4.3 million Americans quit their jobs this past August alone — the highest monthly resignation numbers in two decades — and the data signals a tectonic shift in what professionals want to do next in their careers.

Remote work is the future. Workers now know this, and much to the chagrin of employers, these workers are leveraging these circumstances to their advantage.

For millions, the perks that come with working remotely are so compelling that if they can’t land a remote job…. they’ll even try creating one instead.

3 Ways Smart, Ambitious People Sabotage Their Online Moneymaking Dreams - Post Outline

Online entrepreneurship is exploding

And I don’t see us going back to the way things used to be. People have now realized that wielding the internet well can replace your weekly salary and then some, and as a result millions of educated, successful professionals have become creator-curious — even if it means potential mental health risks (NYT friend link).

I’ve been at this for 7 years now, and I’ve worked with hundreds of entrepreneurs and employees alike. In my experience, there’s a pattern that comes up again and again when smart, ambitious people try to take the leap into entrepreneurship.

Actually… there are 3 patterns.

Let’s go through each of them now.

#1: Refusing To Look Bad

One of my favorite quotes is from LinkedIn founder Reid Hoffman. He says:

“If you’re not embarrassed by the first version of your product, you’ve launched too late.”

Smart, ambitious people struggle with this — and I have a theory as to why.

Growing up, perhaps you were near or at the top of your class academically. Or you were very good at an extracurricular activity or a certain sport. Perhaps this excellence earned you a scholarship or helped you jumpstart your career.

Being good at that thing becomes a part of your identity. This also happens once you’re already settled in your career, particularly if you’ve spent years climbing a corporate ladder or honing your skills.

You’re a professional. You prioritize quality. At this stage, that mindset — normally an asset — instead becomes your Achilles heel.

It feels scary and threatening to ship something bad, because this would be a reflection on what you do (guilt) and perhaps even who you are (shame). You’re not used to being bad at stuff as it relates to your career or your profession.

So when you go into the Upside Down — where there are tentacles slithering around and there’s fucking fog everywhere — it feels too uncomfortable.

Or you’re bootstrapping it, so you’re trying to learn it all and do it all yourself, which massively wastes time and energy.

It’s become easier to just give up — even though you see people less talented and less experienced than you making it work online.

How to get over it

You’re gonna hate me…

But it’s time to pull a Reid Hoffman and ship something embarrassing.

Blame it on me if you have to — I’m fine with it — but you need to cement the experience of actually finishing what you start.

Too many of you are trying to improve your marathon time without actually ever finishing a marathon first. Finish the race.

A personal example

I’ve offered programs over the years with different areas of focus: Marketing, offer design, email strategy, content creation, and so on.

And regardless of the subject matter, I almost ALWAYS get questions about how to use *this* platform from smart people with incredible knowledge and experience.

I tell them what to do.

And then…. They don’t do it.

This surfaces an important point: A lack of knowledge usually isn’t the real problem.

The real problem is that you’re not willing to look bad. So you hoard information instead and then never implement it. And then you blame the industry.

When you don’t try, you don’t learn, and when you don’t learn, you never develop the business acumen you need to make monetization online work.

Go write something embarrassingly bad today and then publish it. Once the embarrassment subsides, you’ll think to yourself, “Hey, that wasn’t so bad — let’s do it again and do it better this time.”

This is where your ambition and smarts work to your advantage. To leverage that genius, however… you have to finish what you start. 🔥

#2: Only Pursuing A Creator/Influencer Business Model

Influencer culture has created a lot of cognitive dissonance around how to make money online.

Case in point: 86% of Gen Z wants to post to social media for money. Influencers *appear* to have the right mix of ego-stroking audience size and monetization tactics that make it a dream job.

(Many influencers are broke btw — I’ve seen numbers.)

There’s a perception that you need a bazillion subscribers to make a penny online. You don’t.

Even “1,000 true fans” is overrated (Wrote about that here).

There is also a misconception that creators with large audiences are rolling in the dough. In most cases, they’re not.

The real millionaires don’t post Lamborghini selfies. They drive their Jettas to and from Trader Joe’s, take zero photos along the way, and then get back to working on their businesses.

So it’s time for you to make a choice

And that choice is to decide whether you want to be a media company or a service provider.

If you want to be a media company — I say go for it. Do these things in this order:

  • Work to develop the largest and most engaged audience possible. Manufacture content like there’s no tomorrow.
  • Diversify into other platforms once you have a large audience. Example: A podcast. More content means more ad space that can be sold down the line.
  • Sell companies access to your audience in the form of sponsorships or ads.
  • Sell followers access to bigger and better content via paywalls or subscriptions. Example: Patreon, OnlyFans, paid newsletters, maybe some courses, et cetera.

….That’s it.

Then there’s the opposite approach: Being a service provider.

As a service provider, you’re not trying to get in front of a huge number of people. You’re trying to get in front of the right people.

I fall into this category. That means I welcome audience growth, but I’m not super-attached to it; instead, I’m working to connect with the right people.

The steps you’re taking in this approach are to:

  • Manually prospect to get in front of the right people and build your sales chops
  • Create proposals that allow you to command $1,000-$5,000 upfront and $5,000-$50,000 on the backend in the form of long-game retainers
  • Grow an email list that can tolerate being sold to every month when you run promotions
  • Keep your marketing and media efforts niche so that people in your desired field know you are world-class and one of the best in the biz.

This category might sound harder at first. But in my opinion, it’s easier, because you can start monetizing right away.

  • If you want to become a media company or influencer, make that decision now and don’t obsess too much with niching.
  • If you want to become a service provider or have a successful side hustle or freelance career, make that decision now and don’t obsess too much about audience size.

Choose your lane and then use your intelligence and drive to run to the front of the pack.

#3: Having *Too Many* Interests

Online entrepreneurship is incredible because the barrier of entry is very low. Anyone can start a business about pretty much anything — even if they have $0 to start. This makes for lots of options.

…And that’s the problem.

My grizzled consultant side is probably going to come out here. When I got started with working for myself, I consulted brick-and-mortar gyms and fitness studios on marketing.

Owning a gym is intense. If you want to open a gym, the first thing you do is decide you want to open one.

The second thing you do is… take out a business loan for $250,000, because you need all the equipment and free weights and machines on opening day.

You make a big bet on yourself that also greatly limits your options.

And you can’t decide halfway through your buildout that you’re going to become a coffee shop instead — brick-and-mortar business doesn’t work that way.

You have to commit.

This is a good thing. It’s also the thing that is often missing in online entrepreneurship.

Having too many options delays the commitment process.

You’ll never commit, which means you’ll never learn and grow, which means your side hustle or aspiring online business will flounder at best.

An author’s note about “multipotentialites”

Here’s the note: Multipotentiality is bullshit.

A multipotentialite is someone who has many different interests. Everyone has many interests. Mensa is down the hall and to the left, maybe someone over there can make themselves available to tell you you’re special because you’re smart. (Actually, don’t go there, it sounds like a circus.)

We don’t have time for that here — the clock is ticking! We need you to apply your smarts. We need your help and knowledge, and you need to take steps toward this new lifestyle so that you don’t end up working under another shitty boss for ten more years. (People don’t quit jobs, they quit bosses.)

It’s normal and natural to have a variety of interests. That doesn’t mean all these things should be businesses.

Consider that your many interests are keeping you distracted and stunting momentum.

To overcome this… pick one lane and focus on that lane for a minimum of 90 days.

Want extra credit? Stay the course for at least a year. 🤯

You’ll be amazed at how far you can get in a year when you stay focused.

Final Takeaway

You probably already have most of the ingredients needed to make it in online business. The key now is to commit and make your next moves with intention and purpose.

Remind yourself why you want this, build a virtual moat to keep distraction trolls at bay, and you’ll soon find the footing and traction needed to go the distance.

Thanks for reading. 🙏🏼

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