I get it. You want to start your own business.

And taking that first step is scary as hell. You have worries. You have doubts.

What if you fail? What if that failure costs you everything?

But it doesn’t have to be as risky as you might think.

Today, I’m going to show you actionable strategies that will allow you to overcome your fear and start the business of your dreams.

And no, this isn’t going to be another mindset lecture or a fluffy blog post about the “Top 5 Ways to Think Yourself to Success.”

This is a call to action.

So let’s get started.

Passion vs. Practicality: The False Dichotomy

Let’s talk about “pursuing your passion” for a second.

Why does that phrase conjure up the romantic image of someone who risks it all at a chance to win big?

Because there’s an unhealthy and false dichotomy we’ve allowed to become popular rhetoric in America:

That you can’t have enthusiasm for your work and remain practical.

That fallacy is what I like to call “The Trap.”

At the beginning of my career, I fell for it. Hard. You might buy into the idea yourself.

Maybe you’re a member of the “follow your passion” crew. Do you believe that if you just chase your dreams the money will come?

Or maybe you’re the down-to-earth type. Do you pride yourself on being realistic or say things like “work isn’t supposed to be fun, that’s why they pay you for it?”

If you found yourself nodding along to either of those… you’ve fallen for The Trap.

In reality, a wannabe movie star that moves to LA to find their breakout role is probably going to end up waiting tables.

And the college graduate who reluctantly pursues an engineering career even though he hates numbers is going to struggle to be happy.

But those aren’t your only options.

Instead of sticking it out at a job you hate or rage quitting to be a traveling poet, I present to you: The Middle Way (not the Buddhism one).

The Middle Way

Okay, it’s a little like the Buddhism one.

There’s a sliding scale between every two extremes.

Indulgence and self-discipline. Honesty and tact. Ambition and gratitude.

Passion and practicality are no different. The key to a great career is to find a balance between them.

When you take the initiative to start your own business, you have the opportunity to set yourself up in that sweet spot.

Because entrepreneurship is the perfect combination of:

      High income potential
      Freedom and flexibility
      Room to pursue your passion

For example, let’s say you get excited by music and are pretty talented.

If you’ve fallen for The Trap, you might think that your only choices are to:

      A) Risk it all to go pursue your dream life as a rock star
      B) Settle for playing guitar on the weekends in your garage

But there are so many options in between! You could:

      Give guitar lessons in your evenings after work
      Write an album and build a following on YouTube
Create a course for novice players and sell it online

You owe it to yourself to find your Middle Way.

Think of all the ways that running your dream business would improve your life.

Imagine the pride you would feel when someone asks what you do for a living.

Think of the joy you’d get from being compensated for doing something you love.

Picture the freedom of never having to ask anyone for permission.

I want that for you.

But it’s not that simple, is it?

If it was, you would’ve branched off on your own already.

Why is it so difficult to start your own business? What’s holding you back?

The Real Reason You Haven’t Started Yet

If I had a dollar for every time I heard someone say they wanted to start their own business, I’d be financially free by now.

So why do so few people follow through? Why haven’t you (yet)?

Here’s what you might tell people when they ask about it:

      You can’t come up with a good idea
      You don’t know how to get clients
      • There’s not enough time in your schedule

You might even believe those are your real reasons. But they’re not.

What’s holding you back is the risk.

The risk that you’ll fail… and that the consequences will be devastating.

Maybe you’re afraid of being embarrassed, losing your current job, having to go into debt, or blowing all your savings.

Whatever they are, your fears are what hold you back. Think about it this way:

What’s something else people find exciting? Something more physical, with more obvious repercussions.

Let’s take mountain climbing as an example.


An Extended Metaphor

There are a lot of barriers to entry with rock climbing.

For one, it’s extremely hard work. You need to build some serious strength to hold your body up with just your fingers and toes.

It also requires a lot of skill. Because even a weightlifter with bulging muscles is going to lose to an experienced climber in a race to the top.

But that’s not what stops you from climbing a giant mountain.

You don’t climb mountains because you don’t want to fall off and go splat.

You have a (probably healthy, in this case) fear of failure and the obvious consequences.

…but what if you could grow a pair of wings?

Forget bringing climbing gear. Ropes can snap, nails can slip, and harnesses can break.

But if you could fly?

That would take some of the edge off, wouldn’t it?

Imagine how much more casual people would be about scaling giant rocks if they could glide to the ground when they made a mistake.

(Ignoring the fact that they could simply fly to the top in the first place)

The same principle holds when you want to start your own business. 

Don’t just bring metaphorical climbing gear for the challenge. Before you start your climb, build yourself some wings so that even if you fall off the mountainside, it’s impossible to go splat.

I’ve stretched that metaphor to its breaking point, but you get the idea.

Make your plan to start your own business as foolproof as possible.

Here’s how.

3 Strategies To Start Your Own Business

I’ll let you in on a secret:

Most successful entrepreneurs build their businesses without throwing caution to the wind.

They don’t leap in headfirst. They wait until it makes sense, like when they:

      Have enough cash to go without income for many months
      Can cover their expenses with their business profits
Can’t keep up with client demand without quitting their day job

Only then do they switch over to pursue their entrepreneurial ventures full time.

Here are three time-tested strategies that you can steal and use to start your business without fear.

      1) Moonlighting
      2) Reverse Moonlighting
      3) The Comfortable Cushion

1) The Moonlighting Strategy

If you have the energy and the time (you’ll need both), this is probably the safest way to build your business.

It’s also (usually) the slowest.

The idea is to work a full-time job that powers your finances while you hustle for yourself in your remaining hours.

Zach, the owner of Four Pillar Freedom (4PF), is my favorite example of someone who used this strategy with great success.

Up until 2019, Zach worked full-time as a data scientist. 

Much like myself, he wasn’t a fan of corporate American life. 

Even though he enjoyed working with data, his workdays were often filled with everything except that core function.

Meetings, paperwork, performance reviews, status updates…

I sympathize. You probably can, too.

So he quit. Now he makes a living building profitable websites.

And 4PF recently pulled in over $7,000 in a single month.

But he didn’t get there overnight. And he didn’t jump into his business face first.

Over two years, he built up his website during his evenings and weekends. Eventually, his revenue through ads and affiliate sales covered about 80% of his expenses.

Since his monthly spending was only about $2,000/month, that meant he only needed to earn an extra $400/per month after quitting his job to break even.

Sound doable to you? It does to me.

2) The Reverse Moonlighting Strategy

Moonlighting can be a great strategy for those with:

      A high paying full-time job
      Few other demands on their time
Patience and an abundance of energy

But not everyone can force themselves to put in an extra 2 to 4 hours in the evenings on top of a full-time job.

Maybe you have familial responsibilities, despise your current career path, or are just anxious to focus on working for yourself.

All of those are understandable.

If you’d rather focus most of your working hours on your business while retaining financial stability, I recommend employing the Reverse Moonlighting Strategy.

In essence, you’ll prioritize your riskier venture (or personal time) and lower the hours you work for your more reliable income.

For example:

Moonlighting: Work for an employer from 9:00 am to 5:00 pm and work on your business from 7:00 pm to 9:00 pm.

That’s a 10-hour workday, with just 2 hours a day spent on your own business.

Reverse Moonlighting: Work for yourself from 8:00 am to 1:00 pm and work part-time gigs for an employer from 2:00 pm to 5:00 pm.

That’s an 8-hour workday, with 5 hours a day spent on your business.

You’ll probably be sacrificing some cash flow in the beginning, but your business will grow a lot faster.

And if you have personal concerns that demand a lot of attention, or just prefer a better work-life balance, you’ll be able to squeeze that in too.

3) The Comfortable Cushion Strategy

But what if you don’t have the time to pursue two demanding career paths at the same time? 

Maybe you have a very time consuming full-time job and your young children take up all your evening hours.

Don’t worry. You can still safely start your own business.

Instead of working two jobs simultaneously, work hard for an employer for a few years. Use that time to squirrel away a big chunk of change.

That cash will fund your lifestyle when you start your own business.

My own story is a good example of this.

I left my gig as a Certified Public Accountant earlier this year.

It was a steady paycheck, a solid career path, and I’d worked hard to get to where I was.

You might think I’m crazy to give up a full-time job at a time like this (“In this economy?!”).

But the truth is… the job kind of made me want to put my head through a wall. I needed a change.

And, more importantly, I had been working towards self-employment for years using the Comfortable Cushion Strategy.

Despite living in sunny (and pricey) Southern California, I manage to keep my expenses low. I spend a little under $2,000/month, most of which goes to rent.

Even with a fair but unremarkable income (roughly $70,000 a year), that translates to a savings rate of over 50%.

Because I kept such a high percentage of my earnings, I started to build up meaningful savings very quickly.

Earlier this year, I realized that I had enough to go without income for 5 whole years if I needed to.

That cushion gave me the confidence to strike out on my own.

Closing Thoughts

I want to leave you with some words from the man who inspired me to write this post: Jacob McMillen.

At the end of his stellar (and free) guide to starting a freelance writing business, he wrote something that resonated with me:

“I can fail 5 times and succeed on the 6th before most people will even make their first attempt. 

You will ONLY succeed in this business if you are willing to go, go, go, and learn along the way as you make your inevitable mistakes.”

Like I said in the beginning, this isn’t another mindset post.

This is a call to action.

Start saving more aggressively. Start working on your business in whatever free time you have. The clock is ticking, and you can’t wait forever.

Are you going to just nod at my advice and keep putting things off? Or are you going to take action?

Let me know what steps you’re taking to start your own business in the comments below!

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