Bloggers September 27, 2020

40 lessons for aspiring creators

Jay Clouse @jayclouse

A few years ago, I set out on a journey to earn an independent living as an entrepreneur. I actually wasn't sure what that would look like...but while I figured that out, I figured I'd get by through freelancing.

Over time, I learned more about digital creators and began to recognize that my aspiration to earn an independent living was merging with my aspiration to become an independent creator.

I'm really proud of what I've built so far! Every month I earn income through a portfolio of sources, including podcast sponsorship, affiliate revenue, course sales, royalties, reader support...not to mention clients!

And I feel like I've reached a point where I can take a deep breath and say, "OK, this is working!" But that point came after a lot of trial and error, and some misguided efforts.

Lately I've had conversations with aspiring creators who have been curious to learn from my journey. And I wanted to share a lot of the lessons I've shared with them here via email.

I'll probably flesh this out into an actual article, but here's a list of what I wish I would've known sooner (in no particular order):

  1. You are creative. Everyone is creative.
  2. You don’t have to be a "guru" or an expert – just be a person, learning in public.
  3. Don’t reinvent the wheel, but don’t blindly follow the model either.
  4. Relationships with people that know, like, and trust you is more valuable long-term than anything else.
  5. One of the best ways to strengthen your relationships is to be the bridge connecting others.
  6. Being a creator helps you to form those relationships at scale.
  7. Consistency is an important part of building trust with your audience.
  8. Consistency comes at a high cost – your time. Are you willing to commit that?
  9. Find ways to create value for others first. Worry about capturing part of it once you've solved for creating it.
  10. Writing doesn’t need to be profound – it needs to be relatable.
  11. When you're telling a story, don't be the hero. The viewer is the hero, and you are there to be a guide.
  12. Your trajectory is more likely to be quickly impacted by distribution rather than quality of work.
  13. Play nicely with search and discovery engines – their distribution will help you build more quickly.
  14. Ultimately, even if you have distribution, you need to be sharing your unique voice.
  15. You need reps to build confidence and find your voice. So don't beat yourself up if you prioritize reps ahead of discovery.
  16. This all takes a long time – so start ASAP!
  17. Find a platform and medium you enjoy. You’ll need enjoy the process long before you can ever enjoy the results.
  18. In the beginning, you will still be feeling things out. But you'll know when things feel directionally correct.
  19. Once you decide what you want to create and share with the world, raise your quality standards.
  20. As you really narrow in on your direction, try to be world-class.
  21. Audio, video, and editing skills will save you a lot of money and cost you a lot of time.
  22. No matter the medium, you'll still need to get comfortable with writing.
  23. Start with ConvertKit.
  24. Don’t even look at who unsubscribed.
  25. Your early subscribers will be friends, family, and haters (almost all of whom aren't your target audience).
  26. You'll see a dip in attention a few weeks or months after starting. That's OK – it's just a cleansing.
  27. Don’t let money impact your expression. Find ways of earning an income so you don't poison your work.
  28. When you’re afraid to hit publish, that’s probably your best content. Listen to that signal and follow through.
  29. Rejection gets a lot easier over time. Once you're comfortable with it, that's a super power.
  30. Your "launches" will be underwhelming. Be thankful for the small wins.
  31. People will be less supportive than you’d think. But no one owes you anything – be grateful for every ounce of support.
  32. You can stand out by being personally supportive of other creatives. Be a power up.
  33. Don’t react emotionally. Pause, reflect, and respond appropriately.
  34. If you don’t want to do __, don’t tell yourself that you have to. If you hate doing it, we will sense it.
  35. Do one platform/medium well. Focus is a skill.
  36. You need to be willing to share your ideas and your work. Otherwise, you can’t help anyone.
  37. A “niche” can be created at the intersection of your unique interests or talents.
  38. Plan your time around when you have your best creative energy.
  39. Being polarizing leads to faster growth. That doesn’t mean it’s worth it.
  40. Your opinions will change. That’s OK – just be honest about it.


If any of these resonate with you, I'd love to hear it! Reply and let me know.

This was originally shared via my newsletter.

  1. 2

    Thanks for the great insight. Several lessons resonate with me, for example #30 and #31. I learned #31 the hard way.

    In #15 what do you mean by reps?

    1. 1

      Thanks so much! By "reps" I mean repetitions. Experience, essentially.

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