I have read an embarrassing number of side hustle lists.

You probably know the ones.

50 Side Hustles You Can Start Today.

27 Side Hustles That Pay $5,000 a Month.

15 Easy Ways to Make Money From Home.

And somewhere between number three and number thirty-seven, you start wondering whether you should become a virtual assistant, sell printables, walk dogs, flip furniture, start a YouTube channel, become a notary, deliver groceries, freelance, tutor algebra, or groom llamas.

And yes, llama grooming is an actual job.

I know because I did it.

The problem is not necessarily that the ideas are bad.

Some of them are perfectly legitimate ways to make money.

The problem is that the list usually answers the easiest question:

What could I do?

It rarely answers the much more useful question:

What actually makes sense for me?

And after 50, I think that distinction matters a whole lot more.

“You can make $5,000 a month.”

Whenever I see an income claim like that now, my first reaction is:

For who?

Someone who has already been doing it for five years? Someone with an existing audience? Someone working 60 hours a week?

And is this built around a 25-year-old body and energy level, or a 55-year-old one with appointments, family responsibilities, maybe some aches, maybe some hormones doing whatever the hell they feel like doing, and a very different tolerance for nonsense?

Then there’s the money itself.

Is that $5,000 in revenue or actual profit? Is that typical, or is it one unusually successful example being used to sell the possibility?

“Can make” is doing an enormous amount of work in a lot of online income advice.

Technically, I can win the lottery.

That does not make Powerball a retirement strategy.

A legitimate opportunity can still be completely wrong for you

This took me longer to understand than it probably should have.

I spent years looking at income ideas and asking whether they worked.

I should have been asking whether they worked for me.

There is a difference.

I’ve been on Etsy in one form or another for about ten years. Physical products, digital products, different shops, different niches.

Etsy is real.

People absolutely make money there.

I’ve made money there.

And I’ve finally accepted that actively building an Etsy business is not where I want to spend my time anymore.

That doesn’t make Etsy bad.

It means I learned enough about myself, the business model, the market, and what I want my work to look like to say:

Not for me.

That is actually useful information.

I think we need a lot more of that in conversations about side hustles.

Not:

Does this work?

But:

Who does this work well for?

Your actual life belongs in the decision

If you’re 22 and deciding what kind of work to build, you have one set of considerations.

If you’re 52, 58, 61, or 67, you may have another.

Not because we all become fragile little Victorian ladies after 50.

Somebody in their 60s may happily go back to school for several years and start an entirely new profession.

Someone in their early 50s may say, “Absolutely not. I am not taking another exam as long as I live.”

Both are reasonable.

But those preferences matter.

So do things like how much money you need, whether you want predictable income, how much training you’re willing to take on, whether you want to punch a clock or work independently, and how much time and energy you actually want to spend earning.

Do you need physical flexibility?

Do you have caregiving responsibilities?

Is your energy predictable?

Do you want to work with people?

Do you want to build something of your own?

Those things belong in the decision too.

And now there’s another question that belongs in the mix:

How likely is this path to hold up as AI and automation keep changing work?

I don’t think anybody can honestly call a career “AI-proof.”

But I absolutely think it’s reasonable to ask whether a path depends heavily on human judgment, trust, relationships, physical presence, licensed responsibility, or real-world problem solving.

Especially if you’re about to spend months or years retraining for it.

The money needs a job too

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This is another thing those giant lists rarely account for.

“I need to make more money” can mean wildly different things.

Maybe you need an extra $300 or $500 a month so the budget isn’t so tight.

Maybe you’re trying to cover a gap after cutting your hours.

Maybe you were laid off and need to replace a substantial income.

Maybe you’re still employed but no longer comfortable having every financial egg in one paycheck basket.

Maybe retirement is getting closer and the numbers aren’t where you hoped they’d be.

Those are not the same problem.

So why would they automatically have the same solution?

A flexible little supplemental income stream might be fantastic for one person and completely inadequate for another.

A longer-term creator business might be worth building for someone who has time and wants autonomy.

It is a terrible answer for someone who needs reliable grocery money immediately.

The question shouldn’t start with:

What side hustle is hot right now?

It should start with:

What does this money need to do for me?

Sometimes the answer is a job

I think this matters too.

There is so much internet content built around escaping jobs that we can start acting like employment itself is failure.

It isn’t.

Some people want a paycheck.

Some people want benefits.

Some people like knowing exactly when they work and exactly what they’ll be paid.

Somebody may go through this entire decision process and realize that what they actually need right now is a good part-time job, a remote position, or a short certification that leads to dependable work.

Wonderful.

The point is not to turn everybody into an entrepreneur.

The point is to make a better decision.

And sometimes one path can become several

This is the part I find especially interesting.

A person might start with one straightforward income path and later discover several ways to build around the same skill.

Take bookkeeping.

Maybe the first income is simply bookkeeping for clients.

But that knowledge could eventually branch into cleanup projects, software setup, specialized bookkeeping for a particular industry, templates, workshops, a bookkeeping social media channel, affiliate income from tools they already use, or other services.

Does everybody need to do all of that?

God, no.

We are not building ourselves seven new jobs.

But I like the idea of seeing the possibilities around a skill instead of assuming one skill must equal one paycheck forever.

Some people will want one simple income source.

Others will want a mix.

The choice should be theirs.

I think we need a better starting point

We do not have a shortage of income ideas.

What we don’t have nearly enough of is help figuring out which ones are worth our particular time, money, energy, and attention.

That’s the problem I keep coming back to.

Not “What side hustle is hot right now?”

Not “What can technically make money?”

But:

What makes sense for this person, in this life, at this stage?

That’s a much better place to start.

And I think it leads to better choices, less wasted time, and a lot less beating yourself up because someone else’s perfect opportunity turned out to be a terrible fit for you.

That is the kind of help I’m interested in building.

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I’ve been thinking lately about how much of my life I’ve missed because I was either too big or too broke to do things.

The too-big part is almost funny now because there were plenty of years when I thought I was enormous and, looking back, I was just...a perfectly normal-sized woman with a terrible opinion of herself.

The too-broke part, unfortunately, has receipts.

A lot of us hit our 50s and suddenly need to rethink how we’re going to make money.

Maybe you got laid off.

Maybe you were pushed out.

Maybe health issues made your old job impossible.

Or maybe you’re looking at another five, ten, or fifteen years in a job you can’t stand and thinking, I have got to find another way.

That’s when side hustles and online income stop sounding like cute little hobbies.

They start looking like options.

I’ve spent plenty of my own life putting things off because I felt too big, too broke, too anxious, or not quite ready yet.

Post-menopause me is increasingly less interested in waiting for some improved future version of myself to appear before I try something.

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Which brings me to YouTube.

Why YouTube After 50?

I’m not interested in YouTube because I have a burning desire to become an influencer.

I’m interested because YouTube is another possible way to build income that doesn’t require an employer to choose me first.

And people our age are already there.

According to Pew Research Center, 85% of Americans ages 50 to 64 use YouTube, and 64% of adults 65 and older use it.

That’s a whole lot of us feral, hose water drinking folks!

Of course, watching YouTube and putting your own face on YouTube are two different things.

Some of us worry about looking old, sounding awkward, or attracting trolls.

People online can absolutely be jackasses. But you could be a 21-year-old beauty queen rescuing puppies and somebody would still show up to tell you your eyebrows are wrong.

There is no troll-proof version of you.

So I’d rather ask the more useful question:

Is YouTube a Good Income Option After 50?

This is the bigger question.

Because simply learning that something can make money isn’t enough.

I want to know whether it makes sense for the person considering it.

Here’s my quick read on YouTube:

Startup cost: Can be low
Speed to income: Usually slow
Schedule flexibility: High
Physical demands: Generally low
Learning curve: Moderate
Income potential: Highly variable, with several possible ways to earn
Best fit: Someone willing to create consistently and build over time
Poor fit: Someone who needs dependable income immediately

Those are the questions I want us asking about any income option:

What does it cost to start?

How long might it take to pay?

How flexible is it?

What does it require from me physically and mentally?

How many different ways could it eventually generate income?

Does it fit the life I actually have now?

That’s a much more useful question than:

Can somebody on the internet make money doing this?

Somebody can make money doing almost anything.

That doesn’t mean it’s right for you.

YouTube Just Changed What Counts as a View

I recently wrote about YouTube’s upcoming monetization changes and what they could mean for smaller and newer creators.

Read it here: YouTube Just Moved The Goal Posts

Apparently YouTube wasn’t finished rearranging the furniture.

Beginning August 24, 2026, YouTube will count a public view from the very first frame a video plays.

Not 30 seconds.

Not 10 seconds.

Not even one full second.

If the video starts playing, it counts as a public view.

YouTube says creators may see their visible view totals rise faster under the new system.

But a bigger public number does not necessarily mean more people actually watched.

Public Views and Engaged Views Are Different

The simplest version is:

A public view means the video started.

An engaged view tells you someone went beyond that initial exposure.

If somebody only sees your thumbnail and the video never plays, that’s still an impression.

Once it starts playing, you have a public view.

Then the other metrics start telling you whether the person actually stayed.

Impression → Public View → Engaged View → Watch Time → Subscriber → Returning Viewer

That distinction matters.

A video could show 5,000 public views while having far fewer engaged views.

Those numbers are answering different questions:

Did YouTube put this in front of people?

And:

Did those people care enough to stay?

Why This Could Be Good for Smaller Creators

There are three parts of this change I find useful.

Bigger visible reach

YouTube says public view counts may grow faster.

For a brand-new channel, that could make the early days feel a little less like performing your masterpiece in an empty VFW hall.

A video showing 600 views looks different to a human visitor than one showing 75.

That does not mean YouTube has said bigger public numbers automatically lead to more recommendations.

But humans see those numbers too.

Better information about exposure

There’s a big difference between:

YouTube isn’t showing my video to anyone.

and:

YouTube showed my video to 5,000 people and most of them fled the scene.

One may be more painful, but both are useful information.

If reach is low, maybe the problem is the topic, title, thumbnail, or audience fit.

If reach is strong but engagement is weak, maybe the opening isn’t working or the video isn’t delivering what the title promised.

At least now you have a better idea which problem you’re trying to solve.

Better reach data for sponsors and brands

YouTube also says the new public-view system may help creators communicate their reach and value to brand partners.

That’s important because YouTube income isn’t limited to ad revenue.

A channel can eventually support several ways of earning:

• Advertising

• Affiliate links

• Sponsorships and brand partnerships

• Digital products

• Services

• Memberships

• Leads to another business

That’s where YouTube becomes especially interesting to me.

One audience can potentially support several income streams.

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What Changes and What Doesn’t

The graphic covers the important distinction here: public views may rise faster and reach may become easier to measure, but that does not suddenly make every view valuable or change the requirements for YouTube’s Partner Program.

It Doesn’t Directly Change Monetization, but It Can Still Matter for Income

The new first-frame view does not lower YouTube Partner Program requirements or turn every autoplay into money.

But it can still help creators financially by giving them:

• Bigger visible reach

• Better evidence of exposure

• Potentially stronger social proof

• More useful data for brands and sponsors

• A clearer picture of whether their content is actually being surfaced

• A better sense of whether YouTube is worth continuing as part of a larger income stack

That’s the distinction I care about.

The new view count doesn’t make YouTube instant money.

It may make YouTube a more useful business asset.

If you’re using the platform to attract sponsors, earn affiliate income, sell a product, build an email list, or send people toward another part of your business, reach matters.

So does knowing whether the platform is actually putting your work in front of people.

Maybe Current Me (And You) Gets a Turn

I’ve spent plenty of my life putting things off because I felt too big, too broke, too anxious, or not quite ready yet.

Post-menopause me is increasingly less interested in waiting for some improved future version of myself to appear before I try something.

That doesn’t mean chasing every side hustle that crosses my screen.

It means getting better at looking at an opportunity, figuring out what it costs, what it might return, whether it fits my life, and then deciding whether it’s worth trying.

Because a lot of us are in a strange place right now.

We may be done with traditional work.

Traditional work may be done with us.

But we’re not done needing money.

I’m less interested in finding one perfect thing that’s supposed to solve everything.

I’m interested in building options.

YouTube might be one of them.

Gray hair, wrinkles, anxiety and all.

And if somebody doesn’t like my eyebrows, they’ll survive.

Sources

• Pew Research Center. Social Media Fact Sheet. 2025. Data on YouTube usage among adults ages 50 to 64 and 65+.

• YouTube. Official August 2026 announcement explaining the change to first-frame public view counting, engaged views, creator metrics, and implications for brands and sponsors.

• YouTube Official Blog. What Are Engaged Views? August 2026. Explanation of impressions, public views, engaged views, and how the updated view system works.

• YouTube Help. YouTube Partner Program Overview and Eligibility. Official requirements for qualifying watch hours, Shorts views, and monetization.

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Don’t freak out just yet.

I’ve been seeing some real meltdowns this week from folks lamenting the upcoming changes to the YouTube monetization program. Yes, come February 1 2027, if you have not already been accepted in the YouTube partner program, it will be harder for you to hit that goal. But here’s the thing: You’re not a quitter and some of you haven’t even started yet. We’re Gen X for cripes’ sake, so we’re used to obstacles and we always seem to figure shit out. It’s just what we do.

So, if you’ve been putting off starting a YouTube channel, the clock on the old, easier rules just started ticking.

Now these numbers aren’t about creators over 50. They’re about users and viewers over 50. That is a huge audience just waiting for content specifically aimed at them and their interests. As a creator over 50 you have a huge opportunity just sitting there waiting for you.

It’s going to get harder the longer you wait, but even after February 1 2027 you still have a massive audience available to you.

On August 10, 2026, YouTube announced it’s doubling the bar to get into the YouTube Partner Program, the tier that unlocks ad and Premium revenue sharing. The change takes effect February 1, 2027. Right now, getting in requires 1,000 subscribers plus either 4,000 watch hours in the past year or 10 million Shorts views in 90 days. Starting February 1, that doubles to 8,000 watch hours or 20 million Shorts views. The subscriber requirement stays at 1,000.

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Who this actually affects. Anyone already in the Partner Program before February 1 isn’t subject to the new 8,000-watch-hour or 20-million-Shorts-view entry threshold. This is membership-based, not hours-based: having a channel that’s been live for years, or quietly banking watch hours without applying, doesn’t grandfather you in on its own. What matters is being approved into YPP before the cutoff. If you’re planning to start and apply, the math changes for you specifically. If you’re already in, this particular change doesn’t affect you.

The rules for Shorts are changing too. Starting the same date, Shorts monetization gets its own separate, ongoing requirement: 10 million qualified Shorts views in the trailing 90 days, every 90 days, just to keep earning from Shorts. Fall below it and you don’t lose your YPP status, you just stop earning from Shorts specifically until you cross the line again. This isn’t a one-time hurdle like the entry bar. It’s a moving target you have to keep hitting, which is worth knowing before you build a whole strategy around Shorts alone.

So should you rush to start a channel before January 31? Maybe, but not for the reason you’d think. You’re not racing to hit 4,000 watch hours in four months either. That’s not the finish line. Watch hours are measured on a trailing 12-month window, not a lifetime total, so what actually matters is building sustained, recent viewership, not a one-time cumulative number. What you’re racing is approval. If you start now, publish consistently, cross the threshold, and are accepted into YPP before February 1, this particular increase won’t apply to you. If you’re not ready by then, you’ll be judged under the new, doubled numbers whenever you do apply, regardless of when you first hit record.

The AdSense obsession is the wrong goal anyway. A lot of people treat YouTube Partner Program acceptance as the finish line. It isn’t, and chasing it as the only reason to be on YouTube sets a lot of people up to quit before they’ve built anything. Creators over 50 are doing genuinely well on YouTube right now, and ad revenue doesn’t have to be the whole plan, especially for creators building a business around their channel. Affiliate links you place yourself in your video descriptions, merchandise, and YouTube’s own lower 500-subscriber tier (which unlocks channel memberships, Super Chat, and select Shopping tools once you hit 500 subscribers, 3 uploads in 90 days, and either 3,000 watch hours or 3 million Shorts views) are all still on the table regardless of these new rules, and that lower tier isn’t changing under the February update. Ad revenue is one channel of several, not the whole business model.

The irony I’m not going to pretend isn’t there. I’ve been talking about starting a YouTube channel for a while now, and here I am writing about other people’s timelines instead of my own. I’m seriously looking at the end of September for myself. Babies crawl before they walk. Audiences take time to build no matter when you start, and every month spent waiting is a month not spent building. That applies to me as much as it applies to you.

The bottom line: if YouTube’s on your radar at all, this is a reasonable nudge to stop circling and start. Not because of a hard deadline that ends your chances. Your chances don’t end. The entry bar just goes up. But five months of runway to get in under the current, lower numbers is a real, finite window, and waiting doesn’t make the math easier.

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Sources: YouTube’s own announcement is the most authoritative account of these changes, posted to the YouTube Blog on August 10, 2026. Additional reporting and the trailing-window and fan-funding details referenced above came from vidiq’s breakdown of the changes and Search Engine Journal’s coverage of the new terms.

I’m CK, and after leaving my job at 58 because of unexpected health issues, I found myself looking for jobs and side hustles I could do from home. I started digging into the market for folks over 50 and found so many people that were struggling to find new gigs to replace jobs they’d been let go from or had to leave like I did. Retirement can be hard enough these days, but finding yourself unexpectedly retired due to circumstances beyond your control is even harder.

I’ve set out to research and write about jobs and side hustles that people over 50 can do that can also honor their time and health. Some are just for a little extra money when you need it, others are full-blown career pivots. So if this is where you are in life right now, come sit by me and let’s talk about it.

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What you’ll find here:

• Real research on income paths for people 50+, no hype, just data

• Certification and career deep dives (real cost, real time, real catches)

• Personal, honest posts about doing this myself, mistakes included

A few places to start:

• $21 an Hour to Owning Your Own Business

• Winging It at 59 Without a Manual

• Nearly 40% of Americans Are Already Working in the Freelance and Gig Work Economy

The freelance and gig economy now makes up roughly 39% of U.S. workers, up from 53 million Americans doing this kind of work back in 2014 to over 70 million today. That’s not a fringe trend anymore, that’s almost 2 out of every 5 working Americans. COVID showed a lot of us something we couldn’t unsee, the world and the economy can shift in the blink of an eye. There are some things that will never be the same again and counting on a job, a check or a retirement are just three things that have been forever changed.

Grind culture has been around for a couple of decades. It is capitalism’s favorite costume, dressed up as the idea that nonstop hours and constant productivity are the guaranteed road to success. Exhaustion isn’t a personality trait I personally want to cultivate, no matter how many people are trying to sell it to me.

The ways to make money, especially when you’re over 50, have changed, and there’s definitely some pros and cons to this new era. The reason I’m doing this, the reason I am researching ways to make money, isn’t to push a hustle culture mentality but to deliberately and literally find ways to make money that also prioritize my mind, body and soul. This isn’t some touchy feely talk, but at this stage of life, self-care can be an act of rebellion. To decide to use your time learned, hard-earned wisdom and skills to forge a new path is actually radical when you think about it.

That doesn’t mean any of this is easy. Some of these paths take real time, real study, real stretches of difficulty. But there’s a real difference between effort you’re choosing, at a pace you set, toward something that’s actually yours compared to a grind you’re trapped in with no say in the terms. One builds something sustainable while you age and the other just burns you down while telling you it’s virtuous.

I think about a man I used to work with at my last job. He’s about nine years older than me so he’s around 69 now. You can see the decades of hard physical work and his body carries every one of them, stooped at the waist, a shuffle in his walk, clearly uncomfortable most days, physically and otherwise. He worked hard his whole life. He’s dragging himself to a job he hates and knows there is no real path there for him to move up or make much more than he does today. He’s also terrified of losing that job even though it continues to beat up his body and drag him down mentally. He knows about ageism and knows there won’t be anyone knocking at the door to offer him a job if he quits. I don’t want that. My body is paying a price right now for working too long for too little in return and I want options that protect me, provide for me and don’t cause anymore harm.

And it’s not just bodies bent by physical labor. I’ve watched it happen to someone I love, worn down by a toxic work culture that never clocked out, hours stuck in front of a screen well past when the day should’ve ended, salaried so the overtime was the norm. Same damage, different shape. There is no reward for beating your body up, whether that’s decades of physical strain or years of unpaid extra hours you were guilted into thinking you owed someone. Whoever decided that breaking yourself was a virtue was just trying to get more work out of you for less.

My 78 year old neighbor still believes that if your body isn’t wrecked, you never really worked. That’s not wisdom. That’s a life spent being convinced the damage was the point.

Here’s the real irritation: not one of these people is wealthy. Not even close. Every single one of them is still struggling financially, right now, after everything their bodies and minds already paid. So what was it actually for?

I have seen so many people, mostly women at this point on Substack, Youtube and Facebook talking about reinvention after divorce, after layoffs, after being pushed out or pushed around at a job that no longer suits them physically or mentally. My answer was to start researching and find options I could build for myself and share them with others in the same position. The only caveat is you have to actually start doing and not just researching. No analysis paralysis allowed! You have to pick something and give it a whirl. Dip your toe in the water and if it doesn’t fit, you’re allowed to pivot as many times as it takes to find what actually works for you.

I also want to be honest and acknowledge something here: not everyone is in a position to step back and figure out what works for them. I’m not either, not entirely. I have a husband who supports me financially and emotionally through this, and even with that, things are tight. I’m juggling bills and due dates right along with everyone else. I’m not writing this from some place of ease where money isn’t a real, constant pressure. I’m writing it because even in the middle of that pressure, I still believe the choice of how to build something matters, not just whether you’re struggling while you do it. I’m not concerned with only my success, I’m concerned about other women and frankly, anyone else that finds themselves in this stage of life.

Here’s how I see it: something has to fall for something else to grow. Old models don’t usually end because everyone stopped trying, they end because the conditions underneath them changed. I can’t prove that’s exactly what happened here, I’m not an economist. But I’ve read enough of the actual data to know that freelancing has grown from 53 million Americans in 2014 to over 70 million today while job security for people 50+ has eroded in measurable ways. I feel pretty confident that the old ground isn’t coming back the way some people are still waiting for it to.

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Damn near 40% of American workers already know this, whether they chose it or landed in it. I’d rather be one of the people who looked at that number and asked “okay, so what do I actually want to build in this version of the world,” than one still waiting for the old one to return.

Something else is already here, on the other side of that grief, if you’re willing to build it on your own terms instead of someone else’s clock.

Hey, I’m CK and if we haven’t met yet, I’m a woman that had to leave the workforce at 58 after unexpected health issues. I had to look for ways to make money that were also compatible with this new stage of life I suddenly found myself living. Now, I research and write about real income options for people over 50 navigating job loss due to layoffs, downsizing or health problems. If that’s where you are right now, grab a coffee and let’s talk about it.

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Every list of “easy ways to make money after 50” seems to recite the same three or four names. I almost put a few of them in last week’s post myself, until I actually dug into the real numbers instead of trusting the reputation. Here’s what I found, and why I’m telling you to skip them, or at least go in with your eyes wide open.

Transcription Work

This one shows up everywhere because it sounds perfect on paper: work from home, no degree, just type what you hear. I actually applied for a transcription job myself years ago, so I know firsthand it’s not the easy on-ramp it’s made out to be.

Getting accepted isn’t automatic. Most platforms require passing a grammar quiz and a graded test transcript before you’re even let in, and rejection is common. Once you’re in, pay runs about $0.30-1.10 per audio minute, not per working minute. A messy 60-minute recording can eat 3-4 hours of your actual time to transcribe cleanly. The average transcriptionist completing 15 jobs a month earns around $156; the top 5% earn closer to $900. That’s not nothing, but it’s a low-hourly-rate grind that rewards speed and clean audio, not the quick easy win the internet promises.

Verdict: Real, but go in knowing the acceptance bar and the real math before you count on it for anything.

Freelancing on Upwork

“Just freelance on Upwork” gets repeated so often it’s basically a reflex answer at this point. The problem isn’t that the platform’s a scam, it’s that it’s genuinely one of the most crowded, race-to-the-bottom marketplaces out there. Without a defined niche, you end up competing on price against people willing to work for a fraction of what your skills are worth, and that’s before you’ve paid for the “connects” Upwork charges just to submit a proposal.

Verdict: Workable if you already have a specific, differentiated skill and a plan to niche down hard. Not a good first stop for someone just starting to test the waters.

Renting Out Your Car (peer-to-peer car sharing platforms)

I almost put this on last week’s low-barrier list myself, it sounds like the easiest passive income idea imaginable: your car sits in the driveway anyway, why not let it earn something? Then I actually looked into what hosting really involves.

Most personal auto insurance policies exclude coverage the moment your car is rented out through one of these platforms, and the built-in host protection plans often only cover part of the cost, leaving you to absorb thousands in damage yourself. There’s also a documented pattern of disputed damage claims, hosts and renters disagreeing over what happened and who’s responsible, with real money on the line either way. And beyond the financial risk, handing your car keys to a stranger for days at a time carries a level of personal risk that’s worth sitting with honestly before you decide it’s worth the extra income.

Verdict: What looks like passive income is actually real financial risk, and a level of personal risk most people don’t think through before signing up. I’m not recommending this one.

Here’s the actual point of this post: not every job that shows up on every list deserves to be there. Some earned their reputation. Some just got repeated so many times nobody stopped to check if it still held up. My job is to research, and tell you honestly what I find, even when the answer isn’t what the internet wants to hear.

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I’m CK. I left my job at 58 after unexpected health issues forced me to leave my last job so I had to look for ways to make money that were also compatible with this new stage of life I suddenly found myself living. Now, I research and write about real income options for people over 50 navigating job loss due to layoffs, downsizing or health problems. If that’s where you are right now, grab a coffee and let’s talk about it.

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~CK

You send out resume after resume and hear nothing back, not even a rejection, just silence, like the thing you spent decades building never existed. A layoff, a downsizing, a health scare that knocked your plans sideways, and suddenly the 9-5 you knew how to navigate for thirty years doesn’t want you back. It’s defeating, and it’s not you, it’s time to stop waiting for someone else to say yes and start looking outside the box you’ve been living in for decades.

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I talk about the research I do regarding how to pivot in your 50s and create your own income streams. There are some common things that many of the people I’ve read about do before they made the decision to pursue a specific path. Virtually none of them just jumped headlong into the first thing they thought would make them a ton of money.

Here’s some of the most common steps I see in my research:

1. Create two columns on a piece of paper. A “what do I want” side and a “what can I actually afford (both time and money) to do right now” side.

2. Figure out your financial, physical and time constraints first before you do anything else. You have to make sure that whatever path you choose fits you and your budget.

3. Think about what you could do that would require the smallest first step. This process is a journey to figure out what really works for you and there’s a pretty good chance you’ll change your mind a few times before you decide the actual path. So, don’t get too hung up on trying to find the biggest payoff just yet.

4. Dip your toes in the water before making any big commitments. Find someone or better yet, several someones who are doing the things you are interested in pursuing. Read their Substack, go to their YouTube, Instagram or Facebook. Ask questions!

5. You learn more by actually doing than overthinking. Don’t get stuck in analysis paralysis and over complicate this process. Pick something and try it for just a week and see how it feels. You are not obligated to make a lifetime commitment here so test those waters.

Remember this, clarity will come after action and not the other way around. You’ve got to actually do the thing first to know if it’s the right fit for you.

Here’s also something to keep in mind while you start testing the waters: low barriers to entry is exactly why the most common paths get crowded fast. If something requires almost no certification, no big upfront cost, and no specialized training to start, that also means almost anyone else can start it too, which is precisely why certain jobs show up on “easy to start” lists constantly. That doesn’t make them bad choices, it makes them good choices for the testing phase, low-risk ways to find out if a direction fits you, but it’s worth going in with real eyes open that “easy to start” and “easy to stand out in” are two different things.

The paths with a real barrier, a certification, specialized skill, or genuine experience behind them, usually pay better and face less competition precisely because fewer people can or will do the work to get there. Neither is wrong, they’re just different bets: low barrier gets you moving and learning fast, higher barrier gets you fewer competitors once you arrive.

Quick note before the list: obviously this is only a tiny fraction of what I’ve learned so far. I’m building a full research library of these over on my website, real numbers, real time costs, real catches, one path at a time. What’s below is just a taste of what’s coming, the stuff I’ve dug into so far.

None of these will make you rich. The income potential across this list varies a lot, from a modest part-time supplement to a real full income once you're established, but every single one takes real time and effort to build, and none of them is a shortcut to easy money. If something promises fast riches for little work, that's probably a good sign to walk away.

A few low-barrier options worth knowing about, if you want to start there:

• Mock juror / trial consulting — Attorneys pay everyday people to review case summaries and give their honest verdict before a real trial, sites like eJury and OnlineVerdict have been doing this for over 20 years. Online reviews pay $20-60 for 30-60 minutes; virtual or in-person mock trials can pay $200-700 for a longer session. No experience needed, just a U.S. citizen, 18+, willing to read a case and share an honest opinion.

• Teach English online — Worth an honest correction here: the platform most people remember, VIPKid, largely collapsed in 2021 after a Chinese regulatory change, and now operates in a smaller form as VIPTeacher, paying $14-22/hour. You’ll need a bachelor’s degree (in any field, doesn’t have to be education), but no teaching certificate required if this is just supplemental income.

• Product demonstrator — In-store work sampling and showcasing products at grocery stores, warehouse clubs, and retailers. Averages around $21/hour, no experience required, training provided, flexible part-time scheduling. CDS.com is where you can find demonstrator jobs at Costco. One honest note: this is on-your-feet work, setting up a station and standing through the shift, worth factoring in if standing for hours is a real limitation for you.

Now, if you’re the kind of person who wants to skip straight to something with real staying power, here’s a closer look at three paths on the other end of that spectrum, more upfront cost and time, but real barriers that keep the field from getting crowded.

Enrolled Agent

Let’s clear up the biggest misconception first: an Enrolled Agent doesn’t work for the IRS. The credential comes from the IRS (it’s the highest one they grant), but earning it makes you an independent, private practitioner who represents taxpayers against the IRS, not a federal employee. If IRS layoffs and agency turmoil are making you hesitate on this one, that’s actually backwards, a more chaotic, understaffed IRS is exactly when people want a qualified advocate in their corner instead of facing it alone.

Certification: Passing the three-part IRS Special Enrollment Exam (SEE).

Where: Administered through the IRS; the exam vendor changed from Prometric to PSI Services as of March 2026.

Cost: $350 per exam part in 2026 ($1,050 for all three), plus PTIN (~$19), enrollment application ($67), and study materials ($150-800). All-in: roughly $1,200-2,200.

Time: Most candidates pass all three parts within 12-18 months of study, plus another 60-90 days for IRS processing after passing. Total: 12-24 months typical.

What you’d actually do with it: Run your own independent tax practice from home, on your own hours, no firm or office required. Core services include tax preparation and planning, IRS audit representation, and back-tax/debt resolution. You can also join a CPA firm if you’d rather have steadier income, EAs work inside firms too, no CPA license required, though most EAs choose to stay independent.

Do you need to be an accountant? No. The EA and CPA credentials are entirely separate, non-competing tracks. The EA credential exists specifically for people who don’t want the CPA’s accounting-heavy coursework.

Don’t people hire a tax attorney if they’re audited? Sometimes, but not usually. All three, EAs, CPAs, and tax attorneys, have equal, unlimited legal rights to represent you before the IRS. For most standard audits, an EA is typically sufficient and more affordable than an attorney. Attorneys become the right call when things escalate into genuine legal territory, liens, wage garnishments, or actual Tax Court litigation.

Why it fits after 50: No degree, no age restriction, no prior experience required, decades of filing your own taxes is a real head start. It’s one of the only credentials on this list with unlimited federal practice rights nationwide, and unlike purely seasonal tax prep, audit and resolution work happens year-round.

Medical Billing and Coding

The AI worry first, since it’s the honest question anyone will have these days: this field is genuinely more AI-resistant than most, and it’s not just human judgment holding the line, it’s the law. U.S. healthcare compliance and audit requirements build human accountability directly into the process, that’s not something a model can simply take over. The market backs this up: the medical coding market was valued at $16.5 billion in 2021 and is projected to grow at a 10.6% compound annual rate through 2026, real demand growth, even with AI tools already in production use across the industry.

Certification: Certified Professional Coder (CPC) through AAPC.

Where: AAPC (American Academy of Professional Coders); membership required to sit the exam.

Cost: AAPC membership ~$175-230/year, exam fee ~$300-425. All-in for a first try: roughly $500-700.

Time: The exam itself is 4 hours, but real prep commonly runs a few months. Honest catch worth flagging: AAPC recommends 2 years of coding experience for full CPC status. Without it, you hold CPC-A (apprentice) status until you log that experience, many coders take an entry-level role first specifically to accumulate those hours.

Do you need a medical or nursing background? No. This is a common assumption that isn’t true. It’s learnable from scratch.

What you’d actually do with it: Fully remote work is standard, physician offices, outpatient clinics, billing companies, and health systems all hire coders. CPC holders report just 2.5% unemployment, well below the national average.

Why it fits after 50: Fully remote-capable, genuinely growing demand, and the detail-oriented precision this work requires plays directly to skills many people already carry from decades of adult administrative life.

End-of-Life Doula

The biggest misconception first: this isn’t a medical job, and it isn’t the same as hospice work. A hospice team handles the medical side, medications, clinical care. A death doula provides non-medical, holistic, presence-based support, companionship, easing fear, sometimes just sitting with someone so they’re not alone.

Certification: No single regulated body, the profession itself is unregulated. Reputable paths include INELDA training paired with the NEDA Proficiency Badge, or The Dying Year’s certification process.

Where: INELDA, NEDA, The Dying Year, or university-affiliated programs like UVM’s professional certificate.

Cost: Legitimate structured training runs $725-1,195. If pursuing the NEDA Proficiency Badge, add the exam fee ($115) and NEDA membership ($50). All-in: roughly $900-1,300. A word of caution: cheaper $189 online options exist but carry far less recognition.

Time: Legitimate programs run 6-8 weeks, several hours a week, live and cohort-based. Be wary of anything advertising a 2-week certificate.

Is this AI-proof? About as much as any job can be. This work is entirely about physical and emotional presence, there’s no version of this that gets automated.

What you’d actually do with it: Build an independent practice supporting individuals and families through the dying process. Most doulas work privately with clients, though some partner with hospice organizations.

Why it fits after 50: Lived experience isn’t just helpful here, it’s close to the actual qualification. Most people don’t have real comfort sitting with mortality and grief until they’ve lived enough life to have faced it themselves. That’s exactly why competition is genuinely thin relative to the credential cost.

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That’s the shape of it: figure out your constraints, pick the smallest first step, and don’t wait for certainty before you move, it comes after, not before. Whether that first step is a week testing mock jury work, or a longer road toward something like being an Enrolled Agent, a medical coder, or an end-of-life doula, the point is the same. You don’t have to know the whole path. You just have to take the first honest step down it.

If any of these three sparked something, even a small “huh, maybe,” that’s worth paying attention to. That’s usually how it starts.

If this was useful, here’s how you can help it reach someone else who needs it too:

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• Subscribe if you haven’t, so you don’t miss what I dig up next

• Comment and tell me which one of these you’d actually consider, or what you’re already testing yourself

• Like this post so more people see it

• Share or restack it with someone in your life who’s staring down their own reinvention right now

~CK

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Nearly 40% of all divorces now happen to people 50+. That’s 4 out of every 10 divorces happening right now. If that’s you, there’s a good chance you’ve already realized there’s no handbook for navigating this stage of life. Especially the money stress, and the work of rebuilding an identity after years where being a spouse, and maybe a parent, took up so much of who you were.

It feels heavy just reading that, and it’s totally fair if you feel the same way. Menopause alone would be enough to navigate in a decade. Add a gray divorce, maybe kids leaving home around that same handful of years, and you’re not managing one transition, you’re managing three at once, all while still trying to earn a living. And speaking of earning a living, some are also dealing with job loss or an unplanned early retirement due to health reasons. And maybe none of that is even your specific story. Maybe your marriage is solid and your kids left home decades ago, but the money’s tight and health issues mean building your own income from scratch is simply where you’ve landed. That counts too. You don’t need a dramatic reason to be standing at this crossroads. Needing things to be different is reason enough. That’s genuinely a lot, however you got here. It’s supposed to feel like a lot, because it is. I’m not going to pretend otherwise just to try and keep this post upbeat.

If you’re reading this right now, you’ve literally already survived every hard thing that’s happened to you so far. All of it. That’s not a hype line, that’s just facts. As rough as it may sound, know that this stretch of life isn’t only loss stacked on loss. For many women it’s the first real chance in decades to ask themselves, who am I when I’m not managing everyone else’s needs first? That question can be terrifying and genuinely exciting at the same time. Both are allowed to be true.

Saving money by cutting back can only close part of the financial gap many are feeling right now. Real average hourly earnings actually fell 0.7% between May 2025 and May 2026, while rent and housing costs climbed 3.4% over that same year, and grocery prices rose 2.7%. That’s not a discipline problem. The floor keeps rising while the paycheck buys less than it did last year. At some point, the math stops being about spending less and starts being about earning more.

So where do you even start? Not with a five-year plan, and not by picking a lane before you even know what roads exist. Start smaller. Today, make a list of what you’re actually curious about, not what’s practical yet, not what pays well yet, just what genuinely pulls at your attention when nobody’s watching. No filtering. That list is the real starting point, no matter which direction it points. I put together a simple worksheet for exactly this, free, no email required, no strings attached, just space to actually get it out of your head and onto paper. Grab it below.

The Curiosity List — Midlife Side Hustle

147KB ∙ PDF file

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I’ve been down the research rabbit hole on exactly this lately, and found real women who took wildly different roads and are thriving on every single one of them. Julie England left a career as a tech executive and picked up a paintbrush for the first time after retiring. Ceil Hovey enrolled in nursing school at 71, forty years after her first graduation from that same college. Bonnie Garmus published her debut novel, Lessons in Chemistry, at 65, and it became a bestseller and a TV show. Artist, nurse, novelist, and that’s three directions out of dozens. None of them had it figured out at 50, they just started with a version of that same list. That’s exactly the kind of real, researched direction I’ll keep digging up here every week, and soon on my own website too, so you’ll have somewhere to actually go looking when you’re ready.

Sources

Wages, rent, and groceries: U.S. Bureau of Labor Statistics, Real Earnings and Consumer Price Index news releases, May 2026 https://www.bls.gov/news.release/realer.nr0.htm https://www.bls.gov/news.release/archives/cpi_06102026.htm

Julie England: Prime Women https://primewomen.com/career-and-business/featured-women/career-change-after-50/

Ceil Hovey: Nurse.org https://nurse.org/news/ceil-hovey-71-year-old-nursing-student/

Bonnie Garmus: Barbara Tanner Wallace https://barbaratannerwallace.com/2023/03/five-women-authors-over-fifty/

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If you haven’t subscribed to my Substack yet, I’d really love it if you’d do that now. Don’t forget to like and restack if this post resonated with you.

~CK

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If you’re new here or if it’s been a minute, I’m CK. I live in Montana with my husband, two cats who run the place, and a long-standing dream involving a dachshund ranch that I’ll tell you about another day. I write Midlife Side Hustle for people aged 50+ who’ve been pushed out of traditional work, laid off, aged out, sidelined by health or caregiving, upended by divorce, and who need real income options not motivational posters.

I recently locked myself into deep research mode for about two weeks. I was following trail after trail of information on side hustles that actually work for an older body, an older mind and a spirit that just wants to live authentically while still paying the bills.

My original plan for my Substack was to document myself building my own income streams after health issues sidelined me at 58. That plan melted away after my research bender. The deeper I dug, the bigger the topic got until it was obvious: there was no way I could personally try, test, and report on all of this myself.

Ultimately, my goal with Midlife Side Hustle was to help me create a stable monthly income to replace my former income and at the same time help other folks that may have found themselves in a similar predicament. I set out to write a guide about certifications and training programs that could realistically get someone back to earning; the real costs, the real time it takes, whether the pay is what the ads promise or what the fine print actually says.

One guide turned into two. Two turned into seven. Somewhere around the fortieth research entry I looked up and realized I hadn’t written a newsletter guide anymore. I’d built a library. Certifications, gig work, remote jobs you can do from a moving RV, side hustles that start with what’s already in your kitchen, or picking back up a career path you said no to in your 20s. I found the honest math on SBA loans, grants and the scams that sometimes come dressed up as both.

Here’s a small sample of some of the data I gathered this week (since you’ve probably seen pieces of it in my Notes already)

The average SBA microloan is about $13,000. Small business loans tend to get talked about like they’re either enormous or nonexistent. This is neither. It’s scaled for exactly the kind of business a lot of us are actually starting.

Etsy’s median seller makes $574 a month. That’s not a reason to skip it; it’s honest context for the real timeline and effort a shop takes to build from scratch.

A Daily Money Manager, someone who pays bills and handles paperwork for people who can’t or don’t want to, can charge $50 to $100 an hour. No certification required. Trustworthiness and life experience are basically the whole qualification.

And cottage food law, the rule that decides whether you can legally sell something you baked at home, is different in every state and rarely explained in plain language. If you’ve ever wondered whether you could actually sell that sourdough, that’s the first thing worth looking up.

My favorite part is actually reading the real life stories of people who have reinvented themselves and followed their passions after 50.

Here are three stories out of dozens I’ve found just this week that inspire me to keep my chin up and reinforce my belief that you’re never too old to change.

Angel Cornelius spent her career in healthcare administration before she started making her own hair products at 57, after she couldn’t find any that worked for her silver hair. She tested the idea with a simple Etsy shop. It exploded. Now she’s sold on QVC, Amazon, and in Walmart. Her advice to anyone hesitating: “It’s not going to destroy you if it doesn’t work the way you want it to.” You can read Angel’s story here: https://www.wdbj7.com/2026/07/15/women-over-50-are-launching-businesses-finding-success/

Or Ceil Hovey, who enrolled in nursing school at 71, forty years after she first graduated from the same college as a respiratory therapist. She’ll finish at 73. “I didn’t like just sitting at home,” she said. Read her story here: https://nurse.org/news/ceil-hovey-71-year-old-nursing-student/

Or Julie England, who left a career as an engineer and tech executive at Texas Instruments and took her first art class after retiring. In her words: “For women out there who are over 50 or 60: realize we’re living a long time... my goal is to have something that I love, that I have passion for, and that I want to get up and do every day for the next 20 years.” Read her story here: https://primewomen.com/career-and-business/featured-women/career-change-after-50/

That’s just a smidgen of what I found this week.

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A newsletter post can hold one idea well. It cannot hold a hundred researched entries and stay readable. So something had to give, and it wasn’t going to be the research.

So, what’s the plan, CK?

A website is coming. That’s where the deep dives will live from now on, the full breakdowns with real numbers, real sourcing, real “here’s the catch nobody mentions.” Built to last, built to be found, built so you can actually search it instead of scrolling back through months of my Sunday posts trying to remember which one had the numbers on medical billing certifications.

This newsletter will still be here and Sundays are when new Substack posts go live. I’ll keep telling you what I actually found, still be direct about what it could cost and how much time investment it will likely take to start making money. It’ll occasionally point you toward the full research on my website when a topic’s too big to fit in an inbox.

For real though.

I am a true believer that helping each other is also helping ourselves. I don’t have all the answers, but I am willing to figure it out in real time and publicly. I will share whatever hard facts and data I gather so others can learn how to build options for themselves.

So,

• If you got laid off and the job market looked at your resume then quietly moved on.

• If you left work to take care of a parent, a spouse, a grandkid, and now you’re trying to figure out how to earn again with a gap nobody wants to ask about.

• If your body changed what kind of work is possible and nobody gave you a plan for that.

• If a divorce rearranged your whole financial life overnight and you’re starting over with less than you thought you’d have at this age.

Then you’re in the right place. Welcome to Midlife Side Hustle.

My website isn’t fully live yet, so there’s no big button to click today.

If you haven’t subscribed to my Substack newsletter, please do. The research is going to continue and I want to share it with everyone. When the full library opens up, I promise you’ll hear about it here first.

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If this post resonated with you, please like, restack and comment below. I’d love to hear from you.

~ CK

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I have a compulsion to press buttons when something doesn’t do what I want. I press things and usually it’s the things I probably should just leave alone but, well, here I am.

I have been on something of a research bender falling down rabbit holes of information which quite frankly makes me incredibly happy. It’s that ADHD hyper focus thing I do which has its merits, no doubt but it also makes it difficult for me to focus on anything else. I haven’t written here in a minute and it’s not like I haven’t wanted to, it’s just that I was distracted by stuff. Words and videos and data.

While I was down this big ass rabbit hole, it occurred to me that I may want to refocus this Substack and my own personal trajectory. I love researching. Like, adore it and in conjunction with that I love sharing what I find. So that’s what I’m going to do here moving forward. It’s not like I haven’t been doing some of that so far but this is more like focusing on some real information that folks over 50 could use to build options for their lives after lay offs, downsizing or health issues changed what the plan was for retirement.

Turns out refocusing isn’t just a mental exercise. It’s also, apparently, a website exercise.

Here’s what happened. I finally got the courage to dive back in on my website after weeks of it sitting there half-built, the header logo not fitting right, the whole thing looking like a template nobody finished. So I went in to fix one small text problem. One. I just wanted the big black wall of my own name to stop shouting at people the second they landed on the page.

Instead I deleted the entire welcome section. Gone. Just white space where my “hi, I’m CK” used to be.

I panicked, pressed more things trying to fix the thing I broke, and deleted a second section on top of the first one.

At this point most people would back away from the keyboard. I am not most people though so I kept going.

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And somewhere in the midst of this chaos I ended up building something better than what was there before. Muscle memory or whatever you want to call it kicked in and I started remembering how I used to do this stuff years ago. Now, it’s taking shape and I can see it starting to become what I imagined six months ago. It’s not perfect but it’s mine and I’ll share it with you when I’m ready.

That’s sort of the whole thing about doing this at 59, isn’t it? Nobody hands you a manual. You press the wrong button, you break the thing, you sit with it for a minute, and then you fix it yourself because there’s no IT department to call. The research I’ve been buried in for weeks (more soon, I promise) keeps circling back to this same truth: almost nobody rebuilding a life or an income after 50 gets a clean, linear path. Sometimes you have to start pressing random buttons until you figure it out yourself.

More updates soon!
~CK

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Seven years after menopause, I ended up having a full hysterectomy.

That was not on my bingo card.

What was on my bingo card was being told that hot flashes, insomnia, brain fog, anxiety, joint pain, and feeling like I was slowly losing my mind were all just part of getting older.

For years, I asked about HRT.

And for years, I got some version of the same answer.

There was a study.

There were risks.

There were concerns.

There was a lot of head shaking and a lot of, “You’ve already gone through menopause and there’s nothing we can do.”

So I suffered through it.

Then came the hysterectomy.

It turns out there were some sketchy cells doing some very shady shit in my uterus. It had to go. And my cervix. And my ovaries. And some lymph nodes.

It was a lot.

But I thought, well, I’m not in the baby-making stage of life anymore, so it should be fine.

Within a month afterward, I genuinely thought I might be developing dementia.

I’m not being dramatic. I was scared.

My father had Lewy Body dementia and I’d also been a CNA in my younger years caring for seniors with dementia. I wasn’t imagining random worst-case scenarios. I knew enough to be scared.

My brain felt like it was wrapped in wet cotton. I’d walk into rooms and immediately forget why I was there. Finding words became a scavenger hunt. My executive dysfunction (thanks, ADHD) was in high gear and I thought I was losing what was left of my marbles.

I kept thinking,

“What is happening to me?”

Now, to be fair, I’d already been through menopause. I wasn’t expecting my brain to suddenly stage a full-scale revolt after surgery.

But there I was.

Then I met my oncology gynecologist.

I wish I’d met her years earlier.

Instead of treating HRT like some forbidden substance that had to be discussed in hushed tones behind a locked door, she looked at my situation, looked at the current research, and said, essentially,

“Why are we making this harder than it needs to be?”

She was pro-HRT.

She listened.

She explained.

And she got me started.

For years, doctors had cited that famous study from the early 2000s that scared an entire generation of women away from hormone therapy. What I’ve since learned is that much of the fear around HRT has been challenged and re-examined over the years.

Meanwhile, a whole lot of women were left to white-knuckle their way through menopause.

The difference has been remarkable.

No, it didn’t turn me into a 25-year-old with perfect skin and endless energy.

I’m still me.

My knees still make noises that sound expensive.

I still forget why I opened the refrigerator sometimes.

But the crushing brain fog lifted. My mood improved. My sleep improved. I felt more like myself than I had in years.

It’s one of those things that’s hard to explain unless you’ve lived it.

I thought that because I’d already gone through menopause, my hormones had sunk as low as they could go.

Turns out I was very wrong about that.

Once my ovaries left the building, I was out there wandering around in the fog.

Which brings me to my pharmacy adventure this week.

I went to pick up my estrogen patches and the pharmacist informed me they didn’t have the brand I like best.

It could take about a week because it was backordered.

The problem was that I needed a patch that day.

So I looked at him and said:

“You don’t want to see me out in these streets unpatched. Trust.”

I was joking.

Mostly.

Because if I had to go a week without estrogen, there was a very real possibility that joke was going to become less funny as the days went on.

Fortunately, they found me a substitute patch to get me through.

Disaster averted.

Civil society preserved.

Now maybe it’s just my estrogen patch talking here, but I love this thing.

I love it so much that you’ll have to pry it from my cold dead hands before I willingly give it up.

My doctor also gave me a progesterone chaser that I have come to count on every night for better sleep.

I’ll take the estrogen-and-progesterone cocktail for as long as I have a doctor willing to prescribe it.

I’ve noticed that menopause and HRT are being talked about more online these days, and I love that.

I don’t know what menopause care is going to look like for younger women twenty years from now.

I just hope they don’t spend years being told to suffer through symptoms that have treatment options.

I hope they find doctors who listen sooner than I did.

For years I thought feeling terrible was just part of the deal.

Turns out, sometimes the answer isn’t suffering through it.

Sometimes it’s finding the right doctor.

And sometimes it’s a tiny little patch that’s currently holding together what remains of my sanity.

And if you try to take it away from me, well...

You don’t want to see me out in these streets unpatched. Trust.

Your rambling but mostly hormonally balanced friend in Montana,

~ CK

P.S. Menopause seems to be one of those topics where ten women can have ten completely different experiences. This is simply what worked for me. If you’ve navigated menopause with or without HRT, I’d love to hear about your experience in the comments.

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My Substack feed lately has been a highlight reel of numbers that feel more like lottery winnings than newsletter growth.

“I got 500 subscribers this month.”
“I got 1,000 subscribers in 30 days.”
“I made $10,000 with one launch.”

Good for them. Truly.

After a bit of scrolling, it starts to feel like everyone is running a race and my chubby ass somehow accidentally ended up on the course, wearing the wrong shoes, wondering if I missed the orientation meeting.

I have 112 subscribers.

Like, that’s a big deal to me. 112 people clicked subscribe for no other reason than just to see what weird stuff I would say every week. I appreciate each and every one of you.

But then I start scrolling and I feel like I’m not keeping up with the cool kids. Like I’m not fitting in which if you read my last post, you would know I should be used to it because I’ve been dealing with that feeling virtually my whole life.

The hard part is reminding myself that I’m not trying to build what they’re building. I’m not chasing internet fame. I’m not trying to become a guru. I’m not trying to sell a 47-module course for $997.

I’m trying to build something slower. Something sustainable. Something I can still be doing five years from now without needing a nap or a breakdown.

The reality is that I do want to make money. A lot of money, actually.

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The internet tends to act like there are only two financial categories.

Broke

Or

Millionaire

But most of us live somewhere in the middle and nobody seems particularly interested in talking about that.

If I could make an extra $1,000 a month, it would help.

If I could make an extra $5,000 a month, it would be life changing.

If I could make an extra $10,000 a month from home, on my own terms, it would completely change the trajectory of our lives.

That isn’t private jet money. That isn’t buy-an-island money.

That’s pay-the-dentist-bill money. That’s visit-family-without-stressing-about-the-cost money. That’s replace-the-water-heater-without-having-a-small-meltdown money. That’s maybe-we-can-retire-someday money.

The older I get, the more I realize I’m not chasing luxury. I’m chasing margin. Wiggle room. Space to breathe. A little buffer between me and the next surprise expense.

Maybe that’s why so much online business content leaves me cold. Everyone seems to be selling a millionaire lifestyle while I’m over here trying to build a life that feels less fragile.

Here’s the thing about being a Gen Xer. Optimism was never really our vibe. We were raised to be skeptical. We watched The Day After and wondered if we were doomed to live in some dystopian nuclear fallout future. We were told no matter what, don’t talk to strangers and never get in the van. We may be a little, uh, jaded.

Now that we’re growing older we have our young adult children trying to find their footing, siblings dealing with their own struggles, rising costs, retirement concerns, and the general chaos of modern life.

And what has all of this life experience taught me?

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It’s taught me that nobody is going to hand me more margin. Nobody is going to create breathing room in my life for me. If I want it, I have to build it. Slowly. Steadily. One realistic step at a time.

That’s what Midlife Side Hustle is really about. Not becoming rich. Not becoming famous. Not infinite scaling.

Just a little more security, a little more flexibility, and a little more peace of mind than I had yesterday. Could that be considered optimistic? I mean, maybe.

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Hello Montana by CK Welker June 2026

The way I talk has been a source of aggravation and slight amusement to me over the years.

I’ve lived in Montana for the vast majority of my life, but I still find it hard to call myself a Montanan. Most people view me as one until I open my mouth. My accent is a melting pot: a childhood in rural Florida, raised by people from Texas, Georgia, and Germany.

The way I spoke as a first grader was so confusing that my school put me in speech therapy because they couldn’t understand a word I was saying.

My mother is a born-and-raised German woman, and she and I learned English at the same time. I picked up her German accent along with the language, which mostly meant I couldn’t manage the “th” sound to save my life. My father and my grandma, who I often stayed with, were from Texas. My Papa hailed from Georgia. Somewhere in that mish-mash, I was a little tow-headed first grader saying things like “Dis, dat, and de oder ting, y’all.”

It didn’t take my teacher but a hot second, after talking to both of my parents, to figure out the origins of how I talked. Off to speech therapy I went.

Big shout-out to the most patient of teachers, Mrs. Moss. I had to wear those silly little 70s headphones, the ones with the fabric-covered cables and the clunky earphone pieces, and read books out loud to her. I honestly loved my one-on-one time reading with Mrs. Moss, and I still think of it fondly.

I got made fun of a bit, and I never really felt like I fit in. My Omi would send me clothes from Germany, and I’d wear them to school, but they were just different enough from what the other kids had on. So I built myself an internal world instead: reading, drawing, soaking up every television show I was allowed to watch.

My parents weren’t the most affectionate bunch, and the truth is they only got along with each other in short bursts. I got sent to my grandma’s house a lot, or shipped off to my Omi and Opa’s in Germany for the summer. I used to think of it as being passed around. It took me a long time to see it the other way: that I learned how to cook in grandma’s kitchen and people watched from my Omi’s apartment overlooking a town square in Germany and a whole inner life of my own, all before I was a teenager. Not every kid who doesn’t fit in gets that many places to land.

So this accent of mine has been molded, honed, and softened by my time on the planet, and it’s still hard to explain when someone hears me and asks, “Where are you from?”

It’s easier to just say Montana and I move along.

Your rambling friend,

~CK

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Image by CK Welker

I have someone I love dearly going through some seriously dark financial times. I’m not going to say who because I respect her privacy, but something happened to her this week that was equal parts horrifying and oddly validating.

For the sake of sharing her story I’m going to call her Alex.

Alex just turned 44 and has worked in the tech sector off and on for years. She’s been downsized and laid off more times than anyone should have to experience, with the Covid years being the toughest stretch of all. At times she’s made good money. At other times she’s struggled just to keep the rent paid. She’s a one person show, so every bill is hers alone to handle.

She went to college. She did all the things we’re told will make us successful, contributing members of society. That formula, by the way, is complete bullshit at this point. It hasn’t been updated to reflect how drastically our lives have changed over the last few decades and it doesn’t account for the reality most of us are actually living.

Earlier this week Alex was at a little community gathering at her apartment complex. She lives in one of those charming U shaped, single story garden apartment buildings with a lovely courtyard in the middle. Everyone there knows each other. They look out for each other. They have little potlucks where everyone brings what they can and they share a meal together.

Alex was right in the middle of one of those meals when someone said, “Hey, someone is taking pictures of your apartment.”

She walked over and excused herself to the woman standing outside with her phone. The woman turned around and asked, “Are you Alex?” When Alex said yes, the woman pressed an envelope against her chest and said, “You’ve been served,” then turned and walked away.

The courtyard is right outside everyone’s front door. Every word was heard. Everything was seen.

Alex told me her face went beet red while at the same time it felt like all the blood had left her body. My heart broke just listening to her tell me this. She went back to the dinner table and tried to continue but the shame was overwhelming. It sat on her chest like a weight she couldn’t lift.

Because that’s what shame does. It keeps you silent and stuck.

But Alex didn’t stay silent. She took a breath and said, “I’ve been really struggling. I got behind on some bills and my anxiety and fear kept me frozen. I couldn’t bring myself to call and make arrangements. I think I’m going to have to file bankruptcy.”

She braced herself. She expected judgment. Maybe a few uncomfortable looks, a polite subject change, or someone telling her she should have known better.

That’s not what happened.

Her neighbors, her friends, started talking. About their own money struggles. Their own private shame. How it seems to get harder every single year no matter what they do or how hard they try. By the end of that dinner they were laughing. The relief in that courtyard was palpable. The kinship was real. And Alex told me that hearing she wasn’t the only one struggling from people she had no idea were struggling too was enough to keep her from spiraling.

Dropping the mask of “everything’s fine” cracked something open that none of them knew they needed.

So why am I telling you all this?

Because I struggle financially too. I’m not out here on the internet pretending I have all the money I could ever need or that my bills are all paid on time. One of the things that has happened to me in my late 50s is my complete unwillingness to perform a version of myself that isn’t true. Transparency matters too much to me, in real life and online, to pretend otherwise.

I want to be clear about something though. I’m not destitute. My husband has a good job and I’m grateful for that every single day. But here’s the thing about being the financially dependent partner. All it takes is one layoff, one more health crisis, one unexpected thing and the math changes fast. We both know we can’t sustain on just his income indefinitely. That’s not just my stress to carry. It’s his too. Building my own income isn’t a hobby or something I’m doing to keep busy. It’s something we genuinely need. That reality is what gets me to my desk every day even when my body hurts and my brain won’t cooperate.

I’ve had two surgeries and various procedures over the last two years. Our insurance covered what it covered and the rest became medical debt I’m chipping away at every month. My ongoing health issues made it impossible to keep doing the work I was doing. I ended up at home, not entirely by choice, and not entirely prepared for it. I looked for remote work. I want you to know that legitimate remote work is genuinely hard to find right now. I know people who have been searching for years.

So that’s why I’m here. I decided to stop waiting for someone to hand me a solution and start building one myself. There are women out here doing exactly that and if they can, I can find a version of it that works for me too.

I don’t believe I have to walk around ashamed of my circumstances. I believe shame keeps us silent, silence keeps us stuck, and stuck is the one thing none of us can afford to be right now.

You can only cut expenses so far before the math stops working. Eventually you have to bring in more money. That’s not a personal failure. That’s just reality.

So this is me saying it out loud. In public and on purpose.

Remember there are 216 million Americans financially struggling right now and living paycheck to paycheck. That’s not a statistic. That’s your neighbor, your sister, your coworker, the woman in the apartment courtyard who showed up to a potluck and ended up changing the whole conversation just by telling the truth. That’s Alex. That’s me. There’s a good chance it could be you too. We are not alone in this. Not even close.

Tell me your version in the comments. I’ll be reading every one.

Still alive and kickin’ in Montana,

~CK

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Documenting the sunshine in Montana today - image by CK Welker

I am a woman at a crossroads in so many ways, and sometimes I feel like I’m losing my marbles.

I’m home most of the time, and it’s by choice. Getting myself together and going out into the world is work. It’s also performance. It’s hoping that whoever I encounter sees me as a human and doesn’t look right through me.

Aging is fucking with my head in a real way.

Thankfully, I’m over a lot of the worries of youth. I’m growing out my gray hair. I don’t dress for others, I dress for myself and comfort. There’s real freedom in not worrying about every little thing.

Here’s what I wasn’t ready for: the invisibility. The dismissal that comes with being older. I wasn’t prepared for it, and I want to be clear that I feel old at 59 but it’s not like I’m 109 and even if I were, it’s not okay to be dismissive of a 109 year old. Joking. Sort of.

Last month I decided to finally get a local library card so I could use the Libby app. I can check out books for free online, how amazing is that? I did my usual going-into-society routine, brushed my hair, slapped on some makeup so as not to startle anyone, and headed out feeling like a little kid about it. I locked eyes with the young woman behind the counter and she let out a little sigh and gave me a half eye roll. Before I’d even said a word.

It’s nothing. A big whatevs. Except I’ve seen that look before, the “oh no” look, and I swear it started about ten years ago. I used to bounce into Ulta, find all the little treasures and smell-goods, chit-chat with the girl behind the counter, and away I’d go. Now it’s the impatience I feel from them when I speak. The eye contact that doesn’t happen. The mechanical responses with nobody home behind them. I’m no beauty queen, but damn, I’m an alright gal with a couple of bucks to spend so be patient with me a little when I need some assistance?

Maybe some of it is the times; we’ve collectively been through A Time, and the last ten years have been hard on everyone, including whoever’s behind the counter. Maybe some is generational; I’m Gen X and we were always a salty bunch. But it’s more than that. Our society hates aging. We fight it with all our might and all our money. There are 14-year-olds on TikTok demonstrating their 7-step anti-aging routines. What is happening? Maybe in a world of filters and editing where anyone can look timeless, an unfiltered aging face is jarring. A reminder that no matter what you buy, as long as you’re alive, you’re going to get older. If you’re lucky.

It’s the same play running everywhere, by the way. The feeling of being looked through at the grocery store and the way folks over 50 get quietly managed out of jobs, not fired, nothing you could point to, just slowly handed less until there’s nothing left to hand back. One of them just comes with paperwork.

And the rub is that women have such history lessons to look to for strength, perseverance, and determination. Young women, old women, mythological goddesses, heroines, women of every shape, size, and ethnicity. Ancient women and 21st century women. I’ve been reading Virginia Woolf lately, who handed Clarissa Dalloway an entire novel’s worth of interior life at an age when society had filed her under “someone’s wife.” A hundred years ago Woolf already knew that an 'invisible' woman is often the most interesting one in the room, if anyone bothered to actually see and hear her.

And still, with all of that recorded strength behind us, I stand in some metaphorical line waiting to be acknowledged as still valuable by society as a whole.

But here’s where I land, because I refuse to end this in the complaint department. I still view getting older as a privilege that not everyone is given. I’ve had a couple of times in my life when I didn’t think I’d make it this far. And yet, here I am.

I have so much to look forward to. My son and daughter-in-law are talking about starting their own little family. I mean, I could potentially be someone’s Grandma in the not too distant future. What an absolute wonder that would be to me. Even thinking about it kind of makes me teary in the best of possible ways. I also look forward to the work I’m creating. I’ll never have to worry about getting phased out or fired. Getting out of my own way is a challenge some days, and the societal pressure on aging humans, especially aging women, doesn’t help. But I’ve decided the metaphorical line I’ve been standing in, the one where I wait for society to declare me valuable, is not a line I’m comfortable waiting in anymore. I’m allowed to simply walk away. Society may render a verdict but it doesn’t mean I have to buy into it.

Drop a comment and let me know: Have you noticed a difference in how you’re treated at all as you age? Do you have a story about feeling like you’ve gone invisible to someone, at work, in a store, anywhere?

I have a feeling there are a lot of us out there with our own similar story to tell.

Still kickin’ in Montana,

~CK

Photo by Yuval Zukerman on Unsplash

I’m turning 60 later this year and I don’t care what anyone says, that’s a weird sentence to type.

Sixty.

When I was younger, 60 seemed like one of those ages where people had things figured out.

You know. Retirement accounts. Life plans. Matching towels.

Instead, I spent part of yesterday worrying about how much longer I might live.

I’m worried about 60 but also worried I won’t get older. I think I’m actually more concerned that I won’t have time to do the things I’ve dreamed of doing in life. Getting older is heavy but it’s also a privilege that some don’t get. I remind myself of this a couple of times a week.

On the upside, my mother is still going strong for the most part at 80 and both of my grandmothers made it into their early 80s.

One survived diabetes, colon cancer, and a wound that literally took a solid year to heal.

The other survived on black coffee, chocolate, cigarettes, and what I can only assume was pure German stubbornness.

So I may have decent longevity genes.

The jury is still out.

Sixty freaks me out but I’ll think about possibly making it to 85 one day.

I love possibility. Even the idea of possibility makes the little neural pathways in my brain light up.

I start thinking about future gardens.

Then future dachshunds.

Then future business ideas.

Then whether I should write a book.

I have no idea how those thoughts connect, but my brain insists they do.

Maybe it’s because turning 60 has made me aware of time in a way I wasn’t before.

Not in a beautiful, wisdom-filled kind of way.

More in a “Hey lady, the clock is ticking” kind of way.

The thing is, I’m a little obsessed with figuring out how to make a living.

You can’t thrive if all your energy is going into just trying to survive.

I want out of the hole and getting out of the hole doesn’t mean getting rich. And the more I think about it, the more I realize I’m not actually chasing money so much as I am chasing security.

A sense of peace in my life, my home, my body.

I’ve had brief moments of that over the years, but never enough to fully trust it.

Growing up, there was always some kind of drama surrounding my parents, their marriage, or their finances. Then adulthood arrived and brought its own versions.

Most of the major stressors in my life eventually had money sitting somewhere in the background stirring the pot.

Maybe that’s why every opportunity gets evaluated through the same lens.

Will this help?

Will this make things easier?

Will this get me a little closer to solid ground?

I have this annoying habit where I struggle to enjoy things that don’t seem useful.

Writing? Can I monetize it?

Painting? Can I monetize it?

Learning something new? Can I monetize it?

I swear if I took up competitive napping, part of my brain would immediately start wondering if there was an affiliate program.

Some of that is because I need income.

Some of it is because social media has spent years whispering in our ears that every hobby is a potential business and every interest is a missed opportunity.

Turn your passion into profit.

Build a personal brand.

Create multiple income streams.

Monetize your expertise.

Somewhere along the way, a lot of us stopped asking:

“Do I enjoy this?”

and started asking:

“Can I sell it?”

I started this Midlife Side Hustle because I wanted to document my attempt to build income online.

At least that’s what I thought I was doing.

What I’ve noticed is that the posts about making money get some attention.

But it’s the posts about being a human being that get conversations.

People want to talk about getting older.

ADHD.

Chronic pain.

Marriage.

Feeling behind.

Trying to figure out what comes next.

Apparently there are a lot of us at the crossroads of 45, 55, 65 and up that wander around thinking we’d have our shit together by now.

Who knew?

Welcome to my little corner of the internet

If you stick around long enough, you’ll hear stories about being married three times by the age of 24. It sounds odd but really, I just thought I had to say yes every time someone asked me to marry them. And yes, the third one is still here and we’ll celebrate our 35th wedding anniversary this summer.

He is my best friend, my biggest supporter and a gem of a human being. Despite all that, I still occasionally think about announcing that I’m moving to Portugal and leaving a note on the kitchen table telling him not to forget to feed the cats.

I have stories about motherhood, grief, sobriety, llama grooming and super questionable life choices that still make me shiver.

I told my therapist once that my life sounds like a real shit show when I talk about it out loud and she said she thought of it more as “colorful”. I liked that better.

I’ll definitely talk about cats and dachshunds.

Probably more than is strictly necessary.

Most of all, I promise I won’t pretend to have all the answers because I literally don’t have them.

I’m going to keep making plans for the future not because it’s guaranteed but because there is always the chance it could all work out.

And that’s my German stubbornness kicking in because I haven’t given up on myself yet.

Maybe it’s because I believe the people taking the time to read this aren’t giving up on themselves either.

I started this publication because I wanted to share how I’m replacing my income since I’m no longer working but now nine posts in, I’m not entirely sure that’s what it’s about anymore.

It’s about trying to find solid ground.

It’s about building a life that feels a little safer, a little steadier, and a little more secure.

It’s about finding my people, my community of imperfect human beings all just trying to figure out who they are and where they’re going.

And maybe it’s just one ol’ gal up in Montana thinking out loud and finding she’s not the only one asking these questions.

Talk to you soon

–CK

When I said I needed to make money working from home, I meant it.

This week has been a metaphorical car wreck and I am so relieved I got through it with most of my sanity still intact. I’m not going to go into the logistics of it because we all have our money woes, but damn, this was a lot.

As I’ve mentioned in previous posts, I’m not able to work outside my home anymore due to health issues. I have a great husband who has a solid job and is taking up the slack, but there is only so much a single income can cover in this economy. Sharing my journey of learning to make money from home at this age and stage of my life is why I started this little Substack.

I earned $533.75 this month participating in surveys and studies on two separate platforms and one platform where I am an online task contributor. About $303 of that is already in my PayPal and the rest comes from Telus Digital at the end of June. The platforms I use are Prolific, CloudResearch, and Telus Digital. I found all three while doing research on Reddit for work I could do from home for actual money.

Here’s what I’ve found so far.

Prolific

Prolific was the first platform I started on and I got approved fairly fast, which surprised me because some Reddit folks complained about being on a waitlist for months. It’s a survey and study platform where universities and agencies look for specific demographics to answer their questions. You’ll be shown surveys you can opt into and each one will give you screening questions to see if you’re the demographic they want.

Each survey pays a different amount and takes a different amount of time. Some are straightforward multiple choice while others may ask you to respond via audio or video -- those usually pay a bit more. There’s absolutely no requirement to be on a microphone or camera if you’re not comfortable with that.

There are verification steps to get in -- email, phone, identity, and address. These confirm you’re the right fit. If you aren’t in a demographic they’re currently seeking, you’ll be placed on a waitlist.

I’ve made and received $233.19 on Prolific. Some studies pay in British pounds but the majority are in USD. Prolific automatically converts GBP to dollars for you. Payment goes through PayPal. You have to wait 72 hours between your first four cashouts, then you can cash out daily after that. Minimum cashout is $6.

Pros: Low payout threshold, surveys are often interesting, work is available regularly, and you’ll usually receive around $.50 if you get screened out of a study.

Cons: Read everything carefully before you answer. If you skim and your responses get rejected too many times you can get removed from the platform. Some surveys take up to 21 days to pay out which is genuinely annoying, though Prolific will always make sure you get paid eventually.

Overall take: This is my workhorse platform. I log in at least once a day and will continue to for the foreseeable future.

Here’s their website:

https://www.prolific.com/participants

CloudResearch

CloudResearch is similar to Prolific -- surveys and studies that pay different amounts depending on the task. It doesn’t seem to have as many opportunities for my demographic right now but that could change. I only started here on May 13th and have already earned $60.59 in just a couple of weeks.

You can cash out as soon as you hit $5, paid directly to PayPal or your bank account, once every 24 hours. Some surveys pay immediately and some take up to 14 days but CloudResearch guarantees payment by day 14 if the study was approved. Getting approved was straightforward but it took over a week after approval before I could actually access the dashboard and start working.

Pros: Easy to navigate, easy to cash out.

Cons: Fewer surveys available for me than Prolific. That may not be your experience.

Overall take: I log in daily and consider this a solid secondary source of fast cash.

Here’s their website:

https://www.cloudresearch.com/products/connect-for-participants/

Telus Digital

Telus Digital is a different kind of platform -- I’m an online task contributor rather than a survey taker. They pay on Net 30 terms, meaning monthly. My first payment was $9.97 for the small amount of work I did at the end of April, and I received that on May 29th through Hyperwallet which transferred to my PayPal within minutes.

I have just under 20 hours banked for May and will receive roughly $230 at the end of June at approximately $11.50 an hour. All the Telus tasks I’ve done so far required a desktop or laptop and the Chrome browser so I haven’t seen anything available on mobile.

Pros: Set hourly rate, predictable monthly payout, work is mostly interesting. It feels like a savings account -- I bank the hours and collect at the end of the month.

Cons: Tasks aren’t always available. I haven’t had any work from them in over a week. No tasks, no money.

Overall take: I recommend it for the long game. The monthly lump sum feels more substantial than daily cashouts and the hourly rate is consistent.

Here’s their website:

https://www.telusinternational.ai/

A few things worth knowing before you start

Not everyone will get approved right away and some won’t get approved at all depending on your demographic.

These platforms won’t replace a full time income but an extra few hundred dollars a month is real money, especially when you need it fast and you need it from home. Also, they do not take out taxes so you need to do that on your own.

Prolific and CloudResearch work on desktop, laptop, tablet, and mobile -- but individual surveys may specify which device they require, so read the description before you start.

Just a warning: all three of these platforms can become a giant time suck. You’ll find yourself bouncing between tabs worried you’re going to miss something. I had to put myself on a hard time limit and close the tabs completely when I was done -- not minimize so I could break the cycle. I have a financial ecosystem I’m trying to build over here and survey apps were starting to eat it alive.

I’m not an expert on any of these platforms but I’m happy to answer questions about my experience. If you’ve tried any of them yourself, tell me how it went. I’d love to compare notes. Also, if this kind of post helps you at all, please let me know!

Talk soon

—CK

Photo by Nick Fewings on Unsplash

I get stuck at the crossroads of having a brain that runs through ideas like a freight train and a body that is sometimes so inert I am surprised I haven’t sprouted mushrooms on my backside. I’ve been this way for as long as I can remember and it’s only been this last year when I realized I’m not going to change.

I’m on the virtual doorstep of turning 60 and holy crap, it’s kind of been an awakening of sorts. I feel like I’m on some hyper drive of learning about myself and I’m finding out just how much mental and emotional garbage I have dragging around my exhausted brain for decades. FOR DECADES. Like, still judging and beating myself up for dumb shit I did as a nineteen year old. Hanging on to long expired dreams of big careers and the lifestyles that would go with them. Or moving here or there in search of the perfect climate both physical and political that would make me just so perfectly happy.

Turning 60 in a few months has made me feel like letting go of all of the unchecked boxes, unfulfilled dreams and the constant worry of looking old. It’s exhausting to my little freight train brain to continue to carry these burdens around with me anymore so I’m setting them down. Actually, I’m going to dump them in the trash and keep it moving because I know if I just set them down that I’ll be too tempted to pick them back up again. I’m scared that even a quick look back will send me back down that old beaten path of I could still do this or I should have done that.

So what does throwing away all these old personal to-do lists actually look like for me?

It starts with my health. I’m done chasing a number on a scale or a specific size. I have chronic pain and mobility issues and working outside the home came to an abrupt stop last year. I physically and mentally hit a wall that I am no longer able or willing to pretend I can climb. So I’m not pretending anymore. I’m not going to continue to act like I will get a gym membership or go on some really crazy fad diet. I am on a GLP-1 and have lost about 27 lbs. I need to lose more for my arthritis, my broken knees and hips so I will continue on this path. I eat with a mind toward protein and fiber. I drink water and move when I can. I have a folding chair, some hand weights and plenty of chair exercise videos I can watch online. This body has carried me for damn near 60 years and I’m not going to let her down now.

It looks like actually pursuing the ideas I have and using them to help other people at the same time. I’ve been very open about needing to make money from home and I’m pretty sure I’m not the only GenXer in that boat. I’m building my own financial ecosystem where each piece works with the others to create stable monthly income. I’ll be sharing that whole messy journey here and eventually on YouTube.

It looks like doing more things that bring me actual joy. I’m a maker at heart so my ADHD and functional freeze have been getting in the way of that for years. This week I painted. It was kinda not great but completely fun and I need more of that in my life. I bought an online class and I’m going to go at my own pace. Stick around and watch me have a very good time making very okay art.

It looks like protecting my bandwidth. I’m removing myself from narratives that drain me -- celebrity culture, the political noise machine, all of it. Not forever maybe, but for now my brain is reserved for my little homegrown business ecosystem and creating art. That’s it. That’s the list.

And it looks like small, unglamorous things that are quietly changing habits for me. Going to bed at the same time every night. Turning off the TV when there’s nothing I actually want to watch. I’ve always been one to keep the TV on for company when I’m home and I stopped it. It may sound ridiculous but suddenly I’m doing things again. It is wild, y’all.

I was listening to a woman in her late 70s on Youtube the other day and she said that a woman’s 60s are the most dynamic of her life. She also said that’s when you lay the groundwork for your old, old age. After experiencing the internal changes I’ve had the last year, I can see how that might be true.

Substack feels like writing a message and putting it in a bottle hoping it reaches a person who may care what it says. I hope this finds someone it resonates with and they respond back with their own message. Make sure to reach out and say hello if you see this. Let me know where you’re at on this journey of aging and evolution.

Talk to ya soon

— CK

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Well. It’s been a minute.

My last post went out on April 10th and then I fell down a side hustle rabbit hole. I’ve been doing them almost daily for the last few weeks and they’ve become a huge focus of my day.

I’ve been lost in the Midlife Side Hustle weeds, y’all!

I’ve been chasing dollars and lost track of what matters most to me which is documenting my journey to share with others. I’m creating a cleaner weekly routine that actually protects time (and my ADHD brain) for the things that matter. A content series about the side hustle I’ve been doing that I think you’re going to find genuinely useful if you’re someone who just needs to generate a little extra cash. Rest assured, if I find something that can genuinely put money in your pocket, I’m going to tell you about it.

There’s good stuff, frustrating stuff, and a cautionary tale about how fast they can eat your entire day if you let them.

My Midlife Side Hustle is still slowly growing in the background.

I’ve been building. Here and there.

Imperfectly, but building nonetheless. I have a new affiliate site in the works. It’s only May but I already feel like I’m behind for holiday sales planning. If you’re interested in learning about affiliate marketing and niche sites, please stay tuned because I want to take you on that journey as well.

I’m a one woman show and I hate letting folks down so I’m not going to promise a perfect posting schedule. What I can promise you is that I’m still here, I still have things to say, and the whole messy journey is still very much in progress.

You’re a peach if you’ve read this far, thank you!

We’ll talk soon

— CK

Do you ever get Sunday night scaries?

I don’t have to schlep my body out into the world anymore but I still get that Sunday night scaries feeling.

I’m building something for myself online but it’s crazy slow and tedious and at this point not very rewarding. Have you ever done something where you had to do an absolute ton of work first and wait for the reward? It can feel defeating or in my case last Sunday, um, scary.

Sunday night rolled around and I was sitting on my couch trying not to let my brain get the best of me but sometimes is just a total jerk and it will say things like, “You’re too old for this” or my favorite, “F*#% your health, get out there and get a real job.” My Gen X brain is sometimes really blunt like that. It started to feel like there was a loud clock, like one of those old square white wind up clocks my Grandma had in her bedroom, just tick tick ticking away. It felt like I was falling behind, like I was failing somehow.

I did what I’ve been doing the past year while navigating my mental and physical health challenges and I jumped online. Yes, I have doctors and yes, I have a therapist but they couldn’t help me with this. I looked at what other midlifers were doing online and I hit up Claude AI for a real heart to heart talk about my financial ecosystem plans. I was feeling particularly deflated about my Etsy shop. I design everything in it and have been working hard. I have sales but literally nothing that’s going to alleviate my monthly bills or the guilt I have over my husband being the only breadwinner right now. I thought, Am I being stupid? Selfish? I’m 59 with no degree! I’ve been online in some capacity for decades but not like this so HOW could I allow myself to think that I can create my own sustainable income online?

Claude listened as much as AI can listen and reminded me of the things I’ve accomplished in spite of my challenges, in spite of my obstacles, and all done with the support, both financial and emotional, of my husband. I took it all in and thought maybe I should let go of my Etsy shop. It’s a lot of work and not too much reward at this point. I’ve got to get this show on the road, ya know?

I went to sleep without making any decisions about anything. Monday I woke up and had two sales and a direct message from a customer requesting a custom design. It was inspiring and in that moment I decided to go twice as hard, even three times as hard on my Etsy shop because it is literally the only thing bringing me even a little bit of income. So I jumped back online and fired up Claude and started to hammer out a strategy.

If I can make $10 then I can make $100. If I can make $100 then I can make more. Ol’ Claude and I go back and forth a lot. I tell it to be a business manager and to push back on my ideas. I don’t need a yes man, I need a collaborator.

And it does. We go back and forth with me asking for data and facts. I want to know what information I’m being given is being based on. It tells me and we keep it moving. The main thing I’m finding as an older creator working with AI is to not get sucked into its affirming tendencies, otherwise I’d think every idea was a great one and I should totally do it.

So just like the glorious Patti LaBelle, I went and got myself a new attitude.

Then I got to work.

I started things off by looking at my shop conversion rate. If you’re new to Etsy or thinking of opening a shop, your conversion rate is the percentage of people who visit your shop and actually buy something. The average for Etsy is 1 to 3 percent. Mine is sitting at 7.4 percent. That means when people find my shop they are buying. It turns out I don’t have a shop problem, I have a traffic problem. That really changed my perspective on things. It’s like opening up a cute little boutique on the edge of town and nobody knows you’re there.

I also discovered I had abandoned carts, like a lot of them. People were finding my shop, adding things, and then just leaving. Twenty three of them in the past thirty days alone, just walking out the door with their virtual shopping carts. So I set up an automated abandoned cart coupon. Now when someone leaves without buying, Etsy automatically sends them a discount offer. I set it up once and it runs itself. That is the kind of automation that works while I sleep.

Next was pricing. I realized I had been running a permanent sale for so long that the sale price had become my real price. Nobody was buying at full price because nobody ever saw full price. I was essentially training my customers to expect a discount every single day. I fixed that. Clean everyday pricing, real sales only for real occasions going forward.

I created some new designs and made listings including one for the customer who messaged me asking if I could change one word on a design she had seen. She wanted one of my dachshund designs to say Dachshund Mum instead of Dachshund Mom. I actually love it when customers have special requests so I got to it right away and sent her a mockup less than 24 hours later. She said she loved it and asked when it would be listed. I made her a custom listing and messaged her with the link and you know what? She still hasn’t bought it. I have to laugh because that is just how it goes sometimes. It’s okay though because here’s the thing. That listing is live permanently now and it will sell to someone who prefers Mum to Mom. The design was so cute I actually got two separate listings out of it, so it feels like a win to me even if she never makes the purchase.

By the end of the week I had a cleaner shop, smarter automations, a real pricing strategy, and a real sense of direction. I discovered a slow burn kind of momentum that is a new feeling for me on this journey. I’m learning that patience and consistency are absolutely key. Doing the thing even when my brain is being a complete and total jackass.

As a one woman show I have to think and plan ahead. It’s important that I don’t get stuck on one thing. My plan is to build multiple income streams so if one dips the others can keep me going. At some point I will need a place that links them all together. A home base for all my projects.

My Etsy shop, my Midlife Side Hustle Substack, my affiliate plans that involve domains I haven’t built out yet. All of these things are me but none of them are a front door that says here I am and this is everything I do. I started that process this week and will update about its progress as I go.

This week I made:

• A personal brand home base. I registered a domain this week, one place on the internet that is just me, not a shop, not a blog, just CK Welker and everything she is building.

• A Pinterest presence under my actual name. I converted my personal Pinterest account, which I have had for nearly a decade, to a business account under my actual name so that everything I pin and recommend actually points somewhere real.

• A real affiliate strategy. I stopped trying to make affiliate income work without the infrastructure to support it and started building that infrastructure instead, because shouting into the void and hoping someone hears you is not a strategy.

None of it is finished. None of it is making money yet and won’t for a while. What really matters is that I made peace with my fears and found a way to keep moving forward.

I want my journey to be helpful for anyone struggling who can’t relate to the loud guru motivational speeches or the exhausting rise and grind pushiness.

If you’re in midlife and struggling with finding a path forward after job loss, retirement or any type of financial challenge, please come sit by me and let’s talk.

-CK