Creativity and Entrepreneurship (Part 2)



Quitting my job to blog for a living was so embarrassing.

It didn’t seem like a “real job”.

People would always ask me questions like: “So what exactly is it that you do?” And I never knew how to answer them.

(Actually, I still don’t know how to answer that question.)

It’s been five years now, and I’m so glad I took that dorky risk.

As I reflect on these past five years and share what I’ve learned, my default is to focus on the creativity aspect. I love talking about how to show up every day or how to build an audience of awesome and smart people. I want to dive in to to the topic of doing our best creative work.

But over these past five years I’ve also learned about bootstrapping and running a business. I’ve learn the ins and outs of starting and building a business through experience, trial, success, and error.

There is so much involved with being an independent creative entrepreneur.

For one, you have to have the creativity side. This includes:

  • Finding own vision and voice for your creative work;
  • Showing up every day to do that work;
  • Being focused with your time and energy;
  • Staying inspired;
  • Having fun.

Creativity is critical. And, as we’ll get to another time, it’s so important to show up every day to do the hard, creative work.

But just as important as creativity is the entrepreneurial side…

  • You’ve can’t be so romantic about making money that you never get around to earning a dollar.
  • You have to be willing to take risks and experiment with new ideas.
  • You have to get good at making money.
  • You have to learn how to budget, project, save, invest, make a return, and live well beneath your means. Otherwise your business will never get the financial root system it needs in order to thrive.

Creativity and business chops. You need both.

Later this week I’ll be sure to share some of the things I’ve done over the past five years to make money. But first…

Knowing that both the creative aspect and the business aspect are so important, I want to dive into what’s I think is needed to write on the internet for a living.

(This could go for just about anything, really. Writing is what I know best, but this stuff goes for podcasts, newsletters, photography, etc.)

Basically, if I were brand new and starting out fresh… if I were giving advice to my past self… these would be the highlights of that conversation.

  • Show up every day: I’m going to touch on this more, but showing up every day is vital. This is how you strengthen your own creative muscle, it’s how you improve your skills, and it’s also how you build your audience. (Recommended reading: Show Your Work.)

  • Plan ahead: It took me years to figure this one out. You’ll do better work in less time with less stress if you know where you’re going. (Not sure how to have a plan for your creative work, The Focus Course will get you there.)

  • Invest in mentorship, learning, and courses: Because you don’t have all the answers, you have blind spots, and you need someone to cheerlead for you and help you figure things out.

  • Celebrate your progress: When you’re able to recognize that you’re making progress in your work, it helps you stay motivated. Also, journaling about your business and creative endeavors as you go through them today is an asset you can use in down the road as a sort of “advice to your future self”.

  • Sell stuff: You get good at making money the same way you get good at anything else: practice. So, sell early and sell often. This will help you learn about pricing, sales, and providing value to others. It also helps you to get comfortable with charging money for the work you do. Something many of us aren’t naturally comfortable with.

  • Automate / eliminate / delegate as much as possible: It seems everyone know says they waited too long before learning to delegate. This is a great way to break your broken workflow habits and free yourself up to spend your time better. And it’s not just for the sake of being more “productive” at work — it’s also so you can have more down time to rest, think, and be with friends and family.

  • The tools you have are almost certainly good enough: This one applies to the nerds in the room. I’m an incessant tinkerer. While it’s fun to always be looking for the next best thing, it’s also a huge distraction. Maybe it’s my old age, but I’m far more content with the tools I have today that I ever have been. If it works well and helps me do what’s important, then I’m not going to try and replace it just for the sake of change.

  • Always be honest and sincere: This is critical because the best way to build an audience is through trust. Being genuine and telling your story is how you build trust.

  • Work hard, but don’t work nonstop: Easier said than done for many of us. The ideas and action items are never-ending. That’s why I schedule my time off and even plan ahead for how I’ll spend that down time. Otherwise my tendency is to work on just one more thing.

  • Have an ideal reader / customer / client / fan: When I first began writing, there were two specific people who I wrote for. I would always gauge my articles and topics through their eyes, making sure I was writing something that would be interesting and helpful to them.

    Now that I’m working on building The Focus Course website, we’ve spent a ton of time defining what our ideal customer looks like. We’re using surveys, personal emails and conversations, and more. It’s a much different approach than just guessing or making stuff up, and it means we’re actually able to help people with what’s most important to them.

  • Take risks: Every time I’ve felt out on a ledge, not sure if something would work, it turned out pretty great in the end. This is not an advocation to be reckless, but it is permission to try something new.

  • Trust your gut: I don’t know about you, but I spend a lot of time second guessing myself. I question if I’m doing things right; if I’m missing something; if I’m even making progress. Other people can give advice and input, but to do your best creative work you’ve got to follow the dream in your heart.

    Not to go all Mr. Rogers here, but it’s true. If you’ve got an idea or a hunch that just won’t let go, then focus on it.

Which is why, if I had to boil it all down to what I consider to be the most important advice I have for creative entrepreneurship, it would be this: focus on consistency and honesty.

We’ll dive more into that one tomorrow.