Are you curious about the creator economy, but find yourself getting stuck or stopped when it’s time to make decisions?

Do you feel like your brain is buzzing with ideas around how to make money online, leaving you excited — but also unable to focus?

If you’re smart and/or ambitious, online business and the overall creator economy could be your opportunity to flourish.

To do so, however… you’ll have to get out of your own head first. Let’s discuss how to spot some of the most common obstacles to getting started online — and how to overcome them.

Why Smart, Ambitious People Often Struggle In Online Business

Creatives and innovators tend to make up the bulk of the online entrepreneur community. These same people are also highly susceptible to one of the most common and challenging roadblocks to getting started online: Overthinking it.

Smart people usually already know this. And in fact, they like it and often wear their analytical nature as a badge of honor. They see this high level of thinking as what sets them apart from “regular people.”

Overthinking blocks you from making sensible decisions. If the amount of time you spend thinking about something exceeds the amount of time it would actually take you to give it a whirl and move on with your day… you’re overthinking it. Classic overthinking examples include:

  • Thinking about writing a book for several years, when actually writing one would probably take a year or less from start to finish
  • Thinking about launching an offer for several months — and by offer, I mean a product, program, service, paid newsletter, or membership — when actually testing the waters to gauge interest would only take you a few weeks
  • Thinking for months about hiring a virtual assistant for a few hours a week to help you gain momentum or research potential freelance clients, when actually this process can be done in a matter of days using a job boards site.

(Also, ignore everyone who shuns hiring. Y’all sure do eat up that productivity advice every week, but act like outsourcing tasks and buying back your time is sacrilege. Leveraging your time is critical in this industry because it helps you fend off burnout.)

Instead of just taking a step forward to see what happens, you think about it instead. Then you think about it some more. Overthinking is what stands between you and going after your hopes, dreams, and goals in online business.

Overthinking is nothing more than pretentious procrastination.

Almost everything you do as a creator or online entrepreneur requires experimentation, and you can’t run experiments in your head. You have to run them out here, in real-time, in the real world.

So here are some of the most common overthinking demons, as well as what you can do to get yourself back into action.

Overthinking Culprit #1: Having Too Many Interests

If you’re a smart cookie, you probably have lots of interests to keep your sexy faster-than-average brain curious and engaged. That’s gonna trip you up.

Here’s why: Once you commit to one niche, one topic, or one audience to serve, shiny object syndrome rears its ugly head. It’s way, way easier and sexier to go after a new thing than it is to slog through the ups and downs on your current path.

Pick one niche — and then stick with it. We hear buzz phrases about niching all the time in business:

  • “Niche down until it hurts”
  • “The riches are in the niches”
  • “Niche down to blow up”

Niching is a challenge for smart, ambitious people because they‘re too wrapped up in what THEY want to do and making that perfect, rather than serving their audience.

What to do instead

Here’s an idea: Pick one niche and commit to it for 90 days with no detours.

Look at what people in your chosen niche need help with. Then create content and offers that help to solve their problems.

It really can be that simple, but remember: Simple doesn’t always mean easy.

Overthinking Culprit #2: Fear Of Failure

When we were kids, teenagers, and even young adults, we tried new stuff all the time, sucked at it, and moved on.

Example: I played the French Horn as a kid and as a young adult. I wonder how many shitty solo & ensemble performances I gave in which I sounded like a dying cow in front of all my peers. Dozens? Hundreds?

I vaguely recall being embarrassed for an hour or two after a bad performance, then going to the arcade afterward and eventually getting over it. We were resilient back then because there weren’t any expectations.

You’re not failing in online business because you’re not good enough or smart enough; you’re failing because you are unwilling to look bad. Or you’re unwilling to look bad long enough to get over the learning curve and see what works and what doesn’t. You’re intelligent, you’re successful, and you rarely look bad at work. That’s the problem.

I have a decently successful business now, but prior to this I failed loads of times.

First, I tried teaching yoga classes at corporations as a side hustle. Failed.

Then I ignored all mainstream life advice and left my salaried job to try my hand at consulting with a value proposition that wasn’t actually validated. Failed — and lost my whole life savings. That one sucked.

Then I took a shit job at a gym to lick my wounds and reassess. I briefly explored e-commerce on the side — failed.

I liked the funnels and ads parts of e-commerce, though. So then I took a swing at media buying, running business’ Facebook and Instagram ads as a service. Failed.

Then I scooped up a full-time client. Less failure, I guess. Scooped up some more clients on the side.

Then a pandemic came, I finished up with the full time client and was back on my own. I was a little wiser this time and got some traction out of the gate.

Since then, I’ve tried all kinds of things. Some of them succeed, most of them fail.

  • Mastermind — failed.
  • Group coaching program — failed.
  • Membership offer — failed.

But other things began working, and working well. Courses took off for me. 1-on-1 offers took off for me, too. My email list grew to a point where now I have a little ecosystem that is far away from social media, which is nice.

My point is….

You have to fail often and persevere in order to find your sweet spot in the world of online business.

You also have to think like a scientist – a lot. Just because YOU think your idea is great doesn’t mean anyone else will care.

If your side hustle or online business is making less than a quarter of a million dollars a year... You should be throwing spaghetti at the wall every single week and experimenting with what works and what doesn’t.

Hell, I still try new things each and every month. Most of them fail. But some of them work. And those things that work are what pay the bills and give me freedom. I’ll take that over returning to an office any day.

Overthinking Culprit #3: Shunning A Growth Mindset

When you’re smart, it can be easy to think you know it all. This will sink you faster than anything else described here today.

I’ll give an example that’s connected to my own business: Writing. People often think they’re brilliant writers and that they don’t need to work on learning how to write, because they wrote term papers or perhaps a thesis when they were in college.

I was this way. I thought I was hot shit because I placed in a Newsweek essay contest… 15 years ago. “I already know how to write,” I told myself.

Wrong. I have to work on my writing all the time. My writing is a muscle that powers my online business, so I have to look at it and take care of it the same way an athlete takes care of their body.

Warmups. Drills. Fundamentals. Technique. Learning and trying new things all the time. I am never above learning something new about writing. Hell, I buy writing courses and programs all the time and I freaking sell this stuff.

The moment you think you’re good… you’re not. Focus on cultivating a growth mindset and stay the course. Learn new things every day. Embrace challenges. As others begin to sit back on their heels, you’ll continue to improve and eventually break through to the front of the pack.


Online business is wonderful, challenging, stimulating, agonizing, thrilling, lucrative, and brutally honest. And that’s just on a Tuesday.

If you’re smart and ambitious, you more than have what it takes. The key is to get out of your head and into action — each and every day.

Thanks for reading. 🙏🏼

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