099: Austin Kleon on the Challenges of a Creative Career [Podcast]

When you set out to do creative work for a living, there are unexpected obstacles you face, things like finance and marketing, which can add up to a lot of work that doesn’t necessarily feel creative. So what do you do?

How to Write an Overnight Best-seller in Under a Decade: Interview with Austin Kleon [Podcast]

The question is worth asking: Is getting paid to do what you love really worth the cost?

Often, career experts talk about the grind involved in turning your hobby into a career. But few acknowledge the price you pay after you achieve your goal.

The part we tend to overlook is when you trade your day job for a dream job, it’s still a job.

As a self-proclaimed “writer who draws,” my guest on the podcast knows this better than most. This week on The Portfolio Life, best-selling author Austin Kleon and I talk about the tension between a creative career and the business it takes to support it. Austin has a unique but practical perspective on doing creative work without losing that edge that got you the job in the first place.

Listen in as we discuss juggling the administrative work alongside the creative work and decide for yourself if the leap is one worth taking.

Listen to the podcast

To listen to the show, click the player below (If you are reading this via email or RSS, please click here).

Lessons on art and self-promotion

Here are a few quotes from out interview that stuck with me and the lessons I took away from each of them:

1. Writing can be a way to work through your own struggles while helping work through theirs.

“Show Your Work was me actively trying to communicate about self-promotion to people who hate self-promotion, because I hate self-promotion.”

2. Focus first on creating something worth sharing before you worry about how to promote or publish it.

“Most questions about publishing and getting your creative work out into the wild is about self-promotion and marketing… The questions presuppose you have something worth sharing in the first place.”

3. Self-promotion doesn’t have to be selfish. Being generous with what you share is the best way to get your work to spread.

“If I share enough, if I’m interesting enough, and helpful enough to enough people, eventually good things will happen to me.”

Show highlights

In this episode, Austin and I discuss:

  • How reading fuels inspiration
  • Understanding seasons of creative work
  • Being comfortable with fluctuating productivity
  • One question I (Jeff) am embarrassed to answer
  • The importance of allowing margin for “ramp up”
  • What is more valuable than the amount of time you have
  • A common myth we believe about successful authors
  • How to run a business while still getting your creative work done
  • The timeline of Austin’s journey to best-selling author
  • What to do when you feel like a fake
  • Why you may not want to make a living with your art

Quotes and takeaways

  • ”If I had a choice between having a full day vs an hour every day to work, I would pick the hour every day every time.” —Austin Kleon
  • Sometimes you don’t know who you are writing for until someone starts listening.
  • “Look at the world and write the book you think is missing.” —Austin Kleon
  • Some of history’s greatest artists did their best work later in life
  • “Instead of making a living doing what you love, what can you do for a living that means you get to spend the most quality time doing what you like?” —Austin Kleon


How do you balance administrative and creative work? Why are (or aren’t) you pursuing a creative career? Share in the comments

9 thoughts on “099: Austin Kleon on the Challenges of a Creative Career [Podcast]

  1. I beg to differ. I see this artist post his work daily and now I am tired of seeing his work, I don’t see it any more when I see it. I think it is better if he posted a couple times a week giving people time to miss his work

    1. Everyone has a right to their opinion and I am sure you have a reason for yours. Can I ask a question? You start with “I beg to differ” What is it that you “differ with?”

  2. I juggle a professional career as a police chief with a part time career as an artist/writer. I rise early, keep a creative schedule and built habits that support my painting and writing. And I concur that generosity goes a long way towards fueling one’s passion.

    1. Wow that sounds challenging. I work a full time job myself and try to kep up with two blogs, a dog breeding business on the side. I also draw and paint when I find the time. Sounds like I would do well to have a more structured schedule.

  3. Enjoyed listening guys! I really appreciate the comfortable feeling of the podcast. I feel like I was just hanging out with some guys talking but there are some really great take aways here.

  4. Great discussion! I’m a DJ/music producer, but I do have a day job. I tried doing music full-time for a couple of years and it was just too tough. I prefer being financially secure so you don’t have to think about money with artistic decisions…

  5. Wow guys, this episode really connected.

    I feel like I’m in the middle of this right now, and I needed to hear some straight up truth about being a full time creative.

    I love writing novels, but I know I need to share what I’ve learned on top of publishing novels to make a living as a full-time creative. Of course, I’d always prefer to be writing my novel during my limited free time, but the other teaching side is what will help me become a full-time creative sooner than later.

    I’m always imagining what it would be like to escape my corporate 9-5 job, and your convo grounded me for what to expect when I reach that goal.

    Thanks again, and I just purchased Steal Like an Artist to start down Austin’s rabbit hole of stuff.

  6. Great interview. I really enjoyed it. Simple things like “Setting aside a little chunk of time every day I think is way more powerful than having these big blocks of time freed up.” were very important for me. I like to think I have no time. But that is mostly an excuse. Thanks!

    You mentioned an infographic of Lewis Hyde and you wanted to share the link. I am just curious. Could you please share it?

    Again, thank you for all your work and this great podcast -Astrid

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