“How do you work past self doubt?”

u/blinkycake writes:

I have a talent for art and a desire to start a creative career of my own making, but feel like I’m being held back by doubts about creative careers. I’m about to be 35 and want to start a creative career in art (freelance illustration and painting) and I’m haunted by the words of my mother when I was a teen that I wasn’t competitive enough and that I’ll starve. It’s an awful thing to hear as a teen when every year before college mattered you were told you were artistically talented by everyone…I haven’t been able to let it go nor the desire to create.

I know I want to do this because I’ve not been able to let go of the wonderful feeling it is to paint, I’ve tried, but the doubt I have that it’s a viable career move keeps my paralyzed–even though I know plenty of creatives who make it work and struggle through it. That worry is even greater than my hate of being managed/working for a company… I’ve heard all the advice that I should just keep it a hobby, but given that every decent paying job I’ve had sucks up the space in my head, that doesn’t work.

If you have a creative career or business, how did you push past the doubt? What keeps you making your next creation no matter the outcome?

Here’s my comment:

I wrote and published a book on creativity, full of prompts for people getting into it—like you! Some potentially useful prompts:

  • Set a 10-Day Quota: Pick an activity and commit to doing it for 10 days in a row. (You can also try a daily challenge like SketchDaily, Inktober, 250 box challenge, etc.) This will help you build your confidence in your consistency and practice.
  • Complete Your Operation in Seconds: Simplify your creative operation, moving the starting point to the finish point much closer together—mere seconds apart. E.g., create an interpretative drawing from the first thing you see when you open up a website, etc.
  • Set up Surfaces: Set up at least three different surfaces—one for storing your works in progress, one for sending to other people for feedback, and one for displaying your finished work.

I’m a non-fiction author with a day job. Re: doubt, I built confidence by saving money, taking sabbaticals and practicing writing full-time (wrote the drafts of my book). 

I developed the confidence by tasting what full-time authoring would feel like, and dealing with the harsh realities of it. (Not as much time to write as I would have thought! Amidst the book promotion, pitching, etc.)

What keeps me making: 

  • The process of writing is super fun and rewarding for me (I blog every day and will paste a version of this comment there)
  • The momentum from the book supports me emotionally (I do one promotion-related task every day, takes ~5–15 mins)
  • I am free to pursue my whims and interests because I don’t rely on writing for living income (which wasn’t the case when I did it full-time)

You mention a day job tends to take up too much space; is it possible to augment your art income with freelance art/design/commissions? Or through a less taxing part-time job? I saw someone else mention occupations such as paint night, etc. Philip Glass drove taxis because it didn’t take too much mental space/commitment; is there a job you can take on that sounds more like this?

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