194: The Three Stages of Side Hustle Self-Sabotage - Which One Is Stopping You?

If you've been wanting to start a side hustle, or grow the one you've got, but something keeps getting in the way, this episode is for you!

In my conversations with people lately, the thing holding them back has nothing to do with their idea, the market, or the timing. In every case, the obstacle is internal. They're getting in their own way.

Self-sabotage doesn't just show up once. On the side hustle journey it shows up at three very specific stages, and each time it looks a little different, which is exactly why it's so easy to miss.

In this encore episode you'll learn:

• The three stages where self-sabotage shows up on your side hustle journey and how to recognize each one
• Why "productive-looking" procrastination is one of the sneakiest forms of self-sabotage
• The escape hatch moment; what it is, when it hits, and how to push through it
• Why success itself can trigger a pullback and what to do when opportunity shows up and your instinct is to shrink
• The one commitment to make before you launch that can change everything

If you've ever wondered why you keep getting in your own way, you've landed in the right spot.

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Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things.

Have you grabbed my 28-page guide, Smart Start: From Idea to It’s Live in 7 Steps, A Beginner's Guide to Launching Your Side Hustle With Confidence? It's your complete roadmap to finally launching your side hustle.

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The Three Stages of Side Hustle Self-Sabotage: Which One Is Stopping You?

Most people who want to start a side hustle never do. And most of the ones who do start, don't finish.

If you've ever wondered why that keeps happening, to you, to people you know, the answer probably has nothing to do with the idea, the market, or the timing.

In almost every conversation I've had with people lately who feel stuck, the obstacle turns out to be internal. They're getting in their own way. And self-sabotage doesn't just show up once on the side hustle journey. It shows up at three very specific stages, each time wearing a different disguise. Which is exactly why so many people miss it.

Stage One: The Endless Prep Trap

You've got the idea. You've probably had it for a while. And on paper, it's totally doable. But instead of moving on it, you find yourself researching. And researching some more. You're looking for the perfect name, rewriting your bio for the third time, or telling yourself you just need to finish one more course before you're ready.

It feels like you're being responsible and thorough. But underneath all that busy work, there's fear. Fear of failing. Fear of looking foolish. Fear that you might actually succeed and everything will change. And then there's the other voice, the one that says, "Who do you think you are to be doing this?" That's imposter syndrome. And it visits everyone.

Here's what I know after 40 years in the personal development space: Confidence doesn't come from merely thinking about it. Confidence comes from taking action, and getting a result. That provides feedback, you learn, then you adjust accordingly. So the next time that voice tells you you're not ready, ask yourself, what would I do right now if I were ready? And then go do that thing.

Stage Two: The Escape Hatch

Let's say you've started. You've taken some steps, maybe made your first sale or landed your first client. Things are moving. And then they get harder than expected.

A tech issue you can't figure out. Posts that aren't getting traction. An outreach message that goes completely ignored. And in that moment, the voice comes back. "See? You're not cut out for this."

This is the escape hatch moment. And it's sneaky, because people don't usually announce they're quitting. They just slow down. They say they're pausing to rethink or waiting until life settles down. But really, they've hit that first wall and taken the detour instead of pushing through it.

Every meaningful side hustle hits that wall. Not just once, but over and over again. The best thing you can do is commit before you're tested. Before you launch, decide how long you're going to give your side hustle regardless of the challenges. Choose a milestone or a timeframe. Something that keeps you in the game when doubt inevitably shows up.

Stage Three: The Thermostat Effect

This one is the sneakiest of all, because it shows up when things are finally working.

Someone asks you to collaborate, a podcast invite lands in your inbox, or an opportunity shows up that could truly move the needle. And instead of jumping at it, you drag your feet. You don't return the email. You tell yourself you're not ready for that level yet.

What's happening here is described in the work of Dr. Maxwell Maltz in his classic book Psycho-Cybernetics. He explained that we all carry an internal self-image, like a mental thermostat, that sets the limit on how much success we think is okay for us. When life starts to exceed that setting, our subconscious tries to pull us back to where things feel familiar. Not necessarily where we're happy. Just where we're used to.

Recognizing the pattern is the first step. Just being able to say, this is my thermostat, not my reality, can break the spiral. Then say yes before you feel ready. Most of the people you admire said yes before they were fully prepared and figured it out after they committed.

So What Does This Mean For You?

Self-sabotage is old wiring, mostly laid down in your earliest years, running a program you never consciously chose. And once you can see it for what it is, you have the power to do something about it.

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