25 Things I Wish I Knew When I Was a Young Entrepreneur

Drift is the fifth company I’ve founded, and I often speak with aspiring entrepreneurs and people just starting in their career as someone with years of experience building a business.

I have one piece of advice I share almost every time: learn from someone else’s mistakes.

Simply put, learning from your failures is never fun to do. As John Lewis said, “the truth does not change, and that is why the answers worked out long ago can help you find the challenges of our time.” 

Over the past few months, I’ve thought a lot about what I wish I knew and lived by when I was younger. Here are 27 of the things learned along the way:

1. Read every day.

It doesn’t matter what. It doesn’t matter if you finish the book– just read.

2. Find mentors who have achieved success in what you want.

That could be love, happiness, community, parenting, or financially, but find someone who can help guide you. 

3. Double down on what’s working.

I also call this, “simply, focus and repeat.” And don’t stop until it stops working.

4. Avoid shiny new distractions.

There will always be a new tool, a new product, a new opportunity, a new company. Don’t lose focus on what you really want and what really matters. 

5. Prioritize learning from history.

Read books and learn from companies and trends that have lasted the test of time. 

6. Prioritize the biggest tasks each day.

These are the things that must get done. Feel no guilt if you never get to the small tasks that are inconsequential. 

7. Momentum means everything.

Keep the streak going. Search for the perfect wave and ride it as long as you can.

8. Great opportunities are much rarer than you think.

Go all-in when you find the few in your lifetime.

9. Study and restudy psychology.

Understanding social psychology, human decision making, and cognitive biases is worth more than all the leadership, business, and self-help books in the world. Seriously.

10. Be patient.

A few great actions or bets repeated is worth a million tiny actions.

11. Seek arbitrage opportunities.

Invest when others won’t, hold back when others are greedy.

12. Save for a rainy day, as it always comes. 

Avoid debt. Avoid credit. Live on less than you make.

13. Follow the “golden rule.”

You will run into people again and again throughout your life. Make sure they speak highly of you. 

14. Learn to tell stories well.

At the end of the day, most of success comes down to storytelling. This includes the stories you tell yourself as well as those you tell the world. 

15. Don’t obsessively read or watch the news.

You’ll live a more peaceful and rich life without it. We are too connected to not find out something if it’s that important. 

16. Invest in relationships.

Your community matters more than you think. 

17. Avoid conventional wisdom.

That is, unless you want average results. 

18. “Crabs in the pot” is real.

Those closest to you will try to tear you down if you try to breakout and be different. 

19. Remember that people are different but not as much as we believe. 

Again, study psychology. 

20. Take all the personality tests you can find.

Study your results. Understand how cognitive biases amplify your weaknesses. 

21. Never forget how important context is.

We always forget that every decision and reaction has a specific context, a time and place. Applying lessons learned without first considering the context will lead to unpredictable results and consequences.

22. For every reaction there is an equal and opposite reaction.

23. Travel as much as you can.

It builds awareness, empathy, and lasting experiences. Experiences are a better investment than buying things like big houses or expensive cars.

24. Pick your battles.

You don’t need to always be right.

25. When people older than you tell you that these are some of the best years of your life, listen.

Don’t roll your eyes and appreciate the current moment. You won’t regret it. 

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

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