In this episode, Tim talks with cartoonist, writer, and teacher Emily Flake about building a creative career through multiple income streams, persistence, and adaptability. Emily shares what it’s really like to work in fields where rejection is common, success is unpredictable, and financial stability requires constant adjustment. Together, they explore the tension between creative fulfillment and practical money decisions, including saving, budgeting, and long-term planning. One Key Takeaway: A sustainable creative career is built less on sudden success and more on resilience, flexibility, and steady habits that support both artistic and financial health.

Emily’s question for Tim: I’m a freelancer whose income varies wildly, and not only am i terrible with money but I’m actively afraid of thinking about it. I play chicken with my bank account, which is a checking account, because i don’t have a savings account. Don’t you dare even ask if I have a retirement account. I’m 48 gd years old. I guess my question is: how fucked am I?

Key Takeaways:

1. Emily Flake describes how her career has been built from many different income streams, including cartooning, writing, teaching, comedy, and running creative programs, rather than from one single job.
2. She explains that publishing work in prestigious outlets like The New Yorker brings visibility and credibility, but does not guarantee long-term financial security.
3. Emily talks about the ongoing reality of pitching work, receiving rejections, and learning to persist in an industry where “no” is far more common than “yes.”
4. She reflects on how she balances creative fulfillment with practical concerns like paying bills and maintaining steady income.
5. Emily speaks candidly about her discomfort with money, budgeting, and long-term financial planning, and how this has affected her decisions.

Links:
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Emily's website
St Nell's Humor Writing Residency
Emily's contributor page at The New Yorker