How to Avoid Side Hustle Burn Out (My Personal Horror Story)

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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I said it would never be me. I’d never succumb to side hustle burn out.

I know how to handle stress. I’m capable. I made it through college on barely any sleep.

Surely, I’d be able to manage a full-time job, my four children’s needs, a healthy relationship with my wife, a solid workout routine, time with friends, good sleep habits AND a thriving side hustle.

Turns out I was participating in what I’ve now come to know as “magical thinking.” In other words, I was headed straight for overwhelm, exhaustion and having to step away from something I spent nearly 2 years trying to build.

The Current State of Burn Out

Apparently, my experience is not unique. There’s been what seems to be a global pandemic of burn out over the last few years.

A study by Yerbo found that 2 out 5 tech workers are experiencing burn out in some shape or form. That puts this modern phenomena squarely into the realm of other commonly shared experiences like disdain for traffic and millennial’s bafflement over an entire generation now embracing crew socks.

But, here’s the thing, what’s been talked about has had mostly to do with people’s FULL-TIME job. Little has been mentioned about side hustle burn out.

We find ourselves in the age of the “overemployed.” You’ve heard about this right?

There’s a whole sub-sect of people who have figured out a way to have multiple full-time jobs at different companies all without any employer knowing of the overemployed employee’s moonlighting.

In case you’re wondering if this is a small group of people who have somewhat superhuman abilities just know the “Overemployed Subreddit” has 300,000+ members.

The volatility of jobs in the corporate world has forced everyone to think differently about where they get their paychecks from.

We’re treating work less like a committed relationship and more like an investment portfolio. AKA, “I’m just looking for a good time. Nothing long term, please. Now where’s my paycheck?”

But, that has its costs. Something I found out personally.

My Journey into Side Hustle Burn Out

A few years ago, I was holed up in our extra bedroom working feverishly on a client’s project that HAD TO BE DONE before Monday the following week.

My family was off with some friends celebrating some holiday that I can’t even remember because of the sheer amount of stress I was feeling.

I was frustrated. I was kicking myself for even saying yes to this project and I was done.

For a lot of years, having a side hustle wasn’t an option. I was a single dad and I had to make extra money because my job as a worship pastor wasn’t cutting it.

But, that wasn’t the case anymore. I was finally at a point in my life when all the skills I’d struggled for so long to build had put me in a place financially to not have to work crazy amounts just to make it.

But, for some reason it didn’t feel that way.

Side Hustle PTSD

It turns out this isn’t unique to my own experience.

In their book, “Burnout: The Secret to Unlocking the Stress Cycle” Emily and Amelia Nagoski talk about how any time you encounter something that causes stress there are actually two parts to it.

There’s the “stressor” or the thing causing the stress. But also this cycle that starts in your body when you encounter that stressor.

And, typically that cycle doesn’t end even when you’ve handled or taken care of the stressor.

So, for instance, you might feel super overwhelmed from having too much work to do and not enough time to do it.

But, let’s say you pull through stay up late and get everything done in the time you needed to get it done.

Great! That takes care of the stressor BUT you’re body will still feel the stress from being overworked until the stress cycle is complete.

I heard Chris Hemsworth say something similar in the documentary Limitless.

He was talking about how in the early years of his career, he was couch surfing while going to hundreds of auditions a week just to try to find something.

Then he landed the role of Thor and he no longer had to hustle as much to make money. But, even though his brain knew he was in a better place, he instinctively kept feeling like all of it could end and he might not ever get another role.

That was me…just without all the muscles and fame.

I still worked like that single dad who was worried if he didn’t land another project he might not be able to buy groceries for his kids.

Even though I had dealt with the “stressor” of not making enough money, I hadn’t dealt processed all the stress I’d experienced through one of the toughest seasons of my life.

So, I pulled the plug. I made that my last project. I shut down the Self-Made Web Designer blog, podcast and youtube channel.

My Come Back from Side Hustle Burn Out

I told myself and everyone else I was taking a 2 month break. But, 2 months turn into 3 months…turned into 1 year and pretty soon I realized I need more than a break. I needed full on recovery from side hustle burn out.

In the process of recovery, I learned so much about what it means to handle both the stressors AND the stress of life. And, I learned a few ways to handle high stress seasons without shoving all my emotions down and trying to avoid them.

The process was painful and longer than I would have hoped BUT it’s something I think might be able to help someone who’s going through something similar.

So, I’m glad to have gone through the journey. Here’s what I came back with.

See if There’s A Thing Behind The Thing

In my own journey there was a thing behind the thing.

The “thing” was building a great business. But, the thing behind the thing was me trying to prove myself and probably even more so avoiding pain by overworking.

I get a sense that the same might be true for a lot of other folks out there. They don’t want to just build a great business or make more money or whatever.

There’s emotional baggage attached to their “why.”

The thing about starting any kind of goal that’s rooted in emotional trauma is it ends up causing more grief AND it’s nearly impossible to sustain.

You’ll never be satisfied no matter how much success you achieve if that’s your motivation. That kind of problem can never be solved from achieving your goals.

It reminds me of what Socrates wrote about people who were trying to solve their troubles through traveling:

“The reason which set you wandering is ever at your heels. What pleasure is there in seeing new lands? Or in surveying cities and spots of interest? All your bustle is useless. Do you ask why such flight does not help you? It is because you flee along with yourself.”


So, my encouragement to help you avoid side hustle burn out is try and see if there is some unmet need in your heart that could never be satisfied from what you’re trying to accomplish.

Maybe there’s not which is great! But, if there is, it’s time to figure some things out.

It doesn’t necessarily mean you have to stop doing what you’re doing like I did. But, it definitely means you need to do some inner work.

And, at the very least don’t expect the thing you’re building to solve problems that have deeper roots.

Most often, if you’re sad now, building the business, losing the weight, landing the job won’t do much to change that.

Fight to Stay Authentic

There’s something about hitting the record button when I’m making videos or podcasts that makes me feel like I’ve got to go into performance mode. My wife and kids call it my radio voice.

The problem with that is if I’m not careful I start to lose my authenticity. And, when I don’t feel authentic it gets really easy to lose site of the ultimate purpose I started Self-Made Web Designer in the first place.

That was another piece of the puzzle for me on the road to my own personal burn out.

The Yerbo study cited “depersonalization” as one of the biggest reasons why you might end up facing side hustle burn out yourself.

Depersonalization is where you feel like instead of living in your body you’re almost outside of it watching your life pass in front of you like a movie.

The reason we get there is because we feel like we’ve got shut off our feelings to get done what needs to get done.

I was creating so many videos in such little time that I didn’t have time to slow down and ask myself, “is this who I really am.”

Now, what I’m doing and what I encourage you to do is figure out a way to stay present and authentic no matter what.

Set really clear boundaries with what you’re willing to do and what YOU’RE NOT willing to do and stick to it.

If by being more authentic I don’t get as many views, so be it. If by being more authentic I don’t make as many sales, so be it.

I’d rather fail striving toward authenticity than succeed by being someone I’m not.

You do the same.

Don’t say “yes” to a client demand you’re not comfortable with just to get the project.

Stand strong in your convictions and even create a list of nonnegotiables that you come back to every so often to remind yourself.

Change Your Expectations

According to Emily and Amelia Nagoski, we all have this inner “monitor” that is constantly evaluating whether or not the effort we’re putting into achieving something matches the progress we think we should be making.

We start to perceive the work we’re doing as burdensome if the balance between effort and progress ever gets out of whack. Do that long enough and you will quickly reach side hustle burn out.

Makes sense right?

There was a pretty popular study they did at Harvard that showed the same thing. They found:

“Through exhaustive analysis of diaries kept by knowledge workers, we discovered the progress principle: Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work.”

Even if something is super hard or takes a lot of effort, you still feel like it’s worth it if you feel like you’re making good progress.

But, once that progress reaches a point that you feel is too slow, everything shifts and finds yourself frustrated.

The Frustration Solution

So, what do you do?

Well, you could try to figure out ways to overcome the things holding your progress down. But, I’m guessing if you’re reaching the point of frustration you’ve probably already tried a few different ways to make that happen.

Another option is to change your expectations.

You either need to embrace the pain and difficulty for what it is OR you need to redefine what a win looks like.

During my sabbatical I ended up signing up for a half ironman. I know. I was supposed to be processing my emotional trauma but instead I participated in one of the hardest races out there.

But, it taught me something. I was able to cope with the pain more when I just accepted the fact that what I was doing was going to suck.

So often, people spend TONS of energy trying to make things that are going to be hard not feel hard. Which in turn just makes it harder leaving you frustrated.

Another thing you can do is find smaller wins a long the way to the bigger win.

So, in my half ironman race I would tell myself, “just make it one more mile.” I did that enough (70.3 miles to be exact) and I was crossing the finish line.

If you’re doing anything that’s worth the effort it’s probably going to take longer than a few days. So, be sure to set up wins a long the way that you can celebrate so you don’t find yourself in the middle of side hustle burn out.

Don’t Let Cynicism Win

I am not naturally positive.

It actually takes a ton of effort for me to be grateful even though you’d never know it. I don’t walk around like Eeyore from Winnie the Pooh.

But, my inner monologue is very different.

In fact, some times it takes other people telling me that what I’m doing is actually going really well for me to even realize it.

It turns out this emotional disposition is one that is primed to lead to side hustle burn out. In fact, the more overwhelmed and burned out you become the more cynical you are.

You find it impossible to see the upside of what you’re doing. Like even if EVERYTHING WENT RIGHT you’d still have a hard time being excited about it.

There are two things I found to be important if you find yourself in a similar situation.

First, you have to do a little preemptive work to keep yourself from getting to the point of no return.

Make sure you’re taking some time before every work session to remember why you’re doing what you’re doing. Keep records of people you’ve helped.

I have a folder on my computer of screenshots where people were impacted by what I do.

Ali Abdaal talks about how when he went from a part-time to a full-time YouTuber he actually hated it. What was once done just for fun was now an obligation he didn’t like keeping.

So, to pull himself out of it, he would read an affirmation he’d written before recording every video.

It helped him find his spark again.

BUT, it might be time to ask a friend to help you with perspective if you’re past the point of being able to find things you’re grateful for with what you’re working on.

The person that does for me is my wife.

She’s been the voice of reason when I’ve been on the edge. She’s even told me when it was time to step away AND the one who encouraged me when it was time to go back.

I know for sure I would not have processed my own side hustle burn out if it weren’t for her.

It’s so important to have people to walk the journey with you. Find someone who’s willing to stand by you even if it’s not a spouse.

It could be someone that’s trying to do something similar to you. Find a community of people that are building the side hustle you are and help them out when they’re struggling.

We were made to do life with others. If that’s not a part of your equation, it won’t be long before you find yourself fed up and exhausted like I was.

Wrapping Up On Side Hustle Burn Out

If you made it this far, kudos. You must be really struggling.

I feel you friend.

I felt so much pain when I walked away from the Self-Made Web Designer. It was like losing a pet.

Something I had poured hours of time, energy and emotion into now had the potential to go quietly in the night.

But, hopefully, my story can be an encouragement to you.

If you find yourself in a similar season, it’s okay. It’s never too late. You’ve got time.

But, while you’re waiting make sure you’re doing some solid inner work AND make sure that when you do come back to it you’ve got some solid nonnegotiables in place.

Some times life is like the running leg of a half ironman. Every move is painful and you want to give up. But, if you just keep taking one step and then another, you’ll find yourself crossing the finish line with everyone cheering you on.

Well, maybe not everyone. But, I sure will be.

lit match burning out to represent side hustle burn out


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



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