I felt like I had finally “made it.”

Then one very meh spring day in early March in Boston, I saw two very distinct pink lines on an at-home pregnancy test.

(And to get ahead of this, no, having my son was not the grand finale to my grand downfall; however he is the reason I am amazed at the types of songs I will come up with to get him to focus for one single iota of a second.)

In one swift kick to the metaphorical ass, my entire world went upside down, and the hilarity of it all is that in the midst of one of the biggest changes of my life, I had the delusional audacity to think that nothing about me would change either.

(Dumb. So very very very dumb.)

In my naive, fully developed brain, I thought I would rally through this pregnancy, pop the offspring out, get he/she into a good daycare at four months old when maternity leave ended, and la-ti-da my ass back to my hard-earned big girl career - because that is what every single career-driven woman ahead of me had done for the last twenty years, and I was a GIRL BOSS and that is what GIRL BOSSES DO.

Flash forward almost fifty-six arduous, vomit-filled pregnancy weeks, one c-section, and intensely sleep-deprived months later, I found myself sitting and staring at my laptop the night before I had to return to work, wondering who the fuck was supposed to show up tomorrow and act like everything was the same - when literally everything about me was, in fact, not the same.

I had no idea who I was or what I was doing with my life. For the last four months, my entire identity had been obliterated, and my brain only rotated around nap schedules, breastfeeding, passing out on the actual nursery floor when he wouldn’t sleep, wanting to throat punch my husband (who I do love dearly) and also cry at the same time, all while realizing my old life was effectively cooked - done and dusted - and nothing I could do would ever bring it back.

I was the happiest and saddest I had ever been.

Yet here I found myself staring at this laptop, re-downloading Slack to catch up on mindless company chatter. I couldn’t understand how women showed up after barely surviving four months of postpartum and were just expected to “get right back in the saddle,” when all my brain was screaming was “FUCK THIS SADDLE.”

And before we chalk this whole mentality up to being a NeW mOm or - God forbid - hoRmOnes or BeInG OvErWhelMed, there are countless, and I mean countless, studies that show the literal brain chemistry of a woman after having a baby is simply not the same. So riddle me this: how could I have expected myself to “show up and be the same” when I biologically did not have the same wiring anymore?

No clue.

But I logged on the next day and smiled like a mental patient who just escaped an asylum, and I attempted the classic “fake it till you make it.” When my first day back ended, I immediately told my husband I, in fact, could not “fake it till I make it,” because my innate ability to bullshit myself no longer worked.

My old identity, who only cared about keeping a good poker face and not rocking the boat, did not stand a chance against my new, unknown identity.

This version of me absolutely did not give two shits if the boat capsized or blew up in my face. She was sleep-deprived and feral and probably hadn’t brushed her hair in days (okay, realistically weeks), and the more she tried to cling to this old life she’d worked so hard to build, but no longer fit into, the more her new life demanded she burn it down.

And when life finally got sick of me not catching the drift, it burned it down for me- and boy oh boy did it burn.

Within exactly sixty days of returning, and one afternoon Zoom call with HR and a new boss I could never successfully work for, I watched the career and role I worked so hard to get become redundant. It felt like my world was simultaneously crashing down and yet I was actually able to breathe for what felt like the first time in years.

(Looking back- holding those two diametrically opposed feelings was a mindfuck in the moment.)

The stable paycheck was gone.

The falsehood of safety within a corporate role was gone.

The veil of “enjoying the corporate grind” I could hide behind was gone.

It was all just gone.

And the most brutal realization of it all was that somewhere deep down, I knew I had asked for this exact universal “balancing of the scales” because I had felt so deeply disconnected from my own path for so long and incredibly lopsided in how I truly envisioned my work and purpose for my life.

(BUT I just was innocent enough to think that my own exit from this path would be on my own terms- once again- despite me being very smart, this was also very dumb dumb dumb).

I needed depth and meaning and a career by design, not a career by default.

It was almost as if life needed to make those final months so unbelievably brutal just to get my attention, so I would finally realize that this was it. Corporate was done, and all these years I had spent becoming a good and competent employee, while valuable, were no longer going to work in the next phase of my life.

You see, what I missed - or rather, failed to listen to - when I first saw those two pink lines all those months ago, was all the little universal signs and whispers that were telling me to let go.

Let go of your old life, because it’s going with or without you the minute you hear your baby’s first cry. (It’s worth it, I promise.)

Let go of twenty-one-year-old you, who was just a scared kid who needed to pay her bills, so she did what she “thought was right,” even though every new promotion felt like a betrayal to herself. (The skillset gained is and will always be invaluable.)

Let go of all the anger and resentment when the countless hours you put in went unnoticed - on projects, spreadsheets, other people’s work, all of it. (It won’t matter the first time your kid smiles at you.)

Let go of the constant, and I mean constant, pressure and fear that if you don’t girl boss hard enough, generate a six- or seven-figure income, drive a nice ass car, and live in a bougie apartment all before you’re thirty (Jesus, I was tough on me), you won’t have value. (Turns out your value is not a dollar amount.)

Let go of the judgment for staying in a role you thought was “temporary.” (That “temporary role” gave you so many incredible friends and opportunities.)

Let go of meticulously needing a plan outlined or a next step so clear and obvious it would be unreasonable or unfathomable for your plan to fail (Two things: your “plan” will fail and you need your “plan” to fail or you’ll miss one of the biggest and brightest growth pivots of your life).

Let go of who you think you are, so motherhood can show you who you have always been. (Welcome to the real you -she’s so incredibly free from her own bullshit, finally.)

Turns out the grand finale to my grand downfall was just a woman on her kid’s nursery floor at 3am, deciding she was done performing a life that was never actually hers to begin with.

No fireworks. No rock bottom montage. No theatrics.

Turns out I didn’t lose myself in that nursery. I just met her for the first time.

And if you’re standing where I was - staring at a laptop, mourning a version of yourself that isn’t coming back - I need you to hear this the way I couldn’t: you’re not disappearing. You’re finally, finally arriving.

Let go. Let go. Let go.

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Sitting outside of my precious, trendy co-working office- or rather former co-working office, jobless and sobbing..

I had never been laid off, never not been a top performer, never not had the next thing already lined up, and looking down at a measly two-week severance package was simply not helping the dollar signs stacking up in my head as I mentally tallied rent, the brand new puppy, the car payment, and every other expense I had taken on under the assumption that my paycheck would, you know, continue to exist.

So naturally, I called the very nice but very dead-end boyfriend at the time, and in between dramatic, theatrical, gasps of air, tried to explain what had occurred just twenty minutes ago -fully expecting either a matching level of dramatic outrage on my behalf, or a “don’t worry babe, we’ll figure this out,” or really just anything that resembled basic human comfort, and instead what I got was:

“Damn, that sucks. I’m gonna go back to bed. I’ll call you later.”

(He did not call me later. He “forgot.” Also, sir, it was the middle of a Tuesday afternoon, why on God’s green earth were you going back to bed????)

There was absolutely no chance in hell I was calling my family to inform them that I had- for the first time in my admittedly short adult life- failed at something. I did not need the unrealistic, sky-high expectations I had already set for myself reinforced and doubled down on by a barrage of probing, well-meaning but soul-crushing questions about What I Was Going To Do Next and How I Was Going To Pay My Bills and Did I Maybe Want To Move Home For A While.

So I just sat there. On the curb. Staring blankly at two homeless men in the alley fighting over what appeared to be a single, sad joint.

And instead of doing what any rational, emotionally regulated human being would do- which is take a deep breath and remind myself that I was, in fact, not the first person in the history of the universe to get laid off and there would absolutely be other opportunities- I instead pulled out my phone and Googled: “nearest blood plasma donation center” and “how much do you get for egg donation if your genes are good but not, like, great great.”

An hour passed. I was now several browser tabs deep into egg donation research, had just submitted a request for a consultation, and was actively calculating whether two rounds of donations could cover three months of rent, when my phone rang.

CALLER UNKNOWN.

(The fact that my very first thought was damn, that was fast, I must have desirable eggs and not this seems incredibly suspicious and I should absolutely not answer, I have no idea)

“Hello, Ms. Anderson. This is the IRS. You have not paid taxes in ten years and you are now going to be arrested for fraud unless you immediately send us twenty Visa gift cards in the amount back owed. The police are currently on their way and we know your exact location. Do not move. Do not hang up.”

If I had possessed even a single ounce of logic, rationality, or basic third-grade math skills in my brain at that very moment, I would have very quickly put together that a) this would mean I had stopped paying taxes at the ripe old age of thirteen (child labor laws???, b) the IRS does not, in fact, call you when they have an issue with you- they send you a very boring, very official letter in the mail, and c) this was very obviously a scam call from an overseas call center because I could literally hear the rhythmic clacking of fifteen other people in the background reading the exact same script to fifteen other unsuspecting victims.

But instead I started screaming and ran to the nearest CVS.

An hour or two and one extraordinarily kind, extraordinarily patient CVS employee later -who very calmly and gently assured me that no, ma’am, the IRS is not going to arrest you in a CVS parking lot today -I found myself sitting in bumper-to-bumper Denver traffic with my brand new puppy (who I now had absolutely no idea how I was going to afford to keep, feed, vet, or otherwise care for), staring blankly into the abyss.

Within roughly eight hours, I had successfully managed to lose my income, lose my health insurance, almost spend what little savings I had on an Indian phone scam, and still had not heard a single word from the dead-end boyfriend.

Surely, surely, this had to be rock bottom. Surely the universe had run out of ass backwards jokes to play on me for one calendar day.

Turns out, the universe had one more level for me to drop.

Before I could even fully react or process the sound, my beat-up Acura MDX slammed directly into the back of the very shiny, very expensive Mercedes that had stopped in front of me. My puppy went flying into the windshield. My head slammed into the horn. And everything went still.

At some point -could have been thirty seconds, could have been thirty minutes, who’s to say -I heard a soft, almost apologetic knock on my driver’s side window. I peeled my forehead off the steering wheel, slowly turned my gaze toward the very nice man now standing outside my window.

He must have taken one look at my face and immediately understood that today was simply not my day, and tomorrow was not looking particularly promising either.

“Are you okay? Is your dog okay?”

I had not even fully registered what had just happened, let alone the fact that my dog was now upside down in the passenger seat staring at me like I had personally betrayed his trust (rightfully so).

I scrambled to grab my insurance card from the glove box and started attempting to flip Oakley right-side up while simultaneously blubbering an unhinged stream of apologies to the kind stranger whose very nice, very expensive car I thought I had absolutely demolished.

“Oh, don’t worry about the insurance, it’s just a car, no real damage on it anyway. Do you want to get out and take a second? I’m happy to call you an ambulance if you need it.”

My disbelief was, apparently, extremely visible on my face- because he started laughing.

“You look like you’ve already had a day. No need to make it any worse.”

So we sat down on the curb outside my very broken-down car and just started talking, while I waited for my ride. And for a complete and total stranger who somehow did not want my insurance information and apparently also did not want to abduct me into the back of a windowless van, he was remarkably kind, remarkably patient, and remarkably attentive.

By the time my ride finally pulled up, Mr. Kind Stranger had essentially heard my entire life story (my therapist has since made me work on not oversharing- I have not, regrettably, improved). I had told him about my career, how I ended up in Denver in the first place, college, the works.

He listened quietly to all of it. And when I finally finished, he stood up, brushed himself off, and handed me a business card.

“You have an inspiring story. I’m the CEO of a fairly prominent tech company here in town. I am certain I can find you a spot on our team. Give me a call sometime and we’ll set up a proper interview - sans car crash.”

When I tell you that my jaw hit the hot Denver pavement, and for one brief, shining, never-to-be-repeated moment in the entire history of my life I was at a complete and total loss for words- there is simply no better way to describe that exchange.

I took his card, fumbled out a deeply embarrassing thank you, and watched him drive away in his only-slightly-dented Mercedes.

And that is the story of how a layoff, an Indian phone scam, and a car accident- all within the span of a single Tuesday- turned out to be the single biggest catapult of my entire professional career.

Stay tuned for the final installment- Part Five.

xoxo
G

I had already been very financially independent for quite some time and this was the first time my eyeballs could literally see a line of sight to a pre-determined and neatly outlined roadmap to Financial Freedom, USA. How was one to turn away from that when just a few years ago, I was walking an hour each way to my minimum wage job in a department store, come hell or high water, in Boston, to make $10 an hour before taxes while paying rent in one of the most expensive college towns in the United States and being a full-time student.

The devil on my shoulder had a megaphone, a podium, and what I can only describe as an unnecessarily aggressive PowerPoint presentation- all dedicated to calling me a dumbass for even considering walking away from the thing that was supposed to fix everything, which was, again, just making more money. The angel on my shoulder was doing her absolute best, speaking in the careful, deliberate tone you reserve for a toddler who is one wrong look away from a full nuclear meltdown, gently suggesting I trust my own path.

Whatever that path was, I genuinely had no idea and that reason was not enough for the still unhinged and still unmedicated anxiety.

So I took the next high paying job, traded the cubicle for a “co-working space,” the faulty headset for personal AirPods, and the burnt coffee for gross nitro cold brew on tap- at a literal cannabis tech company in downtown Denver.

And yes, I mean a tech product that did in fact support the compliance and regulation of sales of the good ole Mary Jane.

My day-to-day consisted of selling into dispensary owners or grow houses, walking around being asked to repeat the pitch a thousand times (for obvious reasons), team meetings that occurred at 4:20 PM (took me too long to put that together), and a slightly “elevated” title with more “theoretical” responsibility. It was my first real stab at some version of leadership in a true Series A start up and I was completely unprepared.

Everyday felt like a systematic tilt-a-whirl that was constantly on fire and I was only given a spray bottle when I needed a firehose to fix things. My youthful confidence (young executive arrogance) didn’t make up for the skill gap that I was slowly realizing I had despite my unrelenting desire to become a good leader. My manager’s background was in engineering and finance, not sales, and despite making 4x of what any of us were making, he couldn’t answer any questions I had and was so soft spoken we never knew if he was mad or happy about anything we did, ever.

(I quickly learned later on in my career that this was a normal trend and it would never not drive me insane. People with little to no relevant background to make them qualified to manage, were able to yap their way to the top when obvious career and skill gaps existed.)

I was pacing hallways, never not connected to a power dialer, and then sprinting to fix a reporting error on a CRM dashboard while YouTubing how to actually fix the reporting error because I didn’t know how and neither did anyone else. I was helping finance and HR configure quotas and budgets, sitting in meetings with people who felt light years ahead of me but quickly realized in all actuality they also had no idea what they were doing- they were just trying to do something that was directionally accurate and financially lucrative.

It was a true cluster fuck and yet, after each hellfire day, I felt like I was gaining skillsets that would have taken me years in bigger structures otherwise.

Every time I was pushed up against any obstacle that was preventing us from moving forward or succeeding, through each teeny tiny micro-win, I was gaining the confidence to tackle problems head on, regardless of having oversight or support. I was learning, in real time, how to look at business gaps in holistic operational perspectives; understanding how each mechanical lever that is pulled within said system has downstream impact. The lessons were becoming invaluable and I loved feeling that important.

I started to become proud of my work.

My mom started to become proud of my work.

Hell, even my therapist, who knew nothing about what I did everyday, was also becoming proud of my work.

So naturally, I developed the fatal flaw mindset that every young leader/manager does when you are that involved and believed that this company would truly FaLl ApArT WiThOut Me and my brilliance and No MaTter What, my job was secure, obviously.

Turns out, they didn’t feel the same way.

Come to find out, business was in fact not “booming” apparently despite the team hitting quotas and everyone saying we were headed to Series B.

Sales were not as great as they anticipated and the investors were getting pissed.

Product was lagging and roadmaps were muddy, and no one had a clear path to understand when things were going to get better.

And so, heads rolled and mine was one of them.

And that my friends is how young, dumb me experienced her first big girl layoff, legitimate panic attack, Indian phone call scam to take my money, and car accident, all in the same day.

Stay tuned for Part Four.

xoxo,
G

It had been six months since I had started my first sales development role for a reputable tech company in Denver and I had volunteered to work the “early morning” swing shift to call on East Coast leads- a.k.a. catch prospects before they went into their own corporate jungle gym, were probably not caffeinated yet, and definitely didn’t want to hear from a sales rep out of Denver yapping at 8 AM.

It was what the sales bro culture commonly refers to as “the grind” and it was in fact just that.

I would be in a cubicle, with a faulty headset, staring at a sales queue that auto refreshed every five seconds on my computer- just waiting for a lead to pop up on a very loud sales floor. Once that little shrivel of hope showed up on my screen, it was an all out war between myself and six other teammates on who could claim the lead first and dial out.

Initially in my head when I took the opportunity, I thought “earlier in, make more sales, earlier out, beat quota- all will be well.”

Turns out all was, in fact, not well.

In the first two weeks, I had at least four or five different clients tell me to “eat glass” (to this day I am not sure why this was a repetitive theme); I had another one who told me that I was calling him during the “mourning period of his dog’s death.” A personal favorite was being told that they wished I got “hit by a car and slightly maimed but not fully ‘because they didn’t want that on their conscience’.” And of course there was also the consistent slew of expletives that would follow after I was done with my pitch and the obvious hang up.

Nothing like getting told to take a long walk off a short pier to build character all before 8 AM on a Tuesday.

Despite its, shall we call them, “growing pain moments” I actually started to excel at the job.

Six months turned into almost a year and I was “sMaSHing mY QuOTA” and I even won some company awards. I somehow had found a way to begin to see the inherent value in the corporate playground and also the inherent value in a daily free lunch. Things were looking up.

Despite the hem-hawing and bitching and moaning, I found myself even enjoying the work and the consistency of a reliable paycheck. I was being asked by other sales leaders to start training new reps, lead team calls and meetings, and even meet with the CRO at the time to discuss my own strategy that was leading to success.

You see, at this point, I had realized that stability of corporate, expletives and early morning burnt coffee included, weren’t so bad. I had a track to follow, a bi-weekly direct deposit, and this thing called benefits. Also my unhinged anxiety loved a good controlling ladder where each step was neatly outlined in a perfect sequential order; all I had to do was follow the steps, sell my soul, and get to golden handcuffs status.

In a what felt like a second, I was nearing almost two years into the role.

I realized this when one day, my manager and team brought over a small cupcake to congratulate my most recent quota accomplishment and asked what my plans were for my next work anniversary.

After the mild cheering and claps on the back, everyone shuffled back to their cubicle and I sat there shell shocked and frozen.

How in the fuck had I been here for this long?

(Realistically it wasn’t that long in the scheme of things but in young, naive twenty something’s me’s mind, it might as well have been a hundred years).

Calling the same people still telling me to eat glass, with the same faulty headset, and barely paying rent and this was considered the dream? Because I had a job right out of college? And I sometimes was able to pay some of my bills and occasionally afford a beer on the weekends? Let me be perfectly clear, this was in fact not twenty-three year old me’s the dream- this was twenty-three year old me’s budget cut version of what post grad life was supposed to be after a cross country move to dramatically and cinematically sTaRt OvEr and FinD mYseLf.

I was supposed to be slinging drinks at night and working on my art all day.

I was supposed to be driving the open roads with some old school playlist like all the movies showed.

I was supposed to be falling in love with some mountain man who would take all of my problems away.

And yes, in all of these what I thought to be realistic fantasies, my bills were a non-issue (no idea how I got to that logic- despite having an almost fully developed frontal lobe and a college degree).

This could not be what my life was going to be for the next forty plus years. Surely there was some glitch in the matrix and at any point, the director who was running this buck wild movie I found myself in, would yell “CUT,” and I would wake up in a life that was actually mine, working towards a career that I actually cared about.

One would think that after this internal existential crisis in the movie, this would be the part where the character busts out of the double doors and into the wild world to go make some drastic life changes to get everything back “on track”.

Spoiler alert, that was not this movie.

Instead I did nothing, pretended that this is what I wanted, and went and found a higher paying job so I could afford more beers on the weekend and stop being late on rent payments.

And turns out my friends, that higher paying job, was the most ass backwards decision I had ever made in my career when it came to chasing the next big paycheck.

____________________________________________________________________________

For twenty-one-year-old, three-months-post-college me, getting my first corporate job was a saving grace- a serendipitous event that kept me financially safe and gave me somewhere to “be” after spending the last sixteen years on some version of a sports, social, and school schedule.

It all started when a nice man I’d never met handed me a diploma in a very hot TD Garden on graduation day (it was likely hot because I was very hungover) and said, “Good luck out there.” In a blink, I suddenly had nowhere to be for the first time in my life.

Unlike many of my recently graduated (and also probably hungover) peers who crossed the stage that day, I decided not to stay in Boston. Instead, I headed west to Denver with two suitcases and basically no dollars to my name. In retrospect, the move was smart. The no dollars part was not.

I spent my first two months in Denver in an “internship” at a museum — eight weeks of a lot of work for a little more than zero dollars.

As the internship wound down and I still had no idea what I was doing, I realized I had two weeks until move-in day with my best friend and no money for the deposit.

Being that broke “seemed cute and cliché for a new post-grad tRyIng to FinD HeRselF oUt wEst,” but it did not feel cute or cliché after the tenth panic attack, endless unanswered résumés, and a negative bank balance.

So naturally, I called my mother.

Being the only daughter out of four children, I was well-versed in the “go figure it out and call me back when you do” method we were raised on. While I appreciated that 90% of the time, this was one of the 10% moments that screamed, “please tell me what to do because contrary to the last six hundred years where I claimed to know more than you, plot twist, turns out I do not SOS please help.”

After my near-hysterical babbling, she was silent for a moment.

“Let me call you back,” she said, and hung up.

I stood in the middle of the street I’d been speed-walking up and down, in disbelief.

I had just spent twenty-five minutes explaining how every plan I had was going to hell, and all forty-five of my backup plans were in the sidecar right next to it- and my mother’s response was, “Let me call you back.”

Mentally, I was setting the world on fire. Emotionally, I felt twelve and stupid. Physically, I threw up on the sidewalk.

Before the dark clouds could roll in and God or whoever was in charge could smite me, my phone rang again. It was my mom.

(Realistically, this all happened in about five minutes, but it felt like five hours.)

“Call this number and ask to speak to Ally. She works at a tech company downtown and said she could refer you for an entry-level sales job- something called ‘sales development.’ Figure it out, because I’m not doing it for you. Love you, bye.”

I didn’t get a word out before the line went dead.

No context. No explanation. Just a number and a name of a job I didn’t understand.

Still standing on the sidewalk, I stared at the number and started dialing furiously. If Ally could help me pay rent, Ally was about to become my new best friend until she signed off on that referral. (I found out later Ally actually got paid for referrals, so I didn’t need to beg/force- but that’s a story for another day.)

I hit dial and waited as Ally held my dramatically fragile fate in her probably very nicely manicured hands.

“Hello?”

“Ally- hey, this is Gracie. My mom shared your number and said there might be an opening for something called ‘sales development.’ I’m looking, can start anytime, and have a résumé ready.” (Translation: please help me avoid another overdraft fee, Ally.)

She paused, then laughed.

“Can you make over 100 dials a day and get told to kick rocks 99% of the time in a cubicle with an unattractive headset?”

I paused. While this wasn’t the plan, it was at least a plan. I’d been made fun of by my brothers for years- how bad could strangers be? (to no one surprise- there were days it was pretty bad, especially the confused elderly who I somehow got ahold of and had to call and definitely did not want to hear from a 21-year-old sales rep in Denver.)

“Yeah, sure, why not- as long as it pays the bills.”

“Cool. Send me your résumé and I’ll pass it to my manager, Josh. I’ll reach out tomorrow with next steps.”

“Sounds great, thank you.”

I hung up with no idea what the hell “next steps” meant, but apparently they were happening. Now all I had to do was wait- and somehow convince my bank to stop over-drafting me into the next millennium until I heard back.