Celebrating 10 Years of Startup Adventures

Adam Oskwarek
5 min readAug 25, 2021

Well, that’s a little inaccurate. It’s about eleven and a half years. I’m considering this a slightly delayed celebration, due to you-know-what. Over a decade of change since I started on my adventure by founding a company. It was a marketplace. No, not the easiest place to start. Since then every year has been exploration, discovery, refinement and most of all learning.

I didn’t leave the safety of big companies for a couple years after that initial foray into entrepreneurship (whatever that is!?!?), but the adventure had officially begun. Everything that has happened since has been growth — cumulative and additive. Broad and deep. Each year presenting both new opportunities as well as new things to explore and figure out. In some ways it’s been a bit relentless, though I certainly wouldn’t change it, even if I was able to.

So much for us who work in startups, scale-ups or building things from scratch is about being intrinsically internally motivated. To have the confidence or drive to make a hypothesis, who it could be for, figure out how to do make for them, to try, to learn and adapt when necessary.

This is an article inspired by a lovely coffee I had with a friend recently who inspired me by talking so openly and positively about their perception of me, my experience, my contributions as well as my mindset.

After a fairly tough couple of years (I think most of us will agree!) it put a nice bounce in my step. For those of us who have worked in or on building new tech, or companies, or teams, it can be like running after an always shifting or unreachable goal. A vacuum of never ending next things to learn, figure out and do. So much so that when you unexpectedly receive external validation or praise it really hits home.

Having spent chunks of time reflecting myself over the last year or so, it was amazing to see some of the same hopeful and positive conclusions I’d reached reflected back. I spent two days letting the kind words sink in and being grateful for them.

Having mentored others quite a lot over last year, as well as before, and also invested in some coaching for myself — everyone needs a boost from time to time — the feedback was reinvigorating to receive.

So I wanted to write a thing to celebrate my adventures, combined with the curiosity and resilience that makes them possible.

While I can’t hope to condense everything into a short post, here’s a celebratory bullet point summary of some things that I’ve learnt through 10+ years of adventure and discovery:

  • Everyone has permission to try
  • Technical skills come and go, attitude is for life
  • Keep your spark and curiosity, it’s what makes you valuable. Nurture and protect it
  • Health and well-being are paramount. Invest in them for yourself and others
  • Leading is by example
  • Turning up when things are bad, as well as good, is a chunk of the battle
  • No stumble is fatal, give yourself time to regroup and then stand back up
  • Insight is formed through varied inputs + processing + pattern recognition
  • Resilience is just saying “I can” and going round again
  • Don’t confuse technical knowledge (which is learnt) with capability (which is a combination of attitude and aptitude)
  • Our perception of ourselves is not a reflection of others’ thoughts about us
  • Sometimes you must just do it, irrespective of the evidence or the perceived wisdom of what you’re going to do
  • Doubt is normal, acknowledge it, try to mitigate it and keep going
  • Investing in people is the best; generosity with time and support of others multiplies your impact
  • Culture keeps you afloat when the seas are stormy
  • It’s okay to feel unfinished; unlearning/learning and adaptability are so important
  • Don’t be afraid to try out alllllllllllllllllll the hats
  • Have confidence, beware of overconfidence and believe you’ll figure it out (or learn a lot trying to)
  • Listen, you’ll learn a lot more. The more you learn the more connections you make and patterns you’ll see
  • You define your work (not the other way around)
  • Get out of your head and into the real world
  • Being human and having empathy is a firm foundation, your whole self does not need to be hidden
  • Whatever the challenge, lightheartedness makes it sustainable
  • Timebox everything, whether it has a deadline or not
  • You’re freer to choose than you think, or are sometimes led to believe

After 10+ years of adventure I’m pleased to say that I still haven’t reached my edge. The horizon keeps on expanding, and so do I. In capability, empathy, inquisitiveness as well as resilience.

My past self would have been emboldened and inspired to end up here, even if it’s still a step on the journey. What he considered risky is no longer a risk. Risk would have been standing still. The adventure is a reward in and of itself, and I hope it will long continue. I’ll be doing everything I can to make sure that’s the case.

I’ve never felt so sure that feedback, learning, attitude and a growth mindset are key for both yourself and those around you to thrive, and to continue doing so over extended periods of time. It’s a marathon, after all.

You have permission to try. Not from me, though you have that too, just inherently. So my questions to you — whatever stage of your own journey you’re on — are:

What will you do when you’re free to choose? What you should do? What do you want to do…? What could you do? What’s stopping you?

If you liked reading this you might like this podcast I was on recently, where I talked a little more about some of this. It’s also on Apple, Spotify, or Google.

Have a listen and let me know what you think — my DMs are open on Twitter.

That’s all folks! I’m off to celebrate both the last 11.5 years of adventures and those yet to come!

🥳 Thanks for reading! 🥳



Adam Oskwarek

I help build and grow things on the internet. Product + People + Growth. Together we can go further. “chief climate officer” @ Zopeful.com