How to Be Your Own Boss (& Ditch Your Day Job)

These tips come from over a decade of coaching freelancers, side-hustlers, and solopreneurs. Let’s dive in!

Tip 1: Start on-the-side

If you spend a lot of time daydreaming about being your own boss or listening to podcasts about starting a business, it can be tempting to just quit your job and “make it work.”

But unless you have a huge nest-egg to draw on for a few months (or years) while you get your business running smoothly, quitting your job may not necessarily be the best option.

Yes, it works for some people to just quit and work from home, cold turkey. But for many others, they too-quickly run out of money, can’t earn money fast enough and then can’t pay rent or put food on the table and go running back to their day job.

Instead, I recommend you start a side-hustle first.

My business, which I now work from home running full-time, started as a side-hustle. I built it up a few hours a day for over seven years. When the moment was right, I finally took it full time in order to be my own boss.

There are a few key reasons it’s a good idea to start a side-hustle before taking the leap. Here are a few:

• A side-hustle will test your dedication to running a business. If you don’t have the drive or passion to run a side-hustle, you won’t have the passion to run a full-time business.
• A side-hustle will help build up your financial runway. In order to build a smart business, you’ll need some cushion. Use funds from your full-time job and side-hustle to build up some savings before taking the leap.
• A side-hustle will help you get some traction in your business. Starting a business from scratch can be daunting. Better to do it while you have the safety net of a job than when literally everything is riding on your success.
• A side-hustle will help you develop the skill set you need to run a business. Running a great business is nothing like the work you do daily in your cubicle (unless you’re running a giant department). A side-hustle will allow you to build up your entrepreneurial skillset, management skills, and see what it’s like to work from home.

Tip 2: Pick a simple, low-cost business model

In order to put a business idea into motion, you’ll need to sell a product or service. That’s just simple business.

If your goal is to be your own boss quickly, one fast way to get there is by picking a simple, low-cost business model like freelancing, consulting, or otherwise hiring out your own services and expertise.

If you’re a designer, writer, developer, artist, or otherwise creative, you already have the skill set you need to be your own boss and work from home.

With a laptop, some basic supplies, and some hard work, you can begin to find potential clients for your business, and become a freelance writer, designer, developer, or hundreds of other options depending on your skillset.

You don’t have to find investors with a lot of money, write up a 100-page business plan, get a degree in management skills, or lease an office in order to be a business owner or be your own boss. For some business ideas, you don’t even need money to get started depending on the product or service you offer.

Here are a few questions to ask yourself when determining if your business model is a good idea:

• Can I start this business idea with equipment and assets I already own? Do I have the technology and tools I need to start this business from home today? If not, how much will I have to spend to be up-and-running?
• How much will it cost me today to start this business idea? Can I begin operating my business today without making a huge financial investment?
• How quickly can this business start generating cash flow? How long until I actually earn money from this business idea? (The quicker, the better.)

Tip 3: Quit when the time is right

When I was unexpectedly let go from my day job (along with half the company I was hired by only a few months earlier), I decided it was time:

I was finally going to be my own boss.

After a few weeks of working for myself, I started wondering: “Why didn’t I do this a LONG time ago!?”

Being my own boss has literally been one of the best things to ever happen to me. But without the push of getting laid off, I might have found myself working for someone else… forever.

That’s a scary thought.

But I’ve also met people who jump too soon — assuming that since they hate their job, they must be cut out for self-employment and ready to work from home even though they have no idea what product or service they could offer. 

That somehow, they’ll make a lot of money working for themselves. 

It rarely works that way.

That’s why it’s critical that you quit your full-time job when the timing is just right. Not too soon, but not too early.

How can you predict the right timing? Here are a few ways:

• Consider quitting when you have enough financial runway. For some people, a healthy financial runway amounts to three months of cushion. For others, it’s two years. Considering what we all went through this past year, Ramit recommends a year’s worth of cushion (up from six months before COVID). 
• Consider quitting when your side-hustle reaches a revenue goal. Again, this comes down to personal preference. If you’re making as much or more at your side-hustle than at your full-time job (putting in a fraction of the hours), maybe it’s time to take the leap.
• DON’T consider quitting when you have a bad day at the office. Bad days are just part of life. Having a bad day at work is not a reason to quit your job and become an entrepreneur (unless everything else is in order).

Tip 4: Just start!

Finally, my best advice to you if you’re tired of working your day job and want to be your own boss is to just get started.

Most people in your shoes do far too much reading articles, listening to podcasts, watching YouTube videos, developing your skillset, and daydreaming.

You’ll never be your own boss that way.

The only way you’ll ever be your own boss is to take action. Even if it’s something small — like attracting your first potential clients — it can lead to eventual huge gains and put you on the path to a successful business and a Rich Life.

So just start. Before you read or listen or watch another piece of advice, go do something.

Here are some simple, quick wins you can tackle today if you’re determined enough:

• Create a simple portfolio to show off your work and share that you’re “available for hire” on your social platforms.
• Draft up a simple one-page business plan to kick things off right.
• Try any of these 6 ways to get your first client by the end of the week.
• Borrow one of these best business ideas that almost anyone can start online.

You’ve got this. Before you know it, you’ll be packing up your cubicle, leaving your full-time job behind and you’ll be your own boss!