I Succeeded So Why Am I Depressed?

Shane Dayton
7 min readJun 9, 2021

Depression from success was something I’d heard about plenty. I’ve ready self-help/self-improvement, was (and still am) a fan of The Four Hour Work Week by Timothy Ferriss when it first came out, and remember him mentioning this multiple times as a legitimate problem when people “made it.”

To be honest at the time that sounded completely insane to me.

How could you succeed and then be depressed? How could accomplishing great goals not fulfill you and give you the extra boost of strength, energy, and encouragement you were looking for?

Photo by Paola Chaaya on Unsplash — This photo screams “adrift” to me, which is what it felt like.

How would removing the stress of building such a project over years not have a positive effect on yourself?

How would cashing in on a big pay-off not result in a really upbeat and joyous when you suddenly had the ability to live life on your own terms? Or simply not be stressed out every single time you ran the debit card at the grocery store?

And yet in the fall of 2020 a day came that I simply wasn’t expecting. The outdoor website my brother and I had built from scratch over six years of writing, SEO, and just sharing a passion for the outdoors received a big five figure offer we didn’t feel like we could refuse.

So we sold the site, and split it 50/50, a HUGE boon for both of us in a year that felt like a dumpster fire for most all of us.

Just Like That — I Thought Things Were Different

I kept looking at the bank account in disbelief. Even during my best years of work and freelancing I never had remotely that much money in the bank at one time.

Yeah, it wasn’t even close to retirement money, but suddenly so much stress and panic was gone.

The serious dental surgery I’d needed for years but didn’t have the money for? Covered.

The ability to take a few months off to try to work through six years of freelancing burnout? No problem.

Rent for the next year? Covered.

Startup money for the next big project whenever I wanted to do that? Still there.

Money to pay off all the credit cards? No worries at all.

Grocery shopping? Never had to check the accounts before hand. I knew the money was there.

Celebratory dinner post-site sale from a great BBQ Restaurant. Not pictured: 5 lbs meat, 20 tubs of sauce, and 3 lbs of the best cornbread & sweet butter you can find this far north.

The list of things personally important to me were suddenly no issue. Funds for a new tattoo? Check. Funds for a long overdue vacation? Check. Max out the IRA? Done and done!

And at first it was more amazing than I could have imagined.

If you’ve lived most of your life in financial duress, you don’t know what “normal” is. You carry so much stress every moment of every day that it colors, hurts, and haunts every single thing you do.

When that stress is suddenly lifted — it’s nothing short of an almost religious experience.

And Then…

There was a bit of an unease. Something wasn’t quite right. In between a few games of Stardew Valley for much needed recovery time, working on two novels that I’d put aside for far too long, and adjusting to post-dental surgery life, something just felt off.

At first I was terrified, because it was the same type of unexplained unease that I felt before my severe six year depressive episode that almost ended in suicide, but somehow by the grace of God and friends and severe stubbornness and pure dumb luck didn’t.

The feeling continued to grow and I realized that after the initial euphoria wore off, I wasn’t happy. In fact I felt really lost, and couldn’t understand it.

Money wasn’t an issue. I’d dropped over 70 lbs from working out and dieting carefully during the pandemic, I was still genuinely excited about what the future could hold.

But an emotional dread had settled in, and that was really surprising to me.

And that led to some serious searching and a deep dive. Not sure how many “answers” I found, but sometimes even the search just puts you in a better place.

Working Through the Post-Success Depression

If I personally knew all the authors whose “the sale won’t bring happiness” advice I called bull plop for years I would call and apologize. They were right. Somehow.

While I can’t add much to what’s already been written on the topic, I can share my personal insights:

It’s Okay to Be Conflicted

Few things in life are clean. There were tons of ups and downs with that website over the years and as much of a blessing as the pay-off was, that also suddenly removed a huge chunk of my time/purpose.

I went from working with my brother on a site every single day to…to nothing. And that is naturally going to cause some internal conflict.

You’re celebrating the victory you’ve achieved. You’re also closing the chapter on that project you poured so much of your life into, meaning you’re closing the chapter on that part of your life.

That comes with excitement about what comes next. And with sadness that you must recognized what has passed.

That’s normal. Realizing that made a world of difference in helping me work through it.

I celebrated not only the possibility of what was next, but let myself be sad over what had passed. And at that point the unease started to lift.

Be Prepared for the “Losing Purpose” Hit

This comes post-euphoria and in retrospect makes sense. Why do retirees need to keep busy? Why do entrepreneurs jump back into business after selling their first company? Why do actors/directors keep doing what they do into their 70s, 80s, or even 90s?

Having something passionate to work towards matters. I spent so much time working on the site for the big pay-off. When that pay-off came, I wasn’t ready to jump into my next project.

For anyone who might find themselves in a similar spot, think of something to eventually jump to.

That doesn’t mean you need to jump right away. Taking September and October off were crucial. I started burning out on the freelance writing for clients back in 2010 — which means I’ve been burning out on my job for 11 years.

The break was needed. But if I had a specific project in mind ahead of time to jump to when I was ready, a LOT of that unease could have been avoided.

Figure Out What’s Next

To some extent I had some ideas on this.

From the pure needs standpoint: I knew I needed rest from burnout and time to think. I needed dental surgery. I needed to lose weight.

Beyond that my brother and I loved writing about what we enjoyed, and we see the potential. So we started a couple really niche sites and each started another site based on hobbies or interests.

I also knew that I really wanted a creative endeavor like getting back to my fiction writing and I wanted to go more all-in with the gaming group I was with.

So the point was, I had options. They were far from filling in the full picture but there were things I could start exploring once the energy returned.

Clean House

This might be literal if you’re not great with avoiding clutter (guilty as charged) but it’s also a good time to take care of the internal stuff. Try out online therapy, journal like crazy to get all those internal thoughts out.

If you’re majorly overweight, use your free time to exercise and get into better health. Take care of things like new classes. Look up those online classes for hobbies you’re interested in.

Work past anything you need to work past. Even little victories here will make you feel great about other things that are happening.

Learn (or Re-Learn) How to Dream

I used to be a huge dreamer. For a long time that hasn’t been the case. Even post-depression, that was a part of me that’s struggled to come back.

Many of us limit our dreams based on circumstances. Terrible circumstances or stretch of life, and the dreams and creativity shrinks to make way for survival mode.

When you can get out of survival mode for even a little bit, it’s amazing the ideas, thoughts, and solutions that pour in. But this doesn’t happen naturally. At least it didn’t for me.

Spend some time allowing the mind to wander, daydream, think “What if?” It’s well worth it.

So the Lesson Is You Get Full Fulfilment By…

I really wish I had an answer to this. I’m going to buck so many self-help gurus and tell you the truth:

I don’t know.

I know, super helpful.

But considering how personal each person’s mini-existential crisis is, news (sarcasm).

And let me be clear. Selling the website was 100% the right move. The dental surgery and follow up health benefits have been life changing.

So What’s Next?

Hard to say. I spent a burst of energy from productive months post surgery creating some new niche sites, and I’m putting together a personal site where I can just write whatever. Because for me personally I need that creative outlet.

I’m happy to say I’m up past 120 pages on both novels, although still working on that consistency thing.

The most important part: my mini existential crisis didn’t explode into full-blown depression.

I was surprised how quickly the glee of a major victory, the joy from a big pay-off, ended up transforming into feeling empty, drifting, and rudderless. Fortunately, I had the time, tools, and enough happening to work through it.

I hope my personal experience here has helped, and if you find yourself looking at a “life-changing” moment be prepared so you’re not surprised by a “Wait a minute, why do I feel empty now?” moment like I was.

Thanks for reading!



Shane Dayton

Writer, gamer, passionate traveler, I'm at my happiest when I can spend my time where my interests meet. Hope you enjoy and thanks for reading!