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12 Things That Destroy a One-Person Business

by | Jun 12, 2023 | Entrepreneurs

A one-person business sounds better than sex.

The truth is it’s harder than you might think.

I’ve encountered many pitfalls over the last 9 years of doing it. Here are the top 12 so you don’t ruin one of the best opportunities you’ll ever come across.

1. No virtual assistant

I mention this one first because it’s cost me millions.

For most of the last 9 years I’ve had no support. I’ve done everything. It’s taken me to the brink. I’ve had many dark days.

The reason I didn’t get help is because I’m a perfectionist. I don’t believe anyone else can do as good of a job as me. That might be true. But here’s the thing: every task doesn’t need to be done perfectly, especially admin stuff.

I was getting an A+ by answering all my own emails, but deleting emails isn’t an online income stream last time I checked.

In the last three months I’ve experimented with VAs. It’s been a game-changer. Most of my useless admin is gone. Now I have free time to work on my one-person business instead of work in it.

There’s one more reason I didn’t hire a virtual assistant for so long…

2. Limiting beliefs around money

Whenever I interact with anyone online and they say stuff like “I don’t want to buy a $100 course to learn this skill,” I know I’ve met someone who’s not gonna make it.

A one-person business has to spend money to make money.

There’s no other way. Free content and hacks get you nowhere. Amateurs teach them — that’s why they’re free!

I didn’t hire a VA because I saw it as a cost when I should have seen it as an investment. Time is your most precious resource in a one-person business, so if you don’t have a VA you’re literally screwed.

You’ll run out of time, work late nights, and probably end up divorced like many of my other “successful” friends.

You must learn how to see the difference between investments and expenses. And your psychology around money typically needs an upgrade.

An employee mindset will get you nowhere — except back to a soul-crushing desk job earning less than you’re worth.

3. A fascination with business plans

The corporate world teaches us to plan and overthink our way through the workday.

In the one-person business world it’ll be game over if you do this. You have to get money in the door. That’s your #1 priority, not ma$turbating to ideal business plans and perfect customer personas.

You don’t know what you don’t know.

A one-person business grows through experiments. Each successful one can turn into a product or service that you iterate on until you hit the amount of money you want to make.

Don’t get stuck in your home office with your pants down trying to write a business plan. Powerpoint decks don’t earn trophies in this world.

4. Too much focus on the tools

“Should I use Notion or Obsidian for note-taking?”

“ConvertKit or Mailchimp for email automation?”

“Beehiiv or Sub$tack for my newsletter?”

I get emails like this every day from strangers. It’s creepy.

The answer is everything works, so get to work. What tool you choose won’t make or break your business (read that again). What matters is execution.

5. Trying to predict the entire journey

Many wannabe one-person business owners are fortune-tellers in disguise.

They want gurus and coaches to hear their feelings and feel supported. They want a 100% money-back guarantee that their one-person business will succeed before they start.

That’s not how the real world works, pal.

Nobody can tell you if your business will work. Maybe it will, maybe it won’t. A lot of it will come down to patience. Mindset too.

Are you someone who wants something for nothing and believes they should be a millionaire in a year? If so, probably stay away from one-person businesses.

But if you’re someone who’s a little calmer and is willing to trade 2–3 years of time to be free for the rest of your life, then step on up. Join the party. Hi-five your next-door neighbor. Spank their bum. You do you.

6. A jam-packed calendar

I’ve said it already but it needs to be repeated for the folks in the back of the room: time is your most precious resource. There’s zero chance this way of life will work if you’re bad at managing time.

So your calendar says a lot about you and your naughty after-hours habits. The only way to get a clean calendar is to get bloody good at saying no.

Your default answer to every new opportunity or rabbit hole should be “no.” Even better, your default should be to *not* respond.

7. A non-active social media audience

Having people to sell to is so bloody crucial.

I don’t know a single one-person business online that has succeeded without social media. Without the attention of people you’ll never have any leads.

It doesn’t mean you need to become a show pony, but you do need to master the art of giving value online for free. That just means showing people what you know without any creepy hidden agenda.


Choose one social media platform. Post daily there.

Find people who like similar stuff and join forces with them so you can share each other’s content.

8. A Mount Everest-sized ego

Knobheads never get anywhere in life.

If you’re one of those douchebags who like to “flaunt” or “influence” or be rude to people, then forget about a one-person business.

Your customers are attracted to your business because of you. So if that ‘you’ is hurt, broken, and not a nice person — no sales are going to happen. Best to get therapy and then have a go at a one-person business later.

Big egos block people from getting feedback too.

When a customer or email subscriber says something negative they take it personally and have a cry. This world requires thick skin.

You can’t easily be offended, because those who are offended need to be offended more often.

9. Not following the data

Making decisions in a one-person business is easy: follow the data.

Don’t think you know everything. Don’t rely on intuition, or hand-wavy signals from the universe. Or advice designed to oversell you something.

Collect data. Look at likes, comments, shares, and bookmarks on social media. Even better — run surveys to your audience and find out what their problems are. If you really want to make 7 figures online then find out what people’s biggest pains are. Then solve them.

I run manual surveys monthly, and automated ones daily.

That’s how passionate I am about data. And the data always makes me look stupid because I can never predict what people need, even though my fragile ego thinks I can.

10. A lack of testimonials

You can’t sell anything to strangers without evidence.

If I’m seeing you for the first time the first question I have is “can I trust you?” Testimonials help form that bond.

But testimonials are evolving. You need text, social, and video ones. Some of the most powerful are tweet testimonials because potential buyers can contact them or at least see they are real.

Whereas a lot of businesses use fake testimonials or ones from their mates, then wonder why no one trusts them lol.

Testimonials prove you can deliver. So deliver and collect them.

11. Habits with no systems

Many wannabes try to run a business on a whim and a hope.

It doesn’t work. If you ever want to do less work then you’ll need to outsource some of the tasks to freelancers. The only way to do this is with systems, otherwise it’s a huge pile of mess.

A habit is something you try to do regularly. A system is a series of checklists and documentation stored in the cloud that can be shared easily.

I just bought Notion for my business and took all the systems for everything and put them in one place.

Every task has a date, owner, and description of what to do.

It’s so simple a 5 year old could follow it. Heck, my 7 month old daughter could probably work it out.

Systematize or get hives and die.

12. A lack of automation

A one-person business has freelancers who help on an ad-hoc basis.

The only real employee of your business is software. I use Zapier to automate as many little tasks as possible because it’s cheaper than a human and doesn’t need toilet breaks or days off for Memorial Day.

Automate or die trying.

Here’s what makes for the greatest one-one person business in history

You’ve heard what destroys a one-person business. Let’s end on a high and get high on life.

The greatest one-person businesses I’ve ever encountered manage to survive and thrive because they’re built on obsession.

The people that run them are possessed. They love everything about their business. It’s built on passion, purpose, and legacy. They wouldn’t ever want to do anything else. They’re building for the next few decades, not the next 5 minutes.

They don’t have to feel like working. What they do on their day off is what they do on their workday. This is the holy grail.

Build a one-person business around your obsession.

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