ChatGPT, thrusting AI into the public conversation on a grand scale. Overnight, executives started asking how AI could make their companies more efficient. What they were really saying was, how can we do the same amount of work with fewer people? Entire departments disappeared, merged or transformed into something new. Some companies over-committed and had to hire people back. But the expectation was clear - figure out how to use AI to make your teams more productive, or we’ll find someone else that will.

Each disruption on its own would have been manageable. But they didn’t come one at a time. They stacked. And each one reinforced the same message: the old rules are done.

• Performance doesn’t protect you.

• Experience doesn’t protect you.

• Expertise in something who’s future is unknown doesn’t protect you.

Leaders responded the only way they knew how: work harder, present a new plan, adjust to ever-changing expectations. But the old playbook was built for a stable game. And the game is no longer stable.

The real new normal (2024-now)

Here’s what makes The Corporate Reckoning so disorienting: it’s not a single event you can survive and move past. It’s a permanent restructuring of how careers, leadership, and corporate value are measured — and it’s still accelerating. COVID broke the workplace. AI is rewriting which roles exist. The economy is volatile. And none of these disruptions are resolving. They’re compounding on top of each other, each one making the next one harder to weather.

Being a talented executive with a proven track record used to guarantee you a long career. You’d do a good job, get promoted, build an empire, get hired away for a bigger paycheque and repeat this cycle until you retired to live out your days on a golf course in Florida. If you ever were let go, it was a temporary glitch and you were right back at it in 6 months. That world is gone. If the last 5 years has taught us anything, it’s that performance doesn’t matter like it used to. You can have the best strategy in the world, it’s not enough. A proven track record, everyone has one of those. Great leaders are being let go every day for one simple reason. The people hiring them don’t know what they want.

Executives think they know what they need today, but they have no idea what they’ll need in a year or two. Things are changing too fast. They’re guessing. All they really know is they want something different. If you’re different, they’ll hire you. But you’ll be let go in 18 months when they decide you weren’t the right kind of different. So, they’ll go find someone else different. In fact, that’s exactly what you see - leaders caught in a vicious cycle of changing jobs every 2 years. They spend more time looking for a job than they do in jobs.

It’s time to change the game

The leaders caught in The Corporate Reckoning aren’t failing. They’re doing exactly what the old rules told them to do: hit your targets, command the room, project confidence, stick to the plan. But every day they spend doing those things is another day they fall further behind a world that has permanently changed the criteria for who stays and who goes.

But there is hope - a lot of it. Now that we have a name for what’s happening, we can top flailing. We have a choice. We can stick to what’s always worked and hope the good ole days return. Or we can decide we’re not playing this game anymore, and start a new one where we make the rules. We can get proactive about what we do better than anyone else, so we can tell the world what it needs from us - instead of reacting to people that are guessing and changing their minds every two years.

In case you haven’t guessed, I don’t have this entirely figured out. For now, I take comfort in finally being able to explain what I’m seeing so I can have more conversations about it. Of course, it’s possible I’ve dreamed all of this up to distract from the reality that I really did become irrelevant overnight.

But I’m not giving up without a fight.

Music was my ticket

I was a lonely kid, with not a ton of friends. I remember my dad putting on his Led Zeppelin II record and slipping the headphones over my ears for the first time. Jimmy Page’s driving riff on, “What Is and What Should Never Be”, raced through my brain from one ear to another. Dunna, dunna……dunna, dunna….dunnanna. Back and forth. I must have listened to that album 100 times. I went to school the next day and talked to some kids in my class - the ones in the faded jean jackets with AC/DC and Iron Maiden written on them in black marker. We bonded. It was then I realized music was my ticket into groups that would never have me before. I slipped in an out of different musical genres over the next 15 years, and my friends changed with it. Music is how I found a sense of belonging. It made me feel less alone.

I didn’t realize it then, but that was my first introduction to the music time machine. If someone puts on that album today, I am immediately thrown back to the 70s shag carpet in our rec room, the one soaked with last night’s Labatt Blue and Du Maurier Lights. But a lot has changed since then. Before we get back to the future, let’s talk about how the time machine works.

The ingredients of the time machine

This is not a highly scientific study, but I’ve thought a lot about this. There are 3 key ingredients for the time machine to work.

1. Music gets imbedded.

2. Time happens.

3. Time machine is activated.

Music gets imbedded

When I was listening to that Zeppelin album over and over, it was burrowing it’s way into my brain. It was creating connections with everything in my life at that time - the sights, smells and emotions of my youth. That’s the only record of my dad’s I remember listening to. Once I got a part-time job, I started buying them of my own. I was making $2.85 at KFC and on payday, I would walk to the bank to cash my cheque, then directly to one of the 7 local record stores in the small town where I lived. I’d walk my new records home, close the door to my room and listen to every one. I’d pour over the liner notes until I knew every lyric to every song, even the ones I didn’t like. Because it was vinyl - there was no way to skip songs. And the artists agonized over the order of songs, that was part of the experience. So you learned the deep cuts on tracks 6, 7 and 8 that no one else would hear.

Time happens

Now that the songs are imbedded, you just need time. A time machine doesn’t really work without it. I’m convinced that if I had listened to Led Zeppelin consistently from the time I was 15 to now, the time machine wouldn’t work. My brain would be constantly overwriting my teenage memories with ones from my 20s, 30s, etc. It’s only because I took a break from Led Zeppelin for a couple decades that the time machine can throw me back.

But Led Zeppelin is a big deal, you really can’t go too long without hearing them. You hear their big hits on the radio or on Spotify playlists whether you want or not. So the time machine also doesn’t work for big hits. They can still remind you of earlier days, but they don’t throw you back in time like the deep cuts you haven’t heard since you first fell in love with them. The longer you go without hearing the music, the better the time machine works.

Time machine is activated

Later in high school, I got into The Smiths, Depeche Mode and New Order. It’s all I listened to for 2-3 years. But when I went to university, I wanted to reinvent myself so I left that music behind. About 5 years ago, I went back and listened to The Smiths for the first time in decades and I was almost in tears as the rush of teenage anxiety flooded back.

That’s the final ingredient of the time machine. It’s activated when songs you cared deeply about resurface after years of listening to other stuff.

How we broke the time machine

As I watch my kids listen to music, I realize they’re not going to get to experience the time machine like I do. I try not to fall into the trap of talking about the good ole days, and how much better everything was. But it makes me sad to think they won’t have music to bring them back to the smells and tastes of their youth. Once it’s gone, it’s gone.

I recently spoke to Alan Cross on my podcast. Alan is a legendary music historian who’s been hosting The Going History of New Music for over 30 years. It’s pretty intimidating interviewing one of your heroes, but the hardest part is figuring out how to compress a lifetime of musical questions into a single hour. Sure, we touched on his iconic interviews with David Bowie, Courtney Love and Ringo Starr. But what I was most interested in was how streaming has changed our relationship with music. Just how broken was the time machine?

Listen to my convo with Alan Cross

There is no going back, or is there?

Now that music comes out of the faucet for free, we don’t value it anymore. The average person spends a total of $80 per year on music. I spent more when I was 15 than I do now, and I’m a huge music fan. We don’t invest in a whole album, so there is no reason to stick with songs we don’t like. We quickly skip stuff that doesn’t immediately appeal to us. And the algorithm serves us more of what it thinks we will like to keep us listening. Anything disruptive or new runs the risk of waking us up. Maybe we get disinterested, close the app and go do something else.

My kids are big music fans, they listen to a lot of it. There is something about listening to my kids sing songs I didn’t teach them that makes me feel like a good parent. I introduced them to a lifelong musical companion, like my dad did for me, and his dad did for him. I just don’t know if those songs are going to resonate with them in the same way in 20 years. Will they have a less diverse palette to work from, because it’s so hard to discover anything new? Will the algorithm let them take a break from those songs so the time machine can do its thing? Will music lose its ability to transport them?

I hate to rely on technology to fix this, since it’s the thing that got us into this mess in the first place. But then I’m reminded that disruption is always a surprise. By definition, we never see it coming. When illegal file sharing services like Napster came along in the early 90s, it was a huge pain in the ass for the music industry. But no one could have predicted it would kill vinyl and CDs and eventually give rise to music streaming. That single moment changed everything.

So who knows what the next evolution of music will be. But rest assured, there is one coming. There is always another one coming. Maybe the next time machine is even better. I hope I’m here to see it.

And if you say to me tomorrow
Oh, what fun it all would be
Then what's to stop us, pretty baby
but what is and what should never be.

Now you might be thinking, “What does this have to do with me? I’m not on LinkedIn, or just barely.” Fair enough. LinkedIn is my drug of choice, but I bet you have one too. Instagram, TikTok, Twitter, Substack - or a colourful cocktail of these. Maybe your self-worth isn’t jumbled up with the online version of you, like mine is. But these platforms are insidious. They have burrowed their way into our daily lives. We can’t possibly see the effects until we step away. I had no idea any of this was happening. But now that I do, I can’t unsee it. And I can’t go back to the way things were.

So hear me out. I bet my story sounds more familiar than you want to admit.

LinkedIn and me

I started on LinkedIn in earnest about 6 years ago. My coaching and consulting business was doing fine, the way most solopreneur’s businesses do fine in the early days. But I’ve worked with enough founders to know that the word of mouth that pays the bills early on doesn’t last. You’re not a real business until you’re selling to strangers on the internet. LinkedIn is where my customers are, so it’s where I need to be.

LinkedIn is a strange place. It likes to pretend it’s not social media, but it is. It’s dressed up as a business networking site, but how many people see your content, and therefore how many customers you’ll find, is entirely controlled by an algorithm. You can say you don’t care, that you’ll write whatever you want. You’re lying. If you want to write and have no one see it, that’s what a journal is for. It’s ok to admit you want people to see what you do - why else would you be there? That goes for all social media. And every platform has their own weird rules to follow to get the eyeballs you want. What you share, how you format it, when you post - it all shapes how this online version of you evolves.

The birth of online Bob

Let me be perfectly clear, I’ve never said anything I didn’t believe on LinkedIn. But I believe a lot of things. On social media, you learn that sharing one thing gets likes and comments, while sharing something else doesn’t. It slowly starts to shape what you choose to share, even the positions you take. And it incentivizes you to stay in your lane. I’ve stopped posting about my podcast on LinkedIn, the thing I love doing more than anything else. When I used to post clips, nobody saw it. These are topics and conversations that mean a lot to me, and I’m proud of them. It feels like a betrayal to pour my heart out and get nothing in return - no likes, no comments. I don’t like rejection, so I stopped.

And the algorithm loves controversy. Anything that gets people wound up is going to get more eyeballs. An online version of you starts to emerge as you’re slowly conditioned to take bolder stances on a narrow range of topics. Every time you paint outside the lines, you’re met with silence. And you’re slowly nudged back. Your online persona gradually and imperceptibly bends to the will of the algorithm.

It’s not fake exactly, it’s you. It’s just not all of you. And the more time you invest in this online version of you, the more it gets confused with the real you.

My LinkedIn enema

I didn’t come to this realization right away, I was too close to it. They say a digital detox takes 72 hours. That’s how long it takes for your brain to recalibrate and remember how to live without technology. If you’ve ever done it, you know how disorienting it is. You feel naked. The daily pressure to show up on LinkedIn meant that I had started to “think LinkedIn”, like it was a language. Everything that happened during the day was a potential post. I didn’t absorb anything as I moved through life, as much as I was translating it into catchy LinkedIn hooks and posts in real time. Oh, this would be a good post. Or, I don’t need to pay attention to that - nobody on LinkedIn would care. It’s a shitty way to walk through the world.

The first few days felt like freedom. I no longer felt the need to write every day, even when I didn’t have anything to say. But more than anything, I realized how little I cared about what I was writing. Again, I wasn’t being disingenuous or saying anything I didn’t believe. I just didn’t care anymore.

If you ask anyone on LinkedIn what makes me different, you’ll hear things like authentic and vulnerable. When people meet me for the first time, they often say I’m exactly who they thought I’d be. I take a lot of pride in that. But the online version of me started to feel like a skin I had outgrown. And for the first time, I felt like a fraud.

My Substack playground

I joined Substack a few months ago to play. For me, it has no purpose like LinkedIn does. It’s where I write whatever I want. Writing is how I make sense of the world and my place in it. So, Substack is where I share those ideas, things I’ve learned not to talk about on LinkedIn.

But I’m a nobody on Substack. I have 400 followers compared to 13,000 on LinkedIn. I like the anonymity. I get to reinvent myself. But it also means nobody sees me. I write about deeply personal things, and I’ll get 1 or 2 likes. I’m not used to that. Sure I write about bullshit on LinkedIn, but I get lots of people responding and liking it. And that validation feels good. Our human need for acceptance and belonging is what the makers of social media platforms count on - to keep us engaged and coming back. That’s what the ‘Like’ button is for.

As you can see, I have a dilemma. I can write about shit I don’t care about, and have people tell me how great I am. Or, I can write about things that I care most in the world about, and have nobody care.

The reckoning

I was at an industry event a couple of months ago and somebody came up to me. “Hey, I know you from LinkedIn.” It’s as close as I’ll ever get to being a rockstar. It was a bit weird, but also kind of cool. I’ve thought a lot about that moment as I reassess my relationship with LinkedIn. I’ve often said that if I could run my business without it, I’d disappear and nobody would ever hear from me again. It’s kind of a badass thing to say. But it’s not that simple.

I’m a big deal on LinkedIn. I like being a big deal. I can’t pretend that’s not part of it. I hate that it is, but it is. But I’m known for something on LinkedIn that no longer fuels me like it used to. That’s why I can’t bring myself to write about the stuff I used to write about. I don’t know if what fuels me now is something anyone will care about. So I’m at a crossroads, in between this room filled with people that listen to what I say and an empty space where nobody knows my name. It feels safer to stay where I am. But I just can’t. I don’t belong there anymore.

It reminds me of what Bono said when inducting Bruce Springsteen into the Rock and Roll Hall of Fame.

I’ve been looking for a way to use that quote for years. So cool.

LinkedIn, it’s not you - it’s me

It’s easy to blame my identity confusion on LinkedIn. But I allowed this to happen. The truth is I’ve always been a bit of a chameleon. I think we all are, especially when we’re young and trying to find our people. There was Work Bob, Friend Bob, Dad Bob and Husband Bob. And there was always Party Bob, everyone’s favorite. I would surface different parts of my personality based on what people around me wanted to see. Maybe this makes me especially vulnerable to algorithms that feed on our constant need for validation. But as I get older, these different Bob’s are collapsing into a single one. Maybe it’s maturity, maybe it’s just laziness. Maintaining all these walls is exhausting. It’s definitely a young man’s game.

As I prepare for my re-introduction to LinkedIn, I’m very conscious of all of this. I know if I’m not careful, I’ll end up right back where I started. So a few things are going to change.

First, I’m going to start writing about what I’m really seeing in tech, where most people know me. This is going to ruffle some feathers. I’m not looking to be adversarial because the algorithm likes it, there are simply things I believe that nobody else is saying. That should be interesting.

I’m also painting outside the lines. There are things I care about that I’ve only shared on Substack until now. But I don’t have the energy to write in two places. So I’ll write what I want on Substack like I always have, and I’ll share it on LinkedIn too. And my podcast is coming back to LinkedIn. It’s fucking awesome, and if people on LinkedIn don’t care, they can scroll on. Or they can unfollow me and fuck right off.

Now, back to you

If you’re reading this and thinking, “man, Bob is really messed up”, I don’t blame you. That’s exactly what I would have said before I took my break. But if you’re a creator on LinkedIn or any other platform, this is happening to you too. I guarantee it. Maybe you’re not headed for an existential identity crisis like me, but you owe it to yourself to take a break and see what you learn.

Or maybe you’re not a creator - 95% of people on social media aren’t. Maybe you post pics of your kids on the first day of school, and your favorite Cobb salad. You’re still not immune. You’re still going through the mental gymnastics of deciding what to share, feeling good when you get likes and feeling dejected when you don’t.

Who knows - you just might find the online version of you has strayed a little off course too.

This is not easy to write about. It feels like something I should be talking to my friends about directly, before sharing it with strangers on the internet. I’ve been here before, and it’s definitely caused a reaction. That’s not my intent. But writing is my way of working through things that are bothering me. And this has been bothering me for a while. If nothing else, it helps me come to terms with what I’m feeling and what to do next. And I’m willing to bet, this is going to sound familiar.

The boys in the hood

I don’t have what you’d call lifelong friends. I have no friends from childhood or even high school. I do have a couple good ones from university. But most of the best friends I have today I met in my late twenties, when we all just happened to move into the same neighbourhood together. I didn’t know any of them before that. We were all the same age, had just gotten married and were starting our families. There were lots of dinner parties and road hockey games in the hood on Sunday afternoons. We became dads together, and our kids grew up together. They're not kids anymore. They’re in the twenties now, almost as old as we all were when we met. They already have the lifelong friends I never had. Whatever version of men us dads are today, we became together.

This neighbourhood has been our playground. I often say that second only to marrying my wife, buying our house in this neighbourhood is the best decision I’ve ever made. It’s shaped our lives and given my kids a childhood most parents only dream of. And my friends and I, we’re all still here.

Friends that just happen

These friendships were always easy. When you’re a new dad, there are two things that matter in the new friend department. The wives need to get along, and the kids need to get along. If those two things are true, we can be friends. We don’t even have to like each other, we’ll figure it out. But if even one of those critical pieces is missing, it’s probably not going to work out. It’s just too much work. You could be the best guy in the world, and we could have a ton in common, but if my wife doesn’t like drinking wine with your wife, we’re not going to be able to navigate around it. And if your kid doesn’t play mini-sticks or watch Pixar movies, it’s over before its begun.

I used to see my friends every weekend, like clockwork. It just happened. The wives would plan some kind of gathering and the dads would tag along. If that didn’t happen, there was always a Leafs or Jays game we’d use as an excuse to get together ourselves. On the rare occasion we didn’t see each other by Sunday, we’d always find a reason for a beer before the weekend was over. The idea of going back to work on Monday without a dose of friend time was unheard of. It happened by accident, or with almost zero effort.

Who knew kids were so important

Today, that’s all changed. I now realize kids were always the glue. Now that the glue has gone off to college, the dads are left on our own to hold these friendships together. We don’t see each other by accident anymore. We’ve gone from seeing each other twice a weekend, to going a month or longer before crossing paths. The wives don’t seem to have this problem. They still get together just as often as they always did, but they do it without the kids. And dads.

For the first time, it feels like the men are left to figure this out on their own. That rarely goes well. This is definitely new territory for me. I don’t ever remember my male friendships requiring work. They just happened or they didn’t. If it ever felt like work, they probably just died. I never thought much about it.

So far, I’ve come up with two potential solutions to this. I bounce back and forth depending on what mood I’m in.

Are we married?

Maybe I should think of my male friendships like a marriage, as in - they’re supposed to be work. Maybe they’ve never felt like work before, but that’s not reality. Not anymore. When my wife and I are feeling disconnected or haven’t seen each other in a while, we know we need to do something about it. We’ll have a date night, or a weekend away. We understand it’s not going to fix itself, and it’s too important to neglect.

For my friends, that means putting on my big boy pants, and making a call. Go for a coffee, watch a game together. Stop wallowing, and put in some work.

Or are we family?

Or maybe these friendships are more like family. My sister and I can go months without talking, but I know she’s always there. Maybe it’s ok that my friends and I aren’t as close as we used to be. It’s the natural ebb and flow of life. It doesn’t mean we’ll never be close again. Or maybe it does. Either way is ok. We’re like brothers. We love each other and we always will. And we know that if we ever need each other, we’ll always be there.

In other words, I could do what I’ve always done. Nothing.

Turning the page

For a long time, I felt responsible for all this. I quit drinking four years ago, and in doing so, I broke the social contract. There were no negotiations. I didn’t ask anyone’s permission. I changed the rules that governed how things always worked. It was just understood that we’d get together every weekend, have drinks, and talk about everything and nothing at all. And we’d do it again next week.

I now realize that part of our lives was coming to an end. Maybe the kids were the glue, maybe drinking was. And with those two pieces gone, things felt broken for a while. I know it was a little weird for them too, maybe it still is. But I can see it now - the Lego blocks of our lives reassembling to create something new, something stronger. Sure, we don’t talk as often. But when we do it feels more authentic somehow, like we’re letting each other see a little deeper. Our friendships can now withstand weeks without seeing or talking to each other. Even if I still miss them in between.

A new beginning

I wrote this post over three days and finally finished it on a Friday morning. But this isn’t the original ending. On that Friday afternoon, I had coffee with one of my close friends I hadn’t seen in about six weeks. If this article was written to any one person, it’s him. We had rescheduled our coffee date a few times, and I almost moved it again. It was a close call.

He came by the house and picked me up. What a strange feeling to be nervous to see one of your best friends in the world. I was wondering what we would talk about, if it would be awkward. And I wondered whether we would talk about the elephant in the room - that we just weren’t as close as we used to be.

As I sat down beside him, all of that unease evaporated. It was like no time had passed at all. It was as comfortable and natural as it always was. We talked about things I don’t think we ever would have talked about over drinks on a Friday. Those conversations were always easy and fun, and I don’t regret a single one. But it turns out, having the same conversation over and over for twenty years doesn’t tend to reveal much about anything that matters.

As I walked home, I felt like my cup had been filled. Left to my own devices, I’m inclined to sit home and withdraw. It’s my default state. But these people are a part of me. Along with my wife, my kids and my neighborhood, I don’t know who I’d be without them.

They’re not family and we’re not married. This is something new. It feels like there is absolutely nothing we can’t do.

We just can’t do it alone.

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The joy of the unknown

I started my podcast a couple of years ago. I was recently sober and looking for something to expand my horizons. All of a sudden, I had 7 days to play with instead of 4, and I wanted to do more. I didn’t know what I wanted to do more of, but having interesting conversations with interesting people seemed to be a good place to start. So that was the only rule - talk to people I had never heard of, doing things I knew nothing about. It was a purely selfish pursuit of my own curiosity.

I started having amazing conversations with adventure-seekers, creators and authors. If you were doing something cool I knew nothing about, you fit the bill. I was loving it. But then I started thinking, “So what’s in it for my audience?”, and “How can I be helpful?” Those seemed like logical questions - after all, I do want people to listen. And if they’re going to listen, there has to be something in it for them. Right?

Well, sort of. I started trying to be more helpful by talking to people about things I’ve always struggled with - confidence, imposter syndrome and finding my purpose. There is not a day that goes by I’m not working through some combination of these issues. I was still learning a lot, but I noticed something else. The podcast was starting to lose its emotional charge. It was starting to feel like a job - a job I didn’t love anymore.

The wake-up call

One morning, something came across my Instagram feed. It was a new book called, The Gales of November - The Untold Story of the Edmund Fitzgerald. The Mighty Fitz, as the ship was known, was a 730 foot iron ore freighter that sank in the storm of the century in Lake Superior 50 years ago. All 29 men on board were lost. It sank without warning - one minute she was there, the next she was gone. Gordon Lightfoot wrote a song about it in 1976 that is still the definite song of nautical disaster, and if you know the name Edmund Fitzgerald at all, that’s probably why. It was the #2 song in the world, right behind Rod Stewart’s, “Tonight’s the Night.”

Like so many others, the story of the Edmund Fitzgerald played a big role in my life. I love Gordon Lightfoot, and my dad and I used to talk about the mystery as we were bobbing around in Lake Huron fishing for lake trout and salmon. When that book came across my feed, I jumped into action like a ten year old on Christmas morning. I had to have the author on.

I reached out to John U. Bacon and basically begged him to be on the podcast. He agreed, and we set a date. I can’t remember the last time I was that excited. I poured over the book and by the end, I had folded the corners of 44 pages - each one marking something I was dying to ask John about. It wasn’t easy, but I widdled it down to an hour’s worth of questions. John was amazing, and we had what I think might be the most interesting conversation I’ve had in almost 60 episodes. But here’s the thing - unless you are a Great Lakes shipping captain, there is absolutely nothing helpful about it.

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The problem with self-help

I’m been binging on a lot of self-help books and podcasts lately, and it was clearly seeping into my podcast. It’s what I was genuinely curious about for a long time, and I thought if it was helpful to me, surely it would be helpful to others. But I’ve become exhausted by it all. Do these 5 things to improve your marriage, do these 3 things to find your purpose. Tim Ferris talks on a recent episode about how every self help book is a variation on the same thing. So do yourself a favour and pick one book, any book. And do what it says.

But we don’t. We read it. We love it. We tell our friends. We make a couple small changes. We feel great about ourselves. Then we stop. And we pick up the next book, and what do you know - it sounds like it was written just for us. This is exactly what I need! And the cycle continues.

The biggest problem with self-help is that its self-fulfilling. It requires that we’re always looking for new things in our lives that need improving.

There is no way out.

Back to curiosity

Do I struggle with confidence and finding my purpose? Hell yeah, every day. But I can’t keep talking about it unless I’m willing to do something about it. I have everything I need. I’ll toil away on it, but I don’t need to drag everyone through it with me. Besides, the listeners of my pod, they know the answers too. So maybe the best thing to do is go back to chasing my curiosity, and let that be the inspiration people need.

So that’s what I’m doing, and so far it feels great. My first interview after the Edmund Fitzergald episode was with Alan Cross. Alan is a legendary music icon and host of a show called, “The Ongoing History of New Music”. I've been listening to Alan on the radio, and now on podcasts, my entire adult life. I was shocked and a little terrified when he responded to my email and said he'd come on. I was overwhelmed thinking about what people wanted to hear. All my friends are music fans, they love Alan Cross. What do they wish they could ask him? Are they going to listen to this and be disappointed because I wasted this once in a lifetime opportunity? It was paralyzing.

Then I stopped and simply asked myself, what would I ask Alan if I had him alone and nobody but the two of us would ever hear this conversation? What am I most curious about?

So that’s what I did. And it was incredible. We talked about the changing role of music in our culture and how the economics of the music industry is changing what artists make. Music has always been a big part of my life, part of my identity. And it's become a big part of my relationship with my kids. I don't even know who I'd be without it. But it's changing, and I want to understand that better - for me, my kids and my kids' kids. I asked completely different questions to Alan that anyone else would. Because it's what I care about. It's not meant to be helpful. It's meant to be interesting. Whatever people take away beyond that is up to them.

Curiosity as inspiration

I admit this pivot felt like failure at first. It felt like I was giving up on my pursuit of helping people, of being of service. It felt selfish. But I don’t see it that way. I’m simply leading with my curiosity. Yes, its bound to lead me down some rabbit holes that don’t go anywhere. Some of the places I end up will be awesome, some won’t. Some will feel right for a while, then lose their emotional charge. And that’s how I’ll know it’s time to turn around again.

It seems like a revelation to try to provide people a distraction from their normal lives, to step outside themselves to listen to interesting stories without bashing them over the head with lessons and next steps. In a world where everything feels like it needs to have a point, an outcome - let’s just fuck around and find out. Let’s get lost. Maybe that’s what we all need more than anything.

And here’s the truth about inspiration - its everywhere if you’re in the mood. You can listen to the story of the Edmund Fitzgerald and simply take in the greatest story of nautical disaster ever told. Or can listen more carefully and hear about courage, brotherhood, heartbreak and the power of mother nature. And maybe you listen, reflect and go home and hug your kids a little tighter tonight. It’s up to you.

I hope this has been helpful. With any luck, you've heard something that sounds familiar as you plan something you always wanted to do, or try to rediscover the joy of something that’s lost its spark.

Either way, I hope you were entertained.

Let’s use music as the most obvious example. By shining a light on the ugly truths of streaming, we see how it’s changed our relationship with music and is subtly stealing our creative freedom.

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The economics of streaming

On Spotify or Apple Music, 35% of songs are skipped before the 30 second mark. Maybe that’s not surprising in this age of shrinking attention spans. Basically, if you don’t recognize the song, you skip it. Or if it’s new and you don’t love it right away, you skip it. When Spotify tries to sneak a Steve Miller song into my Tom Petty radio, you’ll see exactly how fast this can happen.

But it turns out this is really bad news for artists. They only get paid if the listener listens for at least 30 seconds. So if you’re skipping a song from your favorite artist at 25 secs, they don’t get paid. Play it for 35 secs, and they do. Of course, they don’t get paid much - between $0.003 - $0.005 per stream, but it’s something.

While the Bruce Springsteen’s and T Swift’s of the world still make plenty, the picture is far less rosy for others. This is especially true for artists trying to break into the music biz. But that’s not even the worst part. Because this economic model is changing how people write songs. It’s changing the art of music.

If you only get paid when people stick around for 30 seconds, you don’t have time for long intro’s. You don’t have time for nuance. You need to hook people with sugary riffs and catchy lyrics right away. As more and more artists try to make a living in this new world, all our music starts to sound the same.

The end of the classics

Stairway to Heaven is one of the most popular and influential songs ever written. You don’t have to be a Led Zeppelin fan to recognize the impact that song had on music, and the hundreds of other artists and songs it inspired. It was so different than anything people had heard at the time.

But would Stairway be written today? If it was, would anyone hear it? “There’s a lady who’s sure…” doesn’t show up until 0:53. Do you think new listeners would have made it through the quiet guitar and flute before skipping on to something more familiar? Would Plant and Page have been tempted to shorten the intro? Would Stairway be the same? What about every song that came after it?

What about Hotel California? Coincidentally, it also takes Don Henley 0:53 to get to “On a dark desert highway…”. Can you imagine the song without Glen Frey’s beautiful guitar intro, with every note in exactly the right place?

Phil Collins doesn’t start singing, “I can feel it coming in the air tonight” until 0:51. Is a world without that iconic drum solo one we even want to live in?

I could spend an afternoon doing this, but the point is that technology is changing the art we make. It begs the question how many future iconic songs will never be heard, or never be made, because of how we listen today. For music fans everywhere, that’s a soul-crushing question. It’s slowly rounding the sharp corners that make artists unique, so that everything sounds the same.

And it’s not just happening in music.

From listening to creating

I spend a lot of time on LinkedIn. It’s where my customers hang out, so it’s where I hang out. Until launching this Substack, it was the only place I shared my ideas. It has been great for me. I’ve found the courage to talk about very personal things and painful experiences even some of my best friends don’t know about me. But just like Spotify is changing what we hear, LinkedIn is changing what I say.

I don’t care what anyone says, you can’t say what you want on LinkedIn - or any other social media for that matter. Or at least, you can’t say it the way you want to say it. If you want people to hear you, you have to play by the algorithm’s rules. That means catchy titles and weird formatting because that’s what drives impressions. Stick to your artistic principles if you insist, but you’ll end up writing to yourself. That might be ok for your gratitude journal, but you’re sharing your work for a reason. And whether it’s building a brand, finding leads or creating a network, nothing works if you shout into a void.

The same is true for whatever your social media platform of choice is. Where you express your ideas has its own rules, and those rules change what you create.

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Stay aware and take care

For me, I’ve decided I need more places to share my ideas so I’m not at the whim of a single set of rules. I’m hedging my bets. Yes, I will do my best to write without caring about the algorithms that ultimately decide if anyone sees it. But I know that’s not entirely realistic. I want people to see my stuff, and that will inevitably shape what I create. I don’t see any way around that. Maybe by sharing my work in different places, I can at least see what works where. Then I can decide which places allow me to be the most me.

Right now, Substack is that place. It’s where I start. Yes, it has an algorithm, but it’s where I’ve decided to write what I want to write, what pours out of me. Then I take those ideas and contort them for the LinkedIn algorithm. That might change, but that’s the experiment for now.

If you have something to share, find a place that allows you to express the purest version of what you have to offer the world. If that is social media, it’s bound to shape what you do over time. These algorithms are designed to work below our subconscious to change our behaviour. Shear willpower is not enough. Take breaks, share it in different places. Be mindful of how the medium might be changing what you do.

As Austin Kleon says, “We don’t write because we have something to say. We write to find something to say.”

Keep going. Keep putting yourself out there. The robots will do their thing.

Your people will find you.

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Our morning routines say a lot about us

Most of us have a routine to start the day. Some are elaborate and structured, some are gentle and easy. For me, I’ve always tried to batch up my non-negotiables so I could be sure they got done. Journaling, exercise, stretching, fresh air - these are the things I need to be at my best. Since morning feels like the only time of day I have complete control, I make sure they’re all done before I open my laptop. After that, anything can happen. This is how I operated for years.

Maybe you’re one of the world’s weirdos that doesn’t have a morning routine and still manages to live a happy and productive life. I’m jealous. I’ve been searching for the right routine for years. In the early days of my podcast, one of my opening questions was, “Tell me about your morning routine.” The idea was that if you were successful at something, you must have a morning routine I could borrow from. I’d hear the usual things, from journaling to exercising, until I talked to Sylvia Baffour. She’s an author and speaker on emotional intelligence, and was mentored by Maja Angelou for 20 years. She’s incredible. When I asked her, she said she wakes up whenever, has a coffee, and maybe goes for a walk. She lets her body tell her what she needs. So much for every successful person starting their day with a common set of rules. I stopped asking the question after that. While I love the romantic notion of starting my day like Sylvia’s, I’m not there yet.

Mine worked great, until it didn’t

I’ve had the same version of a morning routine for years now. When I deviate from it, I feel off. So I protect it. I stick to it. When I travel, I take everything I need.

1. Wake up at 5

2. Make coffee (5 mins)

3. Do morning pages (30 mins)

4. Stretch (25 mins)

5. Walk, run or bike (1.5 hrs)

6. Soak in the hot tub (20 mins)

7. Walk upstairs to my office (2 mins)

Believe me, I’m not one of those typical ‘up at 5am’ over-achievers. It’s just when I wake up. Maybe you’re a night owl, and get up at 11. All the same rules apply.

For a long time, my routine checked all the boxes. There was just one problem. I realized I was wasting the most creative part of my day doing non-creative things.

I am most creative from 5am - 10am. Ideas come easy. I solve problems by accident. But my morning routine eats up most of that time. By the time I sit down to work, it’s 9am and I only have an hour of good brain time left. If I’m doing mindless administrivia I can do in my sleep, that’s fine. But if I’m writing, crafting speeches or preparing for my podcast, I need those creative juices. I end up working long hours. I’m always busy. But I never make enough progress on my most important work.

Making the most of your creative time

About a year ago, I did a simple exercise that helped. I started paying attention to how my work aligned with my creative energy. It went like this:

1. I made note of when I felt most creative (early morning, mid-morning, midday, afternoon, evening).

2. I reviewed my calendar and bucketed each meeting (1- need creativity, 2 - can do without it).

3. I reviewed the work I did outside meetings, when I did it, and put it into the same two buckets.

4. I lined it all up.

The results were obvious. I was wasting brainpower. I was doing work in the morning I could do in my sleep, when my brain was at its best. And I was trying to be creative later in the day when my brain just wasn’t up for it. I’d get frustrated rewriting the same paragraph for an hour, or staring at a blank screen waiting for a great idea to come, only to have the solution show up in my morning pages the next day.

So I changed my work around. I blocked off time in my mornings for creative work, and I left all the easy stuff for after 3pm. It was a game changer. And it worked for a long time.

Tearing down your routine

The one thing I was never willing to mess with was my morning routine. Then I heard an episode of Tim Ferris’ podcast with author, Jim Collins (From Good to Great). Jim is a writer, so for him being creative isn’t a luxury, it’s his job. His most creative time is 5am - 10am, just like me. So, he wakes up every day, makes a coffee and writes. Everything else he needs to do happens later. I’ve often wondered how someone finds the time to write a book. It feels like at the rate I’m going, it would take me 10 years. Like running a marathon an inch an hour, two feet a day. I started wondering how much more I could get done if I harnessed every hour of my creative morning. I’d have 5 creative hours to work with instead of 1 or 2.

This is where it got uncomfortable. I rely on my routine for my mental health, especially exercise. The only way I can make sure my run or bike ride happens is by doing it in the morning, before the rest of the world gets a hold of me. And I love getting out in the morning. There is less traffic and fewer dogs. Sometimes, I can be out for an hour before sunrise, and never see a soul. I’m nervous about messing with something that’s worked for years.

Uncomfortable or not, something has to change if I want to get more done. So, I started dismantling my routine, and challenging assumptions I’ve been carrying around forever. What if I did run in the afternoon? Yeah, there are cars and dogs, but I can dodge those. Maybe it would even restart my creative juices so I’d have more creative time to work with. What if I blocked time in the afternoon to make sure it happened? Then, there’s stretching. If I’m not running in the morning, maybe I can do that later too. And how else could I get fresh air in the morning? Maybe I could do a short walk after my morning pages, before I sit down to create.

Putting the pieces back together

My new routine looks like this:

1. Wake up at 5

2. Make coffee (5 mins)

3. Do my morning pages (30 mins)

4. Walk (20 mins)

5. Create (3 hrs)

And I’ve added an afternoon routine:

1. Stretch (25 mins)

2. Run or bike (1.5 hrs)

3. Soak in the hot tub (20 mins)

4. Create again (?)

This is going to be an adjustment. It will have a dramatic impact on how I work, and when I’m available for different kinds of meetings. But the idea that I could get 3 extra hours every day is too good to pass up. It’s magic. What at first felt scary, now feels exhilarating.

And what did I do, really? I simply put some distance between me and my habits, and got curious about what else might be possible. It’s also made me wonder what other parts of my life are held together with habits I am blind to, because they’ve been there for so long. How much more time could I find? What other parts of my life could I experiment with?

What more could you do?

I realize real life can get in the way of your ideal routine. Maybe you have kids to get to school, or put to bed. Maybe you have a job with less freedom to work how and when you want. Even so, if you’re willing to think differently, I guarantee you have more options than you think. Reshuffle your non-negotiables. Ask yourself, ‘when are you at your best?’ What are you doing at those times? Are you wasting the best parts of you on tasks that don’t need it? Does it take you way too long to get important things done, because you’re trying to do them when you’ve got nothing left?

I’m slowly realizing the longer I’ve been doing something a certain way, the more it probably needs to change. I’ve always worn my dogged discipline like a badge of honor. Maybe it’s better to always be moving, to never get stuck.

To always be experimenting.

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The pandemic is not over

I had a friend tell me a year ago, “I’m tired of hearing about the Covid hangover. It’s bullshit, it’s just an excuse.” But, I see it every day in the faces of people I talk to. It explains a lot about how people in their 40s and 50s are feeling. The pandemic forced us into a collective midlife crisis, together. We were so eager to get back to normal, we were deaf to the unanswered questions it left us with.

It’s getting harder and harder to remember work before the pandemic. It’s like trying to explain what flying was like before 911. Arrive 20 minutes before your flight, leave your shoes on and bring all the nail clippers and shampoo you can carry. What a world. Before the pandemic, we went to work every day. Unless you had a sick kid at home, there was no virtual work. We made friends at the office, we met our future spouses there. We went out for drinks. We were connected. It wasn’t always easy, but we were all in it together.

When the pandemic was over and we started returning to “normal”, we couldn’t possibly know that world was gone forever. Things inched back slowly, and we expected it to keep going. But then it came to rest in this strange land of hybrid work, where our jobs changed without anyone asking us. We have a collective hangover we’ve now had for so long, we don’t notice it anymore. We have forgotten what sober feels like.

An uncomfortable pause

The pandemic shocked people out of their normal routines, just long enough for them to start asking questions they weren’t ready to answer. We never had time to question whether this is really the job we wanted - we were busy trying to keep up. I had someone describe it this week as, “an uncomfortable pause.” But then this pause ended. And now five years later, we’re just realizing this job doesn’t fit like it used to. Everyone is feeling off at the same time. Millions of podcasts have sprouted up, claiming to have the answers. Spoiler alert - they don’t have them. I know because I’ve listened - to all of them.

It’s important to note that most of us aren’t miserable. In fact, life seems pretty damn good. If you ask us, we’ll say, “yeah, everything is fine.” And we’re right. Everything is fine. But there is a growing restlessness. It’s stalking us, whispering to us, “something isn’t right.”

The AI accelerant

As we’re all struggling to find the comfort and confidence in our work we once had, AI has landed. We don’t know what to believe, but we know it’s going to change the jobs we’re good at today. We feel this pressure to learn it, to prove we’re keeping up. But we are so busy trying to stay relevant, we’ve never asked ourselves if this new job is one we’d even apply for. Can you adapt to this new version of your job? Sure, you can. People much dumber than you have done it. But, do you want to at this stage of your career? And are you doing it because you’re genuinely interested, or are you afraid it’s the only job you know?

Ten years is a lifetime

For me, I’m growing less interested in the work that’s paid the bills for the last ten years. I’ve outgrown it, or more likely it’s outgrown me. It’s for the best. I’ve got ten more good years left, and I refuse to spend another day doing work I don’t love. I think after a career of doing what everyone else wanted me to do, I’ve earned that.

So, this is a reminder, your permission slip. You don’t have to keep up. Listen to that voice that’s telling you this isn’t good enough. This is your chance to get curious about how to take all the incredible skills and experiences you’ve amassed, and point them to something that makes you jump out of bed in the morning. How long has it been since you felt that?

The funny thing about midlife crises, they rarely happen midway through life. My dad had his at 45, and he died at 48.

How many stories do we need to hear like that before we finally decide to do something different?

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I want to state clearly, that writing about this terrifies me. I don’t know how it will be received, what people will think of me and my views. But I haven’t seen enough people come to the defense of these players, I assume because they too are afraid of being judged. Maybe it’s because I am the father of two sons, about the same age as these players. When I imagine them in that room, what do I think they would have done? What do I wish they would have done? And how would I feel watching the world judge them? The short answer is, I don’t think they would have done anything differently. That doesn’t feel awesome. But I understand.

Let’s consider the context here, something the internet isn’t always great at. The guys on that team just played the greatest game of their lives. They’ve dreamed of this moment since they were boys. They are on top of the hockey world, hugging and screaming with joy. A tournament like this takes everything you’ve got, physically and mentally, and the feeling of winning - that release, is something few of us will ever experience. In the middle of the locker room celebration, someone yells, “Hey quiet, the president is on the phone.” The room goes quiet, and after the usual congratulations, DJT invites the boys to the White House for the State of the Nation in two days. He goes on to quip that he also has to invite the women, who also won gold for their country, or, “I do believe I probably will impeached.” It’s all caught on camera, and you can see the guys laugh.

Is this a disgusting joke, made at the expense of a group of incredible women who also proudly represented their country and won it all? 100%. Is it in poor taste, disrespectful, and everything we don’t want our leaders to be? Yeah, and what about that surprises you? Frankly, this is about the nicest thing I’ve ever heard this president say about a group of women. It could have been so much worse.

But what do we expect this group of men to do in this situation? Are we really suggesting that in the chaos of the moment, we expect one of them to speak up and say, “I’m sorry Mr. President, that is in very poor taste and we are proud of the women’s team?” C’mon. By all accounts, these players are huge supporters of the women’s game. And contrary to popular belief, most pro hockey players are very good, kind people, from great families. They cherish their mothers, sisters and daughters. They are dedicated family men.

Do I think there are players that didn’t think twice about the joke in the moment? Yes, it all happened so fast. Do I think there are players that were uncomfortable with it? Yes. Most importantly, do I think that some of the guys have thought about it since, regret it and wish they had done something different? Of course. And both things can be true. We can be disappointed that everyone went along with it. And we can have some grace, and recognize that 99% of us would have done the same thing.

I was born in 1970, not that that excuses anything. But I have told racist jokes, and laughed at even more of them. I have told jokes that put down women, I have tried greasy pickup lines, and I have treated people poorly. Would I tell those same jokes today? Of course not, I am a different person. Do I hope my boys never tell jokes like that? Yes, without a doubt. But I also recognize that we all deserve the chance to make mistakes and learn from them, without the world judging us on every decision we make in a chaotic moment, or every joke we laugh at. I would hate to think that people who heard a younger me tell those jokes would judge me so harshly as to never believe I can change.

P.S. I am an avid Canadian hockey fan, still recovering from a broken heart, after watching our boys lose to the US. If I can find some understanding in this, anyone can.

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A couple of years ago, I started feeling this sense of urgency to do something more with the last ten years of my career. Like anyone in their 50s, I’ve done a lot of stuff. None of it has been particularly intentional. I went to school, got a job, got promoted, got offered another job, and so on. On paper, it looks impressive. But as I sit here looking down the barrel at the end, I can’t help but wonder if this is really all there is. Shouldn’t all these experiences, mistakes and stories amount to something more? Don’t I have more to offer the world before I fade away, than a list of jobs and bullet points on a resume?

So I started trying new things, things that always scared me. I played open mic nights, I started speaking in front of larger audiences, and I started sharing my personal experiences on my podcast, on LinkedIn and on here. OK, I admit these are not ‘solo-climbing up a skyscraper’ level scary, but they are big deals to me.

Then something happened that gave me pause. It was a corporate speaking gig. Now, I’ve done hundreds of these, but I was experimenting with some new things. It went off without a hitch, and I got great feedback. Good for me. But as I sat in my downtown hotel room after, it struck me how fleeing the sense of accomplishment was. I had spent hundreds of hours preparing, editing and rehearsing. I spent less than an hour delivering it, and even less than that feeling good about it. During the weeks leading up to the event, my speech was the first thing I thought about when I woke up, and the last thing I thought about before bed. It consumed my waking hours. Those are hours I should have been present with family and friends. And I simply wasn’t.

And for what? 45 minutes of adulation from strangers I’ll never see again? I didn’t even get the rush afterwards I so rightly deserved. I felt good about myself for a few minutes, then my mind was flooded with all the things I put off to get this thing done. I’m tired of chasing scary things, living outside my comfort zone. It’s exhausting.

I wrote an article a while back, called, I Miss My Friends. It was written out of frustration that my friends didn’t listen to my podcast, something that is deeply personal and important to me. If they loved me, wouldn’t they want to support me enough to listen for a few minutes every 2 weeks? Surely that’s not too much to ask. I came up with all kinds of stories in my head about why they didn’t. Of course, I could have just asked them, instead of airing my dirty laundry to strangers on Substack. Because when they heard about it and confronted me, I learned something that never occurred to me.

People get tired of hearing about living outside their comfort zones. “It’s intimidating.” It never occurred to me that there are lots of people, including many of my friends, that are perfectly content with their lives. They have jobs they’re good at, and like enough. They spend quality time with the people in their lives that mean the most to them. They’re active and healthy. Who am I to ram growth and comfort zones down their throats? The last thing I ever wanted to do was make people feel like there is something more they should be doing with their lives, just because I do. They’re perfectly content living inside their comfort zones. And frankly, I’m jealous.

Which, brings me back to finding a balance, something that’s never really been my thing. The pendulum is always way to the left or the right. I’m always stuck in my routines, squarely in my comfort zone, living day to day without much thought. Or, I’m chasing big, lofty things because I’m running out of time to do something more. It doesn’t mean I don’t want to keep growing. I do.

But we don’t have to be chasing growth every day. We deserve to slow down and enjoy all the things that used to scared us, but no longer do. Surely, that’s the point of stretching your comfort zone, savouring how far you’ve come once in a while.

So don’t believe what Instagram tells you - growth can happen squarely in the things that feel safe and familiar.

And I’ll see you there.

P.S. Believe it or not, this image was NOT made with AI (it would have gotten the math right).