Episode 557: How to maintain friendships as a small business owner

Oct 6, 2025

Navigating friendships as a small business owner can be tricky, especially with former colleagues. Discover how less frequent but deeper connections can enrich your relationships. Explore creative meetup alternatives, like walking meetings and friendship retreats, to fit your busy schedule. Learn how to leverage technology for maintaining long-distance bonds while keeping that personal touch. Plus, find out how honesty about your limitations can actually strengthen friendships, which in turn support your business success.

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ADVICE

Redefine Regular Contact

Redefine what 'regular' means for friendships and set a realistic rhythm that fits your life.
Treat scheduled friendship time as sacred and consistent, even if less frequent.

ANECDOTE

Quarterly Long Calls With Distant Friend

Fiona describes a friend in Amsterdam with whom she meets quarterly for long Zoom calls and stays in touch on WhatsApp.
They met once in real life for a four-day visit that provided concentrated quality time.

ADVICE

Rethink How You Catch Up

Think outside traditional evening meetups and create new catch-up formats that fit your energy and schedule.
Try walks, Saturday coffees, monthly full-day meetups or short friendship retreats instead of weeknight dinners.

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In this episode you'll learn:

How to maintain meaningful friendships when you transition from employee to business owner, especially when your friends were former colleagues
Practical strategies for redefining "regular" contact - why quarterly deep connections can be more valuable than frequent surface-level catch-ups
Creative alternatives to traditional evening meetups that work better for busy entrepreneurs, including weekend activities, walking meetings, and annual friendship retreats
How to use technology strategically for maintaining long-distance friendships without losing the personal connection
Why being honest about your capacity strengthens rather than weakens your friendships
The crucial role friendships play in business success - providing perspective, emotional support, and a safe space to process entrepreneurial challenges

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