The Creative Penn Podcast for Writers

Episode 839: Writing Free – Romance Author Jennifer Probst on a Long-Term Author Career
Host: Joanna Penn
Guest: Jennifer Probst
Date: December 1, 2025

Episode Overview

In this episode, Joanna Penn interviews bestselling romance author Jennifer Probst about building a sustainable, decades-long writing career. The discussion covers Jennifer’s persistent journey through rejection, her experiences in traditional and indie publishing, lessons learned from her viral breakout novel, business pivots, the value of diversification, utilizing Kickstarter, and the personal philosophy behind her new book Write Free. Both authors reflect on adaptability, creative freedom, and growing a body of work for the long term.

Key Discussion Points & Insights

Early Journey and Perseverance

• Jennifer’s Start in Writing:

  • Knew she wanted to write since age 7.
  • Wrote her first YA romance at age 12, inspired by a box of romance novels from her dad ([22:51]).
  • Early writing years pre-internet meant little information or community; learned from Writer’s Digest and the local library.
  • Wrote “nonstop since I was 12 years old” ([22:51]).

• Persistence Through Rejection:

  • Papered the wall with rejection slips, framed it as a rite of passage rather than failure.
  • Quote: “When I got my first rejection, I looked at it as a rite of passage... Rather than taking the perspective of, does this mean I failed? ...Perspective is a really big thing in this career.” – Jennifer ([25:16])

Breakout Success & Realities

• Breakout with The Marriage Bargain:
  • Sent it to indie publisher Entangled; it went viral in 2012 and led to a traditional publishing deal with Simon & Schuster ([25:16]).
  • Book spent 26 weeks on the New York Times list, but this did not last.
  • Quote: “I was inundated with agents and the traditional publishers came knocking… And everybody was like, wow, you're this overnight sensation. And I'm like, not really.” – Jennifer ([25:16])
  • Sudden price increase by Simon & Schuster ended the book's bestseller run ([28:08]).
  • Importance of understanding the temporary nature of success and the need for continual adaptation.

Indie vs Traditional, and the Need to Pivot

• Diversification:

  • Always sought to work across traditional, indie, and small publishers for more control and security.
  • Quote: “If one bucket goes bad, I have two other buckets.” – Jennifer ([25:16])

• Shifting Industry and Resilience:

  • Discusses industry “gold rushes,” rapid shifts in genre trends, changes in marketing channels (e.g., Facebook ads, TikTok), and the imperative to pivot.
  • Quote: “The longer you're around, I feel like you learn how to pivot if you want this career, you learn how to write differently or whatever you need to do to keep going.” – Jennifer ([30:14])
  • Both Joanna and Jennifer emphasize multiple streams of income for career stability ([27:49]).

Pen Names, Speed, and Legacy

• Pen Names & Brand-Building Choices:

  • Observes the boom in rapid release and “throwaway” pen names, especially for hitting trends.
  • Prefers organic, legacy-driven growth over short-term churn: “Every single book is like my history… I want a legacy of quality, and… a long-term backlist supporting me.” – Jennifer ([32:56])

• Balance and Real Life:

  • Life circumstances (e.g., family, illness) affect writing pace.
  • Important to have a backlist that generates income passively during slow periods ([32:56]).

Adding Nonfiction to the Mix

• Origin of Her Nonfiction Writing:

  • Nonfiction began organically when she was compelled to “pour out” advice and reflections from her writing career ([36:19]).
  • First nonfiction, Write Naked, sold to Writer’s Digest (a full-circle moment).
  • Nonfiction income and marketing are very different—lower advance, but builds relationships over time.

• Personal Impact:

  • Vulnerable truth-telling in nonfiction generated strong reader connections: “Thank you for being vulnerable.”
  • Shifted to self-publishing later nonfiction books for better rights control after Writers Digest’s bankruptcy and acquisition ([40:30]).

Crowdfunding and Creative Business Models

• Kickstarter Experiences:

  • Used Kickstarter to:
    • Relaunch an older book after rights reversion.
    • Bundle a Kindle Vella serial into a deluxe hardcover.
    • Launch a writing course for authors ([42:03]).

• Lessons Learned:

  • Don’t expect your newsletter audience to automatically support new formats or higher-priced, bundled offers ([49:47]).
  • The importance of building a Kickstarter audience, cross-promotion, and networking.
  • Budget carefully; swag can be an unexpected expense.
  • Quote: “I could not understand… why my newsletter subscribers wouldn't do the Kickstarter… My newsletter audience wants nothing to do with my Kickstarter… You need to find your streams, your Kickstarter audience, which is ads.” – Jennifer ([49:47])

• Defining Success:

  • The value lies as much in project fulfillment and creative freedom as in financial goals: “Definition of success for us… is just being able to continue doing this, right?” – Joanna ([48:35])

Embracing Creative Freedom – The Philosophy Behind Write Free

• Write Free – What It Means:

  • Book is a deeply personal collection of essays on the evolution of a writing life.
  • Quote: “‘Write Free’ is being able to write your truth in whatever day that is… Your perspective changes, your life changes and things.” – Jennifer ([56:23])
  • Encourages showing up for your writing, whatever your stage in life.

• Finding Personal Freedom:

  • Addressing mental and emotional blocks is an ongoing process involving self-awareness, meditation, therapy, and knowing yourself.
  • Quote: “You just have to go slowly and find [the answers] and then the writing more free will come.” – Jennifer ([58:07])

Notable Quotes & Memorable Moments

• “When I got my first rejection, I looked at it as a rite of passage that created me as a writer. Rather than taking the perspective of, does this mean I failed?” – Jennifer Probst ([25:16])
• “If one bucket goes bad, I have two other buckets.” – Jennifer Probst ([25:16])
• “The longer you're around, you learn how to pivot if you want this career… To me, that makes the industry exciting again.” – Jennifer Probst ([30:14])
• “Every single book is like my history... So I want a legacy of, of, of quality.” – Jennifer Probst ([32:56])
• “Write Free is an extremely personal book for me... It’s just me showing up for my writing life. And that’s what I wish for everybody.” – Jennifer Probst ([56:23])
• “Bravery. Just show up for yourself… Any kind of writing I think is therapeutic too.” – Jennifer Probst ([60:12])
• “The definition of success for us… is just being able to continue doing this, right?” – Joanna Penn ([48:35])

Timestamps for Important Segments

• Jennifer’s Writing Origin Story: [22:51]
• Breakout Success and Nuances of ‘Overnight’ Fame: [25:16]
• Traditional vs Indie – Rights, Control, and Income Streams: [25:16] – [32:05]
• Pen Names & Career Longevity Philosophy: [32:56]
• On Writing Nonfiction and Full Circle with Writer’s Digest: [36:19] – [41:30]
• Kickstarter Experiences, Lessons, and Tips: [42:03] – [53:35]
• Newsletter Audience vs. Kickstarter Realities: [53:35]
• Defining and Achieving Creative Freedom – Write Free: [56:23]
• Advice for Overcoming Mental Blocks, Writing Free: [58:07]
• Jennifer’s Online Presence and Resources: [60:30]

Where to Find Jennifer Probst

• Website: www.jenniferprobst.com – Comprehensive resource for both readers and writers; includes books, stories, videos, and resources.
• Social Media: Author Jennifer Probst on all major platforms.
• Open to Messages: Jennifer answers all emails and social media messages personally ([60:30]).

Final Reflections

This episode offers valuable perspective for authors at any stage:

• The necessity of persistence through rejection.
• The reality of career highs and lows, and the impermanence of any single success.
• Embracing both traditional and indie options as viable and complementary.
• The importance of diversification—for income, creativity, and resilience.
• Consider crowdfunding as a flexible, creative option for launching books and courses.
• Building a body of work and a legacy—defining success as the ability to keep creating on your own terms.
• Approaching writing with authenticity, personal growth, and the courage to write “free.”

For more episodes and show notes:
thecreativepenn.com/podcast