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No-nonsense perspectives on startup growth

This article was published on April 19, 2021


I used to be great at my job… then I founded a startup

You're not a good employee anymore.

I used to be great at my job… then I founded a startup
Benjamin Webster
Story by

Benjamin Webster

Co-Founder, Troopl

Benjamin is a learning development expert who has led programs at Tesla, Apple, Microsoft, and BlackBerry. Benjamin is a learning development expert who has led programs at Tesla, Apple, Microsoft, and BlackBerry.

Usually, I’d hit my groove in a job when I was about 6 months in. At that point, all the little things that had confused me at first started making sense and my performance started to reflect that. But during the whirlwind last 6 months of launching my own startup with another first-timer — I’ve realized I’ll never experience that again.

So herein lies the memoir of a relatively new founder (or flounder?), which will explain why you’ll never be ‘great at your job‘ again after starting your own company.

Sweet safety of being given goals

I used to be great at my job. I solved problems. I got shit done. I did more than what was expected of me. At a relatively young age, I touched down in Europe with what I considered to be my dream job.

My job description was flexible, and as I moved across the continent, I knew what I had to do when I touched down in each of the markets, from Norway to Portugal, the UK to Israel. And I got it done reliably. 

Within 6 months of that job, I was getting really good at what I did. People started coming to me to solve their local challenges in a way that made me feel like they only trusted me to fix them. I was the oddball in my team, but I quickly became known as the multi-use jack-of-all-trades (master of only a couple). 

I brought with me an entrepreneurial attitude to the work I did in my team. I built quickly, iterated often, constantly questioned focus, strategy, and priority to ensure the best work was being devoted where it needed to be. 

I was presented with problems, I solved them, and my superiors were happy.

Needing a bigger challenge

After doing that for a few years, I felt as though I was somehow treading water. Personally, I wasn’t developing at the pace I set for myself, and my projects were getting cycled through the business so quickly that I felt the opportunity to build momentum had completely vanished. 

So I bailed. I joined a good friend full-time on a startup. Our first foray into business ownership, tech platforms, software sales, content creation, you name it. It was all new.

We were green… and still are. 

Building a business from the ground up meant everything changed. My ‘jack-of-all-trades’ skillsets suddenly accounted for nothing — because I suddenly had to take everything from A to Z on my own.

I anticipated this to a large degree and flooded my bookshelf with the kinds of wisdom I knew I would need. My bookshelf is still totally out of control, but I’m getting through it.

I started building relationships with people who I knew I could learn from. I saw this change in many ways as going back to school. It turned out I was right. But I forgot how brutal school can be. 

What makes me a good employee now?

As I got more settled in my new role as founder, I realized the common metrics I was chasing down before didn’t mean shit anymore — especially the ones I used to determine if I was ‘great at my job.’ In the startup world, there is an endless sea of tasks to do, people to talk to, and things to learn. It still overwhelms me frequently.

Without colleagues or superiors, it can be incredibly difficult to know where to focus your attention at times. What makes this particular task more important than the other? Who decides if you’re ‘great’ at your job?

I had to get comfortable with multitasking on a level I didn’t quite know how to handle at first. The biggest challenge has been focusing on a supremely small, extremely important set of tasks, and protecting the time you need to get it done.

This includes the time you need for yourself to eat, sleep, relax, do things you love, and be around the people dear to you. Don’t skimp on this.

So if you’re planning on jumping from a corporate monster into your own startup. Absolutely do it. Or don’t. It’s impossible for anyone to tell you if you’ll love it, hate it, or anything in between.

But if you do make the jump, be prepared to kiss being a good employee goodbye — those days are officially gone.

Instead, you’re finally just… you.

So whether my startup journey turns out to be a raging success or an embarrassing flop that takes me straight into the therapist’s chair, I wouldn’t change this experience for anything.

I’m having fun, I’m challenging myself, I’m finding my feet in a sea of toes that I try not to step on too often. I’m finding more and more ways to do what I’m great at as time goes by. I’m no longer a good employee, but I’m finally me.

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