The Company Man's Guide To Starting a Side Hustle – Confronting Your Objections

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It’s a rare man that doesn’t – at some juncture of his life – stop to question how things might be different if he worked for himself. Even a man who loves his job occasionally wonders what it might be like to strike out on his own and follow some crazy, half-baked notion.

Self-employment is a dream held by many men but acted on by few.

The reasons for this are many, but from my vantage point, most of the reasons practical men decide never to give themselves a chance to start their own side hustle is because much of what we learn about it – at least in The U.S. – comes from television shows, movies, and the media rather than people who actually run businesses.

In my short life so far, I’ve run four different very-small-businesses (I call them micro-businesses) and I can say, without doubt, that the way they came to be do not match any fairytale seen on TV.

They were small. They were incredibly cheap to start. And, to most people besides me, they were boring! No fancy business models, sexy offices downtown, or intriguing business cards – just a product or service that people wanted.

If you’ve ever entertained a dream like this yourself, I argue that most of the objections you have to just getting started may not be actual objections at all. Instead, they may be objections to what you think you have to do start something on your own.

The truth may be quite different.

Time to Confront Your Objections

In my experience so far, many men have three main objections when it comes to starting their own side hustle. Ask yourself if one (or more) of these complaints is what’s holding you back.

  1. Starting a business takes a lot of time, and I don’t have any.
  2. It’s expensive to start a business, and I don’t have the cash available.
  3. I don’t have a good idea for a business.

If any of those complaints come to mind when you think about starting a side hustle, then you’re in luck right now because we’re going to systematically debunk all three of them.

Let’s get started.

I don’t have the time to start a side hustle.

Creating a business from nothing is truly a labor of love, and one that takes some commitment. In fact, I don’t know anyone who’s started a business and found that things went far easier or faster than they expected.

If you have a demanding job, a family, a life outside of work, or all of the above, this is a real concern. Where are you going to find the hours and hours it takes to create a meaningful income with all of these commitments?

The truth is that you will have to make some changes to how you use your time, but probably not as drastically as you think.

Here’s the good news: A new business only demands a lot of time if you’re attached to the idea that it must be built quickly.

In the book, Outliers, Malcolm Gladwell talks about the 10,000 hours theory – that almost anyone can master a skill if they dedicate 10,000 hours to it. The same is true for your side hustle. If you put in enough hours – into the right places (we'll get to this later) – then you can build a successful side hustle, too.

The rate at which you put these hours in is up to you. Yes, if you go slower, then it will take longer. But compared to your other option – doing nothing at all – what’s the hurry?

Here’s the tried and true technique I use to put the necessary time into any new project without overwhelming myself:

Set aside 20 minutes – no more! – every single day to work on your project, and protect those 20 minutes with everything you have. Never let anything get in the way of this time.

This does two things:

  1. It sets the habit of working on your project a little bit every day.
  2. It gets you started each day, and you usually end up motivated to work much longer.

I’m too broke to start a business.

A micro-business, done right, should rarely cost more than $100 to get started. When you’re starting a business, the easiest thing to do is think about all the things you wish you had that would make running it easy and enjoyable – an office, lots of expensive electronics, maybe a few employees or expensive services that automate pieces of your business.

The funny (and sad) thing about all of these business “necessities” is that they are – at least in the beginning – much more effective at destroying a business than making it successful.

Why? Because these are the fun and sexy things about running a business. They’re the status symbols you use to tell others, “Hey, look at me. I have a business!”

They distract from the real important part of running a micro-business: making money. And, just like keeping up with The Joneses will probably get your family in financial trouble, it will jeopardize your little business, too.

We all love to hear stories about the risk-takers with a dream that sold everything they owned, took out massive loans, and started the “next big thing.”

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