What My 2020 Startup Experience Taught Me About Work (and Life)
By: Riche Lim
Tags: Work, Startup Lessons, Startup, Entrepreneurship, Life

Photo by Priscilla Du Preez on Unsplash

I’ve always hated riding rollercoasters. I hate the exact moment when the cart pauses at the peak of the ride — I would cover my eyes and wait for the ride to be over. I don’t mind the height or speed, but I hate not knowing what turn or slope will come next. The anticipation made me anxious.

Reflecting on the last ten months of my startup experience, I am still in disbelief at how unpredictable the journey was so far. The rapid pace and the constant firefighting came as no surprise — I knew these coming in.

But what shocked me was how my mindset changed. I am no longer anxious about the unpredictability of work or the impossibility of anticipating change. I now uncover my eyes, raise my arms, and just lean into whatever direction the ride is headed.

So, what’s changed? I did not gain clairvoyance overnight, nor did my experience allow me to anticipate the future better. I learned to think differently — to stop worrying about what’s ahead and just enjoy the ride.

Here are my five lessons from 2020 that drove this mindset shift:

I don’t know what’s ahead, but I know I’ll figure it out.

As an analytical person, I find spreadsheets and quantitative analysis comforting. But as good as spreadsheets are as a decision-making framework, no amount of statistical work can predict uncertainty.

Work and life don’t work in averages, the ‘seasonality’ of our good and bad moments doesn’t manifest according to a historical schedule. I cannot model unexpected surprises, so I no longer stress myself out trying to analyze them.

Rather, I simply believe that I (with the amazing people I work with) can figure out whatever problem comes along — and that is enough certainty for me. With that faith, the discount rate of my projections becomes zero.

When the cart is burning, put out the closest fires first.

In the early days of my career, a key success metric was clearing out my inbox. Productivity was the sole determinant of job progression. But as the scope of my responsibilities widened, this method was no longer feasible.

Solving big challenges requires more than productivity. It requires the clarity to prioritize key issues, and the emotional maturity to acknowledge your finite capacity.

When everything comes at you all at once, put out the biggest, closest fires first. Be willing to leave the rest of the fires for another time, or for other people. You only have one extinguisher.

Problems are opportunities when flipped upside down.

I struggled with my work-from-home setup the first few months — I was ill from extended screen time, and felt emotionally drained from the lack of human connection.

But these challenges were also opportunities for new forms of personal and professional growth. I connected with many old friends all over the world (and made new ones), participated in remote global conferences, and freed up a significant time for reading and writing.

While I deeply empathize with the mental health challenges that come with remote work and social distancing, lingering in misery has never been helpful for me. Instead, I found ways to turn these challenges into opportunities.

Lean into the changes.

My role changed many times the last six months, and I benefitted from the dynamic setup. Each new responsibility broadened my viewpoint of the business, and taught me what my strengths and weaknesses were.

The changes made me nervous, of course. This constant shift contradicts my instinct to seek stability. Having new roles mean I’m starting from scratch — I need to develop a new set of skills and adapt to a new routine.

But rather than feeling rattled, I was excited. The influence of these changes on my sense of self has largely to do with mindset. Instead of seeing these changes as disruptive, I leaned into these changes and saw them for what they were— a new realm of possibilities.

Enjoy the ride and don’t throw up.

Here’s my most crucial lesson: No matter how ambitious, noble, or world-changing your work is, no matter how many people’s livelihoods are at stake, the most important person in your journey is you.

The time you allocate for your happiness and well-being does not compete with the time you spend fulfilling your purpose and mission. Rather, your happiness and well-being are pre-requisites to doing meaningful work.

Your work (and life) is a rollercoaster, but it is your rollercoaster. If you are anxious and cover your eyes the entire time, then what’s the point of riding? Set the pace, height, and complexity that works for you. Find the setup that brings you joy and pushes you just beyond the edge of your comfort zone.

And if you get dizzy, pause the ride. Get out and take a breather. Don’t make yourself miserable; don’t throw up.

The ride of work and life is a thrill, but only if you go through it with your arms stretched out and your eyes wide open.

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