Podcast Summary:

This Can't Be That Hard, Episode 345
"The Art of Building a Business That Lasts" with Leah O'Connell
Host: Annemie Tonken
Guest: Leah O'Connell
Date: December 2, 2025

Overview

In this episode, Annemie Tonken sits down with Leah O’Connell (host of "Photo Fuel"), for a thoughtful, wide-ranging conversation on what it truly takes to build a creative business that stands the test of time. They explore entrepreneurship’s real risks and rewards, overcoming ego and failure, staying creatively engaged, adapting to change, and the practicalities behind building stability—especially through innovative models like memberships. The tone is candid, encouraging, and filled with actionable advice for photographers and creative entrepreneurs.

Key Discussion Points & Insights

1. Entrepreneurship: Risk, Pressure, and Perspective

• The Myth of Arriving: Annemie reflects on the shift from feeling like a "super newbie" to a trusted expert, emphasizing that self-doubt never fully disappears for entrepreneurs. (02:50)
• Risk Is Relative: Drawing from her background in healthcare, Annemie shares that the risks in photography feel much smaller compared to life-and-death decisions in nursing.
  • Quote: "If I flub a session... or make an investment that doesn't pay off... what's the worst that could happen? I could be embarrassed... maybe I would lose some money, but I wasn't out there risking my grocery bill." – Annemie Tonken (04:24)
• Failure Is Part of the Process: Growth often comes from stressful turning points, and avoiding risks usually means missing crucial opportunities. (08:35)

2. Ego, Failure, and Misalignment

• Fear of Embarrassment: Ego isn’t inherently bad, but fear of being wrong often prevents necessary risk-taking.
• Quitting vs. Misalignment: Leah differentiates between quitting and recognizing when something doesn’t fit, suggesting entrepreneurs reflect and "iterate" rather than simply give up. (11:29)
  • Quote: "It's different than just being like, well, I tried it and didn't work, and now I'm done." – Leah O’Connell (11:29)

3. Parallels to Parenting and Life Advice

• Advice to Our Kids, Advice to Ourselves: Annemie shares a parenting story about resilience and not giving up—which she finds applies equally to entrepreneurship.
  • Quote: "Sometimes as a parent... you find yourself telling your kids something, and then... you're like, I need to listen to that advice 100%." – Annemie Tonken (13:05)

4. Ideal Clients and Flexibility

• Evolving Avatars: Ideal client profiles are useful but rarely perfectly realized. Business owners and their clients both evolve, requiring regular reflection.
  • Quote: "I am still kind of refining my ideal client avatar... and you wouldn't know that if you were inflexible." – Annemie Tonken (15:38)
• Artistic Growth and Avoiding Burnout: Creative entrepreneurs often crave novelty after mastering a skill. Flexibility prevents stagnation and burnout. (16:40)

5. Traits of Businesses That Last

• Main Thread is Grit: The people who stick with business are those willing to try, fail, and try again—adapting their strategies each time.
  • Quote: "If you are in business long enough, you will fail, period... but also the willingness to try again with the information that you've gathered from those." – Annemie Tonken (18:53)
• Flexibility Required: Long-term success in creative business means flexibility in both art and business systems. Platforms, client needs, and markets all change. (19:53)
  • Quote: "A willingness to be flexible, learn new things, try new things... it's one of the necessary muscles to build if you want longevity." – Annemie Tonken (19:53)

6. Balancing Consistency and Change in Your Creative Brand

• When & How to Pivot: Dramatic changes (e.g., editing style, pricing) can work but require patience and clear communication. Some clients will leave, making room for better-fit clients.
  • Quote: "When you make a major change... be aware that big changes leave a space of time where you have to then find your new people." – Annemie Tonken (23:06)
• Risk and Reward: Reiterates that business changes are not life-ending; worst-case scenarios are often manageable with backup plans. (24:27)

7. Financial Reality & “Supplemental Income”

• Money Gaps and Survival: Annemie and Leah emphasize that building a stable business takes time. Sometimes, filling income gaps with outside work is not only okay but can be necessary and strategic.
  • Quote: "There's no harm or shame in that. In fact, it's just another tool in your toolkit that builds your resilience." – Annemie Tonken (26:20)

8. Defining Success for Yourself

• Making Your Own Rules: There’s no singular right way—success looks different for everyone.
  • Quote: "Every editing style, every service style... somebody’s making it work." – Annemie Tonken (28:53)
• Adaptability in Service Offerings: An example is shifting away from in-person sales when it doesn’t suit your life, underlining the need for business practices to support your needs, not the reverse. (29:11)

9. Stabilizing Income with Memberships

• Why Memberships Work: Annemie describes how creating a membership model provided stability—giving clients an easy way to book and budget for recurring sessions and giving the photographer monthly income.
  • Quote: "A portrait membership is such a great stabilizer in your business... You essentially give yourself a paycheck that you can rely on, plan around... it's like the golden ticket in this industry." – Annemie Tonken (32:16, 34:19)
• Client Loyalty: Memberships reduce churn and keep clients "off the market," building loyal repeat business.
  • Quote: "It effectively takes your clients off the market and just makes them exclusively yours." – Annemie Tonken (36:17)
• Marketing Shift: Email lists and memberships now outperform social media as effective, predictable ways to stay top-of-mind with clients. (34:19)

10. Nurturing Creativity and Avoiding Burnout

• Returning to Joy: Annemie shares that personal photography—shooting for herself and her family—is what nourishes her and helps her stay grounded, especially during bleak times.
  • Quote: "Photography is my go to for when I am feeling overwhelmed by the external world. It is a place that I can reliably go to find beauty..." – Annemie Tonken (37:48)

Notable Quotes & Memorable Moments

• “I'm worth banking on. Yeah, why not? And I often will look around and be like, if them, why not me?” – Annemie Tonken (08:08)
• “The word ‘never’ is just like, it's a dangerous word.” – Annemie Tonken (18:53)
• On Membership Stability: “If you belong to [a membership], you're already paying for that... even if that's a better price than what you're paying for your membership, you're like, yeah, but I already, that box is checked. I'm not on the market.” – Annemie Tonken (36:17)
• On Balancing Business and Art: “Approach business with as much creativity as you do your art because there's so much out there.” – Annemie Tonken (20:33)
• “It's not all or nothing. You can say, I'm going to try something different... your business can live to see another day.” – Annemie Tonken (26:20)

Timestamps for Key Segments

• 02:50 – Annemie discusses imposter syndrome and entrepreneurial growth
• 04:24-08:35 – Risk, pressure, and finding perspective from a healthcare background
• 11:29-13:41 – Quitting vs. misalignment, learning from failure
• 15:38-16:40 – Ideal client evolution and creative burnout
• 18:05-19:53 – Traits that foster business longevity: resilience, flexibility, and learning from mistakes
• 21:45-24:27 – Balancing consistency and change in art, messaging through pivots
• 25:42-27:48 – Being candid about money, filling income gaps, and inevitable ups and downs
• 30:01-34:19 – Implementing systems, intro to the membership model for stable revenue
• 34:19-36:17 – Email lists and memberships as new stabilizing/loyalty tools
• 37:48-39:14 – How personal photography can refuel one’s business and passion

Conclusion

This episode is an honest, insightful guide to building a lasting creative business on one’s own terms—blending heart, strategy, acceptance of risk and failure, and a commitment to ongoing creativity. Among the most powerful takeaways: flexibility, resilience, and designing your business and success around your true needs and values, not external expectations.

Resources:

• This Can't Be That Hard
• Revenue on Repeat (membership course)

This summary covers the essential discussions, advice, and memorable quotes from Annemie Tonken and Leah O’Connell, in the spirit and tone of their original, encouraging conversation.