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Hi Reader, Here's a phrase I’ve been thinking about a lot lately: Don’t let planning get in the way of progress. It reminds me of when I was in high school. Anytime I had a big assignment or an exam to study for, I would suddenly decide my desk absolutely had to be cleaned first. Or my entire room. Not because it really mattered, but because it felt productive. I could tell myself I was “getting ready” to do the work, without actually doing the work. Starting a side hustle often triggers the exact same behaviour. You finally decide what you want to do. You’re motivated. You’re excited. And then your brain immediately starts listing everything you “need” first. A website. None of those things is wrong. But they’re often just modern versions of cleaning your desk before you start studying. They keep you busy. They keep you comfortable. And they keep you from doing the one thing that actually moves the needle: putting your idea in front of real people. Planning feels productive. Progress feels uncomfortable. That’s the difference. When you choose progress, you risk being ignored or unqualified. Maybe you'll discover that you picked the wrong side hustle. Here's a simple filter you can use to avoid falling into the "planning trap": If my next step doesn’t involve another human being, I’m probably still avoiding progress. You don’t need to feel ready. You need to take a step that forces feedback. Here are some examples of what that might look like:
I'll leave you with this simple question: What’s your version of cleaning the desk? And what’s the actual homework you’ve been avoiding? Do that part instead. Even if it’s messy or imperfect. That’s how side hustles actually start. Have a great week! Colin 💡ResourcesFREE! 2-Minute Side Hustle Quiz FREE! 7-Day 9-5 Escape Roadmap Video Course 30-Day Launch Playbook — Freelancer Edition |
I built a six-figure remote business and walked away from the 9 to 5 at age 46. Every Tuesday, I email a story, tip, or idea to help you climb down the corporate ladder and live life on your terms.
Hi Reader, Sharing a quick insight with you this week, as I have to catch an early-morning flight. Laura and I will be travelling for about 10 days, which means I’ll be working mostly from coffee shops, my favourite place to work! Just my laptop, great coffee, and plenty of background noise... music to my ears. _______________________ Earlier today, I was watching an interview with Seth Godin. One question he asked stuck with me enough that I paused the video and just sat there for a minute....
Hi Reader, Almost every time I go to the mall, I notice a young woman working at one of those perfume kiosks in the middle of the walkway. She’s probably 22 or 23. Part of her job is to call out to people walking by and ask them if they want a perfume sample. And almost everyone says no. Politely, but still no. But here's the thing. She keeps doing it. She simply smiles, nods, and invites the next person. No drama. No skipping a beat. I can almost guarantee you that this woman will be...
Hi Reader, I talk with a lot of people who dream about leaving the 9-5. They want more freedom, more control, and more meaning in their work. But leaving a stable, well-paying job for the uncertainty of self-employment is scary. It took me four years of preparation to say goodbye to my employer for the last time. Needless to say, it wasn't a decision I took lightly. As the sole breadwinner for a family of 5, my decision depended largely on one thing: Risk reduction. If I only had myself to...