Changing Careers at 40: When the Fire Burns Out


I knew what I wanted to be when I grew up since I was 3 years old. One of those people where it was clear right away. I wanted to be a writer. I wrote thousands of stories in my lifetime, constantly writing in study hall, at home, on vacation, at college, at grad school.

But along the way things change as they often do, and I have very strong opinions on the “safety net” or “way the world works” arguments, but those rants are for another time.

I wasn’t churning out fiction best sellers in my 20’s, but I figured out early on how to make money freelance writing by finding clients online all the way back in 2005 and good thing, too, because I was homeless in winter in the Midwest at the time.

Not quite that cold, but as anyone who has lived through many Midwest winters can tell you, not too far off.

Not Stephen King But I Was Writing

I mean I was also heading to grad school to pick up an MFA so I could teach at the college level, so I knew that making it right off the bat as a fiction writer was a long shot at best – and I was fine with that. If someone asked me what job I’d prefer more…I wouldn’t have been able to think of one.

I LOVED the fact I was making a living as a freelance writer and I loved the fact I could find work online. I was making living with words and doing so in a way that let me travel frequently. Or work for clients in California, Florida, and Texas while I was living in a cabin in Alaska.

In fact, one such client led to one of the best jobs I ever had, the one I took after grad school, putting aside teaching ambitions, to work two years in Austin Texas until the massive downturn of 2008 smashed me and led time becoming unemployed for the first time.

Some would say this was a compromise because I was writing less fiction – but we need to work. And even if it wasn’t my #1 favorite type of writing – it was writing.

And as stuff like laptops and Wi-Fi became way more common, I was able to do digital nomad well before this was a term, much less a widespread practice.

Since the only thing I loved as much or more than writing was travel, in many ways this was the dream job.

And for years I absolutely loved it.

Then at some point, things started changing.

The Job Satisfaction Shift Began

This started happening shortly after I was 30 and the early signs of something being off actually came so piecemeal that I didn’t even completely notice it at first.

Why did I start burning out? Honestly some of the reasons were directly related to the work, some were how life became a massive car wreck at the time, some were things that just happened beyond my control.

  • Maybe it was burning out from arguing with clients who always wanted an unreasonable amount of work for a small amount of pay
  • Maybe it was the normal wear and tear from years of 60-80 hour weeks
  • Maybe it was the self-employment taxes and the realizing I was never getting another tax return in spring
  • Maybe it was how cool the group I worked with at my first “real job” meant as a stop gap from freelancing were
  • Maybe it was getting stuck – hard to love travel & work when you stop moving and stop traveling (getting stuck in a place I didn’t particularly like didn’t help)
  • Maybe it was an inevitable side effect of a nearly 7 year depression that could arguably be called a 9 year depression
  • Maybe it’s because I didn’t figure out how to ramp up my wages early enough
  • Maybe it’s because I enjoyed blogging a lot more and was splitting my writing time in three directions for years
  • Maybe it’s because after years of being depressed and severely sick I’m healthy again and want to wander
  • Maybe the idea that what you wanted to do at 3 years old, 16 years old, and 20 years old will still be what you want to do at 30, 40, or 60 is actually a really stupid unsupported point of view for most of us
  • Or, LIKELY, it was a little bit of all of that. After all, people change.
Maybe it was this. Also “Burn Out” tag on Pixabay – clever!

Long story short, I started taking short stints with writing and IT jobs to earn money and to take breaks from freelancing because I just didn’t want to do it. That actually should have been a pretty clear sign to me that things were shifting.

Way more of my attention went from freelancing to building niche websites and making money online through web 2.0, my own sites, and those types of sites. I just enjoyed that writing way more, but it took me a while to learn how things worked and a lot of times I would pick up and get good at what I had to do right before huge buy-outs, policy changes, or Google shifts (Hello and Good-Bye eHow, Demand Media, Associated Content, Squidoo, HubPages, Web 2.0 in general, Panda & Penguin updates, Blogspot page rank, Amazon massive rate cuts #1, Amazon massive rate cuts #2) would force me to more or less start over.

Which was a ton of energy and a lot of struggling. Add in a consistent drain year to year in how much I could produce in a day for pure freelancing, or how much worse Guru.com and Elance.com got…yeah.

You couldn’t write a better script for me falling out of love with freelance writing than the combination of things that came together.

But I stuck with it, because for people who fight, pitch opportunities, and refuse to quit they will be rewarded. That’s what I was taught.

And it worked.

I applied for some remote writing jobs I would previously have assumed I was unqualified for, made a very good impression on Spencer Haws of Niche Pursuits, and although I ended up not getting the job in a very, very close competition where I was 2nd of 450 applicants, I stayed active in the community, did my thing, and eventually he hired me for freelance work.

This was a very solid paying gig with a cool boss who gave direct feedback, I was trained up to do things the way he wanted, and then I set to it. Not only was that a very good paying gig that I enjoyed immensely, but it also gave me some amazing clips since they weren’t ghostwritten and opened other doors.

I even sold my old site for just short of $40K using Motion Invest, the website brokerage he is a founding partner in.

These were short-term gigs so after a few months of each run the contract ended and I moved on back to general freelancing (though way more time is spent building my own sites)

This led to a couple of clients who read his blog that I ghostwrite for, and they pay premium rates because that’s all I’ll work for now.

So during a highly focused hour, which I can always get at least one or two of in a day, I make $75 an hour at my current rate. During even a semi-focused hour I can make $50 an hour. And my clients are very happy with my work.

And I hate freelance writing more than I ever have.

Woo boy.

Don’t get me wrong – when I write I bust my ass. My feelings about writing are my problem, and not my clients. They pay for great writing and I deliver. I also work as few hours as possible because while I can focus intensely for 1-4 hours a day…I don’t know that I can freelance any more than that anymore – and I’m not sure I can do that every single day for client writing.

Which means no $2,000 weeks for me – but enough to spend the overwhelming majority of my time on my own sites and projects while I more or less break even.

But here I am with the ability to make a huge per hour amount, and I don’t want to do it (very important note: the clients are great – this has NOTHING to do with the clients, they are awesome, this is 100% on me and my soul searching)…so where does this lead me?

I’m Successful, So Why Am I Miserable?

The story we get told as children seems to be the same, no matter how clear it is that the world has changed. Some of this might be survivor bias. Some of this is the fact you just can’t be on top of how the world works for brand new adults when you’ve been adulting for decades by the time your kids grow up.

Some of it goes back to the fact the world just changes so often times the advice you get, no matter how well intended, is obsolete or doesn’t apply to people in your position by the time you get old enough to use any of it.

By all accounts I’m successful…by my own job standards, not anyone else’s.

And yet I’m still miserable.

I feel you, buddy. I feel you.

The truth is that it’s time for me to either figure something else or walk away and to put it bluntly, I’m not in financial position to just walk away, I can’t force freelance myself long enough to build up the money to do so. It’s time for me to find something else to do in life.

Brand new career at 40. That’s…slightly terrifying.

Honestly, there is a part of me that’s irritated about being part of so many group projects where others depend on me, even ones I LOVE like our awesome gaming blog, Assorted Meeples, because I see the desperate need for seasonal work and what they’re paying right now…I’d housekeep in winter at a sky lodge for $20+ an hour and free housing.

Despite having always seen myself as someone who loved travel, wasn’t scared jumping without a safety net, ready to try something new at the drop of a hat, it’s a lot scarier now. Because of my illness it has been a long time since I’ve done that actively, and those muscles get rusty.

The risk-taking feels harder when you’re 41 instead of 28. Having faith things work out is harder when it’s been years since you’ve seen that proven (although admittedly that’s because it’s been years since I’ve been able to take enough risks to see that play out).

Add in the fact that my ability to mass produce quality freelance content for clients or content mills from a hotel room WAS my safety net and with that gone…how do I jump back out there the way I used to? The way I want to?

So Where Does That Leave Me?

Honestly, I don’t see myself freelance writing five years from now. For the first time in my life the thought of freelancing in the future is soul-crushing instead of soul-affirming and that’s just not a place where I want to be.

For now, I will do my few hours a week of premium freelancing, and considering how hot the job market is in certain sectors right now, I’m going to look at copywriting and remote work jobs in the area.

Yes, this is only a step removed from freelancing but in a structured environment with a steady paycheck and set amount of hours – it makes sense especially considering I’ve only done two job interviews the past 6 months, because they contacted me, and just missed out on a six figure job in both cases.

If I can make enough in two years to more or less retire from work, then I can find a way to hammer through.

Long-term I 100% believe the blogging will absolutely pay off. Making more niche sites like the one my brother and I created and eventually sold. We’ve done it before, and I have three different niche sites really showing signs of life outside of Assorted Meeples, which is doing some really cool stuff.

But that’s still two years off, in all likelihood.

And if the copywriting jobs end up being too close…well the starting wages for a lot of manual labor have shot up around here. Maybe a year at a dead end job I don’t care about (but don’t have to waste high mental energy on) will be enough to keep things floating on, save up, and turn all the freelancing into extra savings or investment, and then wear on me enough to make freelancing look better for just a little bit longer…

Maybe I take a spring seasonal work job anyway to get a break. It’s not like I can’t keep blogging elsewhere or come back and re-join Thursday night games once the season is over.

I have options. I just need to remember that I have options.

But long-term freelancing is not one of them.

The irony isn’t lost on me that I’ve FINALLY managed incredible per-hour rates as a writer…and just as I hit that success I hate the work that got me there. This isn’t a mid-life crisis, this isn’t just being tired and you’ll get over it. But why stay on sinking ship? There’s no per hour rate in the world that justifies not being happy.

You’re a different person at 40 than at 20. And living the dreams of a different person because that’s what you worked so long for is the ultimate sunk cost fallacy.

And I refuse to do it.

Get Excited About a New Future

Honestly even writing this post got me less anxious and more excited for what lies ahead. I can teach English online. I can still keep the premium freelance clients until they end the contracts. Hell, my old convenience store job is starting at $16 an hour right now (Thank You, Great Resignation).

The blogs will keep growing and eventually one will take off. In the meantime, everyone needs help everywhere. If there has ever been a better time in my life to show up to a job with no experience and say, “This looks interesting, train me up,” well I don’t know about it.

Be excited for what can be, not what’s anchoring you down now. The future is going to be different, and different is good.

She’s got the right idea for sure.

Never Too Late…

I’m a firm believer that it’s never too late, and especially at a relatively young age like 40 where you’ve had 20 years of adulthood and even the average hard living male has 35 years of adulthood left. Throwing in the towel that early or sticking out with a “dream job” that you envisioned before actually working…that just doesn’t make a lot of sense to me.

Sunk cost fallacy. I’m not losing 20 years of freelancing by quitting. I still have those skills, those stories, and hey, five years from now who knows how I’ll feel about it? It’s not like I can’t go back – especially with the connections and history of quality work I have behind me now.

I’m not losing 20 years. I’m gaining the 20-40 I still have ahead of me. And gaining decades of life on my terms…that’s a steal no matter what the price!

I have no idea what the next steps will be, but I’ll be here to let you know every step of the way!

Shane Dayton

Writer, gamer, outdoor enthusiast, adventurer, and depression survivor tired of all the ugliness. Doing my best to live a life worth living, having fun, creating stories, and hopefully doing my part to leave the world a touch better than what I found it. Hope you enjoy the site and find something entertaining, helpful, or useful that's your kind of jam.

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