How to Think Like a Creative Entrepreneur

Note: This post is a personal running list of mindsets that we’ve refined over the years and wanted to jot down and be able to revisit/reflect on as well as add to from time to time. It’s not a prescription for how you should live, but more a reminder for how we want to live. If you come across this and find any of it useful or inspiring, that’s awesome and we hope it translates to some aspect of your life!  

How we got here

Olivia and I both started our lives on very conventional paths. After graduating from college, I was on my way to applying to med school and becoming a doctor. Olivia went on to law school and became a lawyer.

But a few years into a life that looked great on paper, we didn’t feel fulfilled. We both pivoted to working in tech for a bit before eventually working for ourselves, which has given us the most meaning and enjoyment in our lives. 

Now we’re both full-time running our various creative ventures that range from real estate, social media to e-commerce. The goal has always been to build creative enterprises that align with our interests and skillsets, is sustainable with just the two of us running it, and allows us the freedom and flexibility to live a life we love.

The process of getting to where we are now was gradual though. We didn’t go from working for corporate to working for ourselves overnight.

But each year we made conscious decisions in shaping our life to how we eventually wanted to live. And over time, we’ve built a life together that we love – one that allows us the freedom and lifestyle to pursue unique experiences and creative projects that pique our interest to the fullest.

How do we define a creative life? 

We define “creative” as something unique, imaginative, uncommon. Living a creative life to us means having to make creative decisions and generate creative ideas on a daily basis and ultimately turning those “creative” ideas into something valuable and concrete that others are delighted by in the real world. 

There’s no blueprint to living a creative life or making a living off of creative pursuits. But there are a few habits, values and belief systems that we’ve encountered and have been inspired by over the years that have helped make living a successful creative life possible. 

The best creative entrepreneurial mindsets:

1. Be maximally open-minded and curious. 

2. Expose yourself to people who have interesting, contrarian ideas who are doing interesting things.

3. Seek out novelty.

4. Travel the world. It will give you a whole new perspective and gratitude for your life.

5. Be an optimistic person.

6. Avoid depressing people.

7. Be a level 5 high agency person.

1. Level 1: “There is a problem.”

2. Level 2: “There is a problem, and I’ve found some causes.”

3. Level 3: “Here’s the problem, here are some possible causes, and here are some possible solutions.”

4. Level 4: “Here’s the problem, here’s what I think caused it, here are some possible solutions, and here’s the one I think we should pick.”

5. Level 5: “I identified a problem, figured out what caused it, researched how to fix it, and I fixed it.”

8. It’s better to be overly confident in your ability to figure things out than doubt your own competence.

9. Be biased towards action. Indecision and inaction are the death of all creative ideas.

10. There are no perfect solutions, only tradeoffs. So pick the best available solution and move forward.

11. It’s not the end of the world. Most decisions are reversible. 

12. Ideas favor quantity. Execution favors quality. Practice generating lots of ideas and then executing a few of them really well.

13. There are infinite ways to make money. Don’t limit yourself to only known possibilities. 

14. Don’t be cheap. But be smart about when and where you’re spending your money. 

15. The most interesting lives are the ones that didn’t have a linear trajectory. 

16. It’s ok to build the plane as you fly it.

17. There’s no better time to take risks than in your 20s and 30s.

18. Always have skin in the game. Wasting your own money hurts way more than wasting someone else’s.

19. Roll up your sleeves and remove the bottlenecks yourself.

20. Creativity is a muscle that strengthens with training and you can’t outsource it.

21. Cultivate good judgment and good taste. These are the people others pay to seek out.

22. Time and health > wealth.

23. A healthy mind and fit body are within your control. No excuses. 

24. Everything is downstream from mental clarity and physical fitness.

25. Speed > frugality if you believe that your earning potential is exponential. 

26. If you’re not fulfilling your dreams, you’re busy fulfilling someone else’s.

27. Consistency is easiest when you do things you’re deeply curious about and interested in.

28. Determine what type of day to day lifestyle you want first and go from there.

29. Most things don’t matter. Say no to them so you can say yes to the things that matter.

30. The 100th idea, the 100th iteration, the 100th try is the one that works.

31. It’s ok to lose interest in something.

32. Die with the tank empty rather than full.

33. You can (and should) always learn a new skill.

34. Have the courage to be disagreeable.

35. Be resolute with your goal but flexible with your approach.