259. One year in: lessons from my first year as a full-time coach, with Jeremy Cline. Change Work Life X Truth, Lies and Work

Welcome back to Truth, Lies & Work. Today we’re doing something a little different for the Christmas break. We’re sharing an episode from our friend Jeremy Cline’s podcast Change Work Life, where Al joined him to reflect on Jeremy’s first year as a full-time coach. This conversation marks Jeremy’s 200th episode, and instead of interviewing someone else, he turns the spotlight on himself. It’s a rare, honest look at what actually happens when you leave a stable career after 20 years and try to build something new from scratch. No glossy “quit and make six figures” narrative — just the real, messy middle that most founders and coaches quietly go through. Al and Jeremy dig into the emotional, financial and identity shifts that come with starting your own business, what surprised Jeremy the most, and why meaningful conversations — not logos or websites — became the backbone of his first year. If you’re thinking of going out on your own, supporting someone who is, or you're simply curious about what a year of reinvention looks like behind the scenes, this is the perfect listen for the quieter days of December. 🧠 What We Cover: The Reality of Year One Life after a 20-year careerJeremy left a long legal career to become a coach, and the biggest challenge wasn’t logistical — it was the identity shock of asking “who am I now?”. Self-employment and the fear of the first stepInstead of hiding behind planning, Jeremy forced himself into real conversations — the uncomfortable kind that actually move a business forward. The messy middle of reinventionTesting ideas, discarding bad ones, refining offers, working through insecurities — the emotional work was bigger than the strategic work. Why conversations matter more than everDespite global connectivity, genuine, real-time conversations are becoming rare. Jeremy argues that this is where opportunity lives. Opportunities come from putting yourself out thereJeremy explains how reaching out to people — including Al — created unexpected relationships, support and new directions for his business. The truth about coaching as a businessHe talks candidly about client work, self-doubt, capacity and the grind of turning passion into something that pays the bills. 🔗 Connect with Jeremy 🌐 Episode page & resources: https://changeworklife.com/one-year-in-lessons-from-my-first-year-as-a-full-time-coach/ 📬 Connect with Al & Leanne 💼 LinkedIn: https://www.linkedin.com/in/jeremyjcline/ LinkedIn (Show): https://www.linkedin.com/company/truthlieswork Al Elliott: https://www.linkedin.com/in/thisisalelliott Leanne Elliott: https://www.linkedin.com/in/meetleanne Email: [email protected] Book a call: https://savvycal.com/meetleanne/chat Podcast Website: https://truthliesandwork.com/ 💚 Mental Health Support Samaritans (UK & Ireland) – 116 123Mind (England & Wales) – 0300 102 1234988 Suicide & Crisis Lifeline (US) – Call or text 988Find A Helpline (Global) – https://findahelpline.com/