How I Struggle to Succeed

I’m still pretending.

Pressuring myself to do it all. To learn everything.

Three years ago, today, I published an article that called out this kind of behavior. Pushed back on the notion this is what we should expect.

For someone who was not well known it was well received. I hoped it might spur a change of outlook in others. If only it had for me.


Allow me to explain my mindset when I wrote this original piece.

In February of 2010, I was laid off from my first real job. The economy was in a nosedive and I had managed to survive two rounds of layoffs before my number was called.

I had only been there 18 months and just started to understand what it meant to work for someone. I had also got married four months before.

I was in shock. I felt like a loser. And after 24 hours of wallowing in self-pity, I looked into finding some freelance work to tide me over while searching for my next gig.

It took two months, exactly the length of severance pay, when I found a job ten minutes away with a higher salary. All-in-all, not too bad!

This second job lasted six months before I was laid off again. The entire marketing department let go. Fun factoid, the man who gave us the bad news is now the governor of Pennsylvania! I kid you not.

Laid off twice, in six months, lit a fire in me. I determined never to get caught in a position like that again. I was going to learn everything I could and become an immovable force.

If you know anything about the history of web development since late 2010 you know a lot has changed. I’m not even going to go into a list right now because nothing is the same.

I found work at a small, fast moving, agency nearby. They got every client they sought and we put out great work. Whatever the latest techniques were, I was learning them and putting them to use.

I worked so hard at it. I consumed every trend and idea around. I broadened my reach to the fringe. I didn’t want to be a loser again.

Again, this job only lasted 18 months. This time I was the one deciding I would be moving on. I had given everything I had at this company.

Unfortunately, it only took 18 months to become completely undone. I was burnt out. I was working 60–70 hour weeks and that didn’t include personal time I was dedicating to learning.

I learned so much, including a lot of things I would never want to experience again, and it was time to move on.

So, in early 2012, a little over a year before I wrote that article, I made a career move.

I had left a company that drained its employees. Long hours rewarded long hours.

I got out because it was unhealthy in just too many ways. I was happy to see others do the same.


My next stop, and still current employer, promoted a much healthier work environment. Meaning we produced great work without losing our souls.

It’s a small company with an even smaller design team. We wear a lot of hats. We want to do great work even when it’s not demanded of us.

And here is where I was at when I wrote that article. And where I am today, still. I still want to be an immovable force. I still want to be invaluable. I still want to be immune from feeling like a loser.

I still work hard. I could work longer hours than I do. There’s plenty to improve.

I don’t like to settle. Settling sucks. Settling leads to mediocrity.

And that has been my struggle for the last three years. While I enjoy the work I do I’m more fearful of letting myself down. So I push myself to learn something else. I look at others and think they have this edge that I do not. They’ve accomplished more than I could.

I know I’m good though. I could throw myself at any challenge and do well with it. I’m generally aware of what I don’t know and I throw myself at closing those gaps.

Focus is tough when all you see is gaps, though. They say if you chase two rabbits you’ll catch neither.

I struggle to be seen. I’m not adept at promoting myself. Or promoting myself at the right time, at least.

But I’m tired. I thought doing the work would be enough. It’s another gap.

I know others feel this too. This is why I wanted to share this follow up article. To explain my mindset today. How I got to be here. Success does not come overnight and it’s not easy.

I am not discouraged, however, and I want to encourage you as well. Don’t let that imposter syndrome rear its head. I know you work hard too and you should feel proud of your accomplishments.

It’s a long road of putting in the work, showing up, and sometimes feeling like a loser. You might get laid off a few times along the way. That’s ok too.


If you have any response, please share it! I hope this resonates with you. If it did, will you consider recommending it so it reaches others? Thank you!


If you want to read that older article, I believe it’s very relevant still.