Industry Specific Insights

Managing stress while being part of a startup

Ryan Chan

The other day, I got asked the question, “How do you deal with the stresses of building a startup”? I hadn’t previously given this question too much thought because I never identified those feelings as stress. However, it forced to take a step back and think about what do to deal with challenging situations.

(Read part 1 of growing a startup)

I realize that there have been four main points about my outlook and mindset that have not only helped me “deal” with stress and challenging situations, but also crave it. 

Love the challenge and yearn for it

(Growing up being the smallest in my friend group. Second from the left)

Since I was very young, I have always been the smallest one in my friend group. I’ve consistently been a head shorter than my friends, but I loved sports and competed as if I were the same size (I even picked up boxing with a friend of mine who was at least twice the size of myself).

I’ve always sought challenges. I wanted to push boundaries, challenge the status quo, and prove to myself and to other that the impossible is actually possible. While I’ve been wrong several times, I’ve also been right a few other times, and that’s OK! Challenging situations often comes as a result of pushing boundaries and doing what you believe is right, given the knowledge you had at the time.

Seeking that challenge has always served as a basis for what I want to overcome. It’s allowed me to uncovered a deeper understanding of the problem and push myself to always be better.

Be better than I was yesterday

The next point is having the mindset of just being better than I was yesterday. Growth compounds and I believe that my learnings have too! I’ve always had this goal for myself to just be better than I was the day before. It reminds me to cherish the small wins along the long term goal of reshaping the entire enterprise software industry.

While I’ve always had this broad goal in mind, it can also be daunting at times when I’m looking 29,000 feet up staring at the top of Mt. Everest. How can our small team of 30 people working at UpKeep, compete with other enterprise software companies with thousands of employees?

However, here at UpKeep, we move one step at a time and sometimes we sprint between steps and celebrate wins along the way. I ask myself every day, “were we better than we were yesterday“? If 30 people aim to be 1% better every single day, those other companies and our competition better watch out!

(Me falling down while learning how to ski)

It also helps remind me that when I get up after I fall down (both literally and figuratively), I know that I am just a little bit better. I’ve pushed myself a little bit more, gone out of my comfort zone just slightly more, and am on a pathway towards being better.

Having the simple goal of being better than I was yesterday is a small goal of mine that can have massive compounding effects.

Cherish the people and relationships in my life

(Recently getting married)

People in my life have enabled me and us get where we are today. I recently got married and I couldn’t be happier. Having personal relationships that mean so much to me have been one the most important factors towards my happiness and ability to deal with tough situations.

(The two men who burglarized our home)

Just three weeks ago, my house got burglarized. Two men broke into our house, stole money, jewelry, and destroyed the interior of our house, but at the end of the day, I am so grateful we were all safe and that no one was home at the time. They stole material goods, which at the end of the day are insignificant to what truly makes me happy.


(Part of the UpKeep team)

And most importantly, I am so happy with our UpKeep team and I am so grateful for all of the work that we’ve done. We have an outstanding group of people that make me enthusiastic to come into work every day. Businesses and products are built and powered by teams and this UpKeep team is one I couldn’t be happier with. Thank you to the entire UpKeep team who’ve helped us get to where we are today!

Just plain have fun

(The UpKeep team riding scooters around Los Angeles)

This last point all comes down to just plain having a good time. Take on challenges, constantly improve, cherish your relationships, but don’t ever forget to have fun.

Here at UpKeep, we may be meetings hours in a day, having tough conversations, and making decisions which could dramatic effects on the business, but we’re constantly having a good time filled with laughter and fun. I couldn’t thank my team enough for that! Their energy is contagious and is one of the reasons why I forget this notion of “stress”!

My conclusion

I’ve realized these four things help me best manage the stresses of being part of an ever changing startup! Thank you to Shelley, my family, my friends, and the UpKeep family for being part of what matters most to me!

If you’re going through a lot of stress at your workplace, I hope that this post helps out.

If you’re interested, read part 1 of growing a startup from 1-30


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