Why Most Photographers Fail (And What No One Tells You About Success)
Update: 2025-07-09
Description
Cole Roberts (Way Up North founder) opens up about burnout, ego, and building a life that fuels your creativity, not drains it.
We talk about:
- Why most photographers burn out
- What makes (or breaks) a great speaker
- Building a digital detox retreat in Sweden
- The real reason he stepped back from destination weddings
If you’ve ever felt stuck, this one will shift your perspective.
Full show notes + blog: lillyredacademy.com/podcast
Timestamps
00:00 – The truth about being vulnerable
01:45 – Why photographers burn out
05:32 – What Cole looks for in speakers (it’s not followers)
11:20 – From photographer to entrepreneur
15:04 – His 25-year vision for a digital detox resort
21:33 – The real reason he left destination weddings
29:40 – Advice for photographers who want to speak on stage
35:01 – Why Instagram isn’t the path anymore
39:50 – Building legacy through family, not just business
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