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How to Be Your Own Boss

Be Your Own Boss
Table of ContentsUpdated Apr 15, 2021

Almost everyone has considered leaving their day job at one time or another. Working seemingly endless hours for someone else, knowing that you could do things better and faster on your own is incredibly frustrating.

We’ve all been there.

Do you feel like you have what it takes to be your own boss? It sounds good in theory, but making a huge change from a steady career to working for yourself is not something to take lightly.

Make sure you know the ins and outs of what goes into self-employment before you take that step. There are great things about it, but there are also some drawbacks to consider. As long as you are prepared, the choice to be your own boss may be the best decision you ever make.

Here’s the breakdown on what it takes to be your own boss and how to start taking charge of your own career.

What you should know before becoming your own boss

What goes into running a business? The decision to be your own boss has to be about more than just running away from a job you dislike.

It should be about the best path for you.

Will working for yourself be a good fit? The only way to know is to dig into what that really looks like. Here are some pros and cons to self-employment.


1. Flexibility

One of the best parts of working for yourself is the chance to set your own hours. As a freelancer, you can work when it suits you, instead of on a rigid schedule. This is a particularly great fit for students, parents, caregivers, or anyone who wants to work at non-conventional times.

Sure, there are still meetings you’ll have to work around other people, and some clients need you to be available to communicate during traditional office hours, but you’ll have the freedom to set the boundaries that work for you.

2. Make what you’re worth

As a freelance, you get to set your own rates and negotiate fees as you see fit. Instead of that nerve-wracking conversation every couple of years where you ask your boss for the raise you know you deserve, you choose when and how your income grows.

You do have to work within a marketplace, of course. But when you set out to be your own boss, you have a lot more power over how much your time and talents are worth.

If you want to make more, you can take on more work or raise your rates. If you want less stress, you can take the pay cut and give yourself some down time. And no decision is final.

3. Varied work

If you see shifting circumstances as a threat, the path to be your own boss may not be for you. At a traditional job, the work tends to be monotonous. After all, you were hired to fill a particular need, and while new things crop up from time to time, generally the day to day work is pretty familiar.

As a freelancer, you’ll find yourself working on a huge variety of things. Every client has a different story to tell, and your skills are going to help them get there. It can be interesting and exciting to try new things and stretch your knowledge every single day.

4. Creative freedom

The minute you choose to be your own boss, you stop answering to anyone else. This means that how you do things is largely up to you. You have to work with clients, but you choose which projects are a good fit, and you advise your clientele on the best way to do things.

Every project won’t go your way, but the amount of creative freedom you achieve through self-employment may surprise you.


1. It’s all up to you

Creative freedom, flexible hours–it all sounds so amazing!

Amazing, yes. Perfect? No.

As your own boss, you are, well, the boss. If you don’t do a task, it doesn’t get done. No one is going to tell you when your work hours are, or help you set internal deadlines, or provide you with equipment and office supplies. And there’s no one in the cubicle next door to bounce ideas off of.

As a freelancer, you have to be incredibly disciplined in the way that you work. And that can be terrifying.

2. Inconsistent income

Setting your own rates comes with its own price tag. When you choose to be your own boss, you’re also the one writing your check every month. Particularly when you are just starting out, there will be times when the money isn’t coming in as fast as you’d like it to be.

This is particularly a problem when you have a family relying on you, limited savings, or a lack of time to invest in your business upfront. Living with an inconsistent paycheck is not for everyone.

3. Lack of benefits

Self-employment doesn’t come with paid vacation, a retirement account, or health insurance. These aren’t the only things that matter in a career, but they are important to most people.

As the world integrates further and further with the gig economy, Increasingly good options are becoming available to address these needs. But when you look at what you could make as a freelancer vs. your current salary, be sure to take into account these very valuable assets, and evaluate the costs of replacing them.

Do you have what it takes to be your own boss?

So, you’ve reviewed the pros and cons, and you still think moving away from your current job seems like a good plan. How do you know you have what it takes to be your own boss?

The quick answer here is, you don’t.

You will never know how you’ll do out on your own until you try it. And it’s easy to get really caught up in an analysis of your personality, your talents, your stage of life, etc., and just do nothing.

But sometimes, you have to jump.

Of course, there are some warning signs that this really isn’t the career path for you. So ask yourself:

  • Are you unhappy at your current job?
  • Do you act like a completely different person at work and at home?
  • Are you getting recognized for your skills at work, but you still feel stuck?
  • Can you sell yourself?
  • Can you hold yourself accountable?
  • Do you have an income buffer?
  • Are you ready to learn new things?
  • Do you have time to invest in a business?

If you can say yes to all of those questions, you’re probably ready to be your own boss.

How to be your own boss in 5 steps

Be Your Own Boss

If you’ve gotten this far, odds are you are pretty determined to make the leap to working for yourself.

So how do you do it?

There’s no right or wrong way to leave the traditional corporate structure and be your own boss, and everyone’s journey looks a little bit different. But I can give you a loose layout based on what I did, and what many of my peers have done. Just remember, it’s fine to move at your own pace.

1. Make the decision

As mentioned above, it’s easy to get stuck when you aren’t sure if you really want to leave your job. The next thing you know, ten years have passed, and you are still stuck at the same company, doing the same things. So before anything else, you’ve got to commit.

2. Reach out to your network

You can’t really become your own boss until you’ve booked a client. In the beginning, the easiest way to do this is to put out feelers to people you already know or have worked with in the past.

Just be honest–let them know you’re looking to pick up some contract work in (insert your skillset here), and ask if they know anyone that needs those services? Odds are, someone will come back to you with a lead.

3. Beef up your portfolio

Some people leave their job and go to full-time freelancing all at once. Others start out with a side gig until they are comfortable with how it is growing.

Either way, as you’re starting out, you may need to take on quick jobs for a lower fee or even pro-bono, just to get some samples of what you can do that are professional quality and ready to show prospective clients. The more amazing samples you have to share, the higher-caliber clients you will book.

4. Narrow your focus

As you gain clients and build up more work, you’ll find out what you’re best at, what you’re passionate about, and what doesn’t work for you. Pounce on that experience and start to build up a specific set of skills that plays to your strengths.

This is now your brand and the direction you should follow. Getting specific seems like it might cut out opportunities, but it actually does the opposite. People who hire contractors are looking for an expert in one thing. Become THE expert in that field, and you’ll have happy clients, tons of referrals, and you’ll be happy too!

Be Your Own Boss

5. Grow

Now you’re ready to do some marketing and build your business beyond your immediate network. You may consider cold pitching, signing up for job sites and services like SolidGigs and paid marketing to get more clients.

Set strong goals and then try things out and see what works. As you book more clients, you can become more selective, raise your rates, and watch your business grow.


That fact that you’re reading this article already says a lot about you. You’re a self-starter, you’re already thinking of ideas to make money outside of a traditional workplace, and you’re ready for something new.

If the pros line up with your life goals and the cons don’t scare you, you are more than ready to be your own boss.

Wanting to get out of a dead-end job? We have all been there. Starting out on this exhilarating/daunting journey? We’ve been there, too. The good news is, Millo has tons of great resources for entrepreneurs of all kinds.

Trust us, you’ve got this.

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Written by Kylie Burgener

Staff at

Kylie Jackson Burgener is a mother of three and a freelance consultant, specializing in public relations, writing and content marketing. She is a cofounder of Measured Melodies, a leveled piano sheet music system for piano teachers and students. She lives in Raleigh, North Carolina with her family.

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Reviewed & edited by Adam Wright, Editor at Millo.

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