24 in 24 | Life lessons learned in 2 years of working at a startup

anour olh / pexels

After years of working as a creative in the ad agency world, I learned a lot. How much retouching it takes to get that iced coffee to look justtt iced enough, and the hex code for the most perfect caramel color. How the heck you get a CGI buffalo to sit on a couch and talk, while making it look believable in a tv commercial. That two drinks will get you through an engaging dinner conversation with the client…four, well you better start heading to your hotel room.

But somewhere between pouring my heart into work that never saw the light of day, 70+ hour weeks, and ego driven account directors, I decided to leave. The swanky offices with stunning views and free flowing kegs couldn’t keep me from feeling my time had expired.

At one point, I was so desperate for an out, I applied to a job as a white water rafting guide. I took the call, nearly moved to Montana on a whim with no experience, and ultimately chickened out. I then proceeded to accept a random design gig in Utah, only to back out last minute knowing in my gut it just wasn’t the right fit.

Well, that’s when I found a startup in the area looking for a designer. Maybe it found me. I never heard of it before, and I certainly wasn’t looking into startups…what does series c funding actually even mean? Regardless, I was intrigued by the brand and the product. The core values were seemingly more aligned with my lifestyle and passions, far beyond any other brand I had previously worked on.

One call, one in person interview, and a job offer later that afternoon. I was honestly a little terrified to say the least. Excited, but terrified. They don’t have a creative department, or any other creatives for that matter. No IT department? Who will fix my computer? What if the company is a total flop in 6 months? Eh, I probably won’t stay more than a year anyways… signs offer immediately.

Now, it’s been been exactly *blinks* two years since I started, which makes it a great moment in time to pause and reflect over these past 24 months. I honestly never expected to be in this position, but couldn’t be more grateful for the journey that I landed in. My experience to this point has been the greatest lesson not only for my career, but life at large.

Here are 24 key lessons I’ve learned over the past 24 months:

  1. Growth is uncomfortable.
    Change can be incredibly painful. Whether your marketing team just doubled its size in two months or you’re uprooting your life and moving across the country…growth never feels great in the moment, but is necessary to evolve.
  2. Embrace the uncertainty.
    Rather than letting it provoke your anxiety, let it be a source of excitement. Sometimes not knowing what’s coming next allows more room for opportunity. I can certainly say we didn’t see a global pandemic coming, and while it could have derailed our business, we were fortunate enough to pivot and let it fuel growth.
  3. Passion outweighs intellect.
    You don’t need to have the highest IQ in the room, but you better have a work ethic, drive and passion thats tough to beat.
  4. Sleeping less doesn’t mean getting more done.
    Between college and ad agency life, all nighters were a badge of honor. While startup culture may have an “all gas, no brakes” mentality, in order to be most productive during the day, you actually need to sleep (more than 4 hours a night).
  5. Speak up, even if you don’t feel like its your place.
    I’m not a copywriter or startup guru, what business do I even have writing this?
  6. If you don’t ask for what you want, you’ll never get it.
    The budget, the job title, the raise. The relationship status. The item not on the menu.
  7. Good ideas & inspiration can come from anywhere.
    From the intern who’s only worked a month, to the barista you struck up a conversation with while waiting for your lavender latte. Stay open minded with a listening ear can; you may be surprised.
  8. Experimentation is essential.
    Just because you’ve “never done it that way” doesn’t mean it’s not worth trying. Get weird, break things. FSU. We learn more from our failures than successes. Sometimes the best results are the outcome of a “happy accident” as Bob Ross would say.
  9. You won’t always have all the answers.
    Go as far as you can and fill in some of the blanks later. Waiting for all of the answers just slows down progress.
  10. Perfection can be paralyzing.
    Working at the speed of light comes with a high degree of risk and error. But ultimately, you get WAY more done.
  11. Use your resources, be scrappy.
    You may not have all the ingredients you need, but you still need to put dinner on the table tonight. And that photoshoot with a 1k budget and 1-week timeline still needs to happen too.
  12. Everyone is learning.
    And the best way to learn anything at all is to teach yourself. Printer is broken? Well we don’t have an IT department, so figure it out. Headlight is out on the car? Google it, can’t be that hard to change.
  13. You can’t do this alone.
    You may have started as a one person team, but there comes a time when you need to trust others to get the job done, and ultimately you’ll go further.
  14. Vulnerability makes you human.
    You can’t hide having a full blown panic attack during a company wide presentation—but you can admit to it, learn from it, and find courage to go forward. Taking off your armor exposes you to more authenticity, honesty, and deeper relationships.
  15. Boundaries are vital.
    Recharging doesn’t mean plugging in, it means disconnecting. I see your Slack at 8pm, but I’m also at dinner with a friend I haven’t seen in 6 months. It can wait. Toxic family member? Again, boundaries are vital.
  16. Balance is crucial.
    Work is what you do, not who you are. It can be so easy to let a demanding job steam roll straight through your social life and hobbies, and vice versa. Make sure there is something else that gets you out of bed in the morning (laptop in the kitchen doesn’t count). Balance keeps us focused, energized and less likely to burn out.
  17. Have a clear vision.
    It may be blurred sometimes, but have a good idea of what you want, and where you want to go. Where are you in 1 year from now? 5 years? A 20 person internal creative department? A house outside the city with a dog and two kids?
  18. Be decisive.
    Know what you want, because if you don’t — someone else will make the decision for you, and it ultimately won’t be what you wanted. Being direct helps reduce time wasted.
  19. Instill confidence in yourself and others.
    Even if you don’t always have it. Fake it til you make it. The car may have some dents, but you still need to sell it.
  20. Surround yourself with people better than you.
    Wether that’s the 65-year old woman training for her 4th Ironman that zipped past you during swim practice, or the 5 Ivy league grads on your team. Inspiration is far more useful than intimidation.
  21. Flexibility and adaptability.
    You can’t let a calendar change derail your week. Increasing your degree of flexibility significantly helps decrease stress. You can’t control everything, especially in a remote world. But you can mange your mindset, approach and response.
  22. Positivity is infectious.
    That idea may seem absolutely ludicrous to you. No effing way. But hey, enough conviction, belief and positivity can spread faster than COVID, and that crazy idea can become your reality.
  23. Gratitude goes a long way.
    Your wins are never yours alone. Gratitude of any size, keeps us grounded, happier, and ultimately more resilient. I am so incredibly thankful for the people I have met and and experiences work has allowed me, and I make sure to remind myself of that every day.

24. We’re all just making it up as we go.



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Ursula Nickerson

Ursula Nickerson


Actually not a sea witch. Creative director, designer, swimmer & triathlete. Mainly here for coffee and tacos.