Five Lessons About Entrepreneurship That I Learned in 2020



2020 was a hell of a year on many accounts. Entrepreneurship was no different.

One thing that can be said without question about 2020. If nothing else, the year brought forth some really funny quotes that attempted to summarize how we were feeling as the year continued to unfold and life seemed to keep unraveling.

Here are just a few from a great blog post in

“My life feels like a test I didn’t study for.” —Unknown

“So far, 2020 is like looking both ways before you cross the street then getting hit by an airplane.” —Unknown

“If you had asked me what the hardest part of battling a global pandemic would be, I would have never guessed ‘teaching elementary school math.’” —Simon Holland

Never before have humans tried so hard to use humor (and memes) to deal with the continued string of bad news, unexpected events and rapid changes to every aspect of life. Suddenly going online to look for some bright spot became like a hot cup of coffee to start the day – not essential but pretty damn close.

But as the year draws to a close I have been pondering a different thought that seems contrary to the endless waves of bad news that (unfortunately) keep coming at us.

Will 2020 go down as the greatest year ever for entrepreneurship? Or at least an entrepreneurial mindset?

Yes, this year has brought innumerable challenges for businesses of all sizes; many companies faced obstacles they never expected to. I don’t want to make light of the suffering that so many people have been forced to endure during 2020. For entrepreneurs in industries like travel, live entertainment, dining or fitness – just to name a few – 2020 has been like a horror movie that has no ending.

But has there ever been an event or time that forced business owners big and small to think differently and to do so almost overnight? To embrace change and reimagine alternatives? To develop mental toughness?

Most of the press coverage in 2020 has been about all that is going wrong in the world. But I would argue that this year (which has seemed like a decade) taught me more about entrepreneurship than any other year in recent history. In that regard, perhaps 2020 was a gift. Here are my top learnings from 2020, summarized using some of my favorite quotes (all of which were written or spoken well before 2020):

1. “Security is mostly a superstition. Life is either a daring adventure or nothing.” – Helen Keller

Companies must innovate or die. This often overused (and in light of 2020, highly insensitive) phrase came true in 2020 faster than anyone ever expected. Every business was forced to think differently about their product or solution offering almost overnight. Those who did survived and flourished. Those who waited for “all of this to end” didn’t make it. The harsh reality of this statement was never more apparent than in 2020.

2. “What good is an idea if it remains an idea? Try. Experiment. Iterate. Fail. Try again. Change the world.” – Simon Sinek

Entrepreneurs are best positioned to solve really big problems. 2020 brought so many unexpected challenges that it strained most parts of society. But solutions were quickly brought forward by aggressive and opportunistic entrepreneurs. Rapid COVID test, video conferencing solutions, restaurant delivery, educational pods, home office furniture…hell, even sweat pants had a moment. Thank goodness for entrepreneurs and innovators – they really do have the power to change the world!

3. “Everyone has a plan until they get punched in the mouth”. -Mike Tyson

Although the great boxing champion was talking about preparing for a fight, the same could be said for entrepreneurship in 2020. You can build a great business plan, financial model and strategy – but what really matters is what you do when the proverbial sh%t hits the proverbial fan. Being prepared for the unexpected is so important and expectations really matter. Starting, running and growing a business is hard in the best of times. 2020 brought a flurry of punches to the mouths of every entrepreneur – a painful reminder that achieving anything of note is always really, really hard.

4. “There are decades where nothing happens; and there are weeks when decades happen”–Vladimir Ilyich Lenin.

2020 also showed us how quickly trends can get accelerated – for better or worse. Solutions like video conferencing, remote work, telemedicine and home fitness have been slowly growing for decades. Then 2020 hits and they go from “maybe” to “must have.” The best entrepreneurs took advantage of this and saw the rewards. Be prepared, stay in the game and be ready for change – it is the only constant in entrepreneurship.

5. “I’m convinced that about half of what separates successful entrepreneurs from the unsuccessful ones is pure perseverance.” (Steve Jobs).

Mindset matters. Entrepreneurship is hard, even in the best of times. Starting and growing a business in 2020 might have been the hardest year ever to stay mentally strong and healthy. 2020 reminded me just how important mental health is for entrepreneurs. Self-care is important. No one can put their foot on the gas 100% of the time, and to achieve sustained, consistent perseverance, you have to take care of yourself.

Say what you will about the past twelve months but one thing is certain – It has been one hell of a year. Hopefully 2020 will go down in history as highly memorable – if not I am not sure I can handle what comes next! From Tiger Kings to “how it started, how it is going” it is a year that I will never forget (no matter how hard I try).

But the year also reminded me of how much the world needs entrepreneurs. And how much the world needs mentally strong and healthy entrepreneurs. Now more than ever. 2020 challenged all of us and reminded us to always expect the unexpected.
For me, I am grateful for what I learned this year and will carefully look to the heavens to ask 2020 “is that all you got”?
I will then quickly run to my basement and hope the gods did not actually hear my question!!

Happy New Year!!

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Monkey Masters: Jason Dorsey

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