What It Means to Be Your Own Boss

  •    Carrie is a designer and content marketer. She works promoting the Roanoke Region of Virginia and has more than 10 years of media and marketing experience.

The freelance or self-employed lifestyle comes with a lot of perks, but there are plenty of things no one tells you about. You're ready to be your own boss, so here's a look at the good, the bad and the ugly to help you better understand everything that comes with being a solopreneur.

You Are a Business Owner

When you become your own boss, you join 54 million other people who enjoy the flexibility and perks that come from working independently. It's important to understand that freelancing is more than a hobby, it is a small business. Whether you work from home or in a coworking space, part-time or full-time, treating your freelance work as a small business should be a priority.

  • The Good: There aren't a lot of other jobs where you can work from anywhere and make your own schedule. Freelance work allows you to be there for your family or kids when it works best for you.
  • The Bad: Accounting and taxes are probably not your forte, but they are a big part of your business. For every freelance dollar you bring in, you need to account for tax liabilities, keep up with expenses and track overall finances. It can get complicated fast.
  • The Ugly: While you might not report to a boss, you will face a lot of pressure to get things done -- internally and externally. You'll need to master the art of time management and saying no, so that you don't end up working 60 hours a week while still feeling behind.

Do Something You Love

Doing work you love is a major perk of being your own boss. Whether it is making jewelry or writing for publications or designing websites, there are plenty of ways to create a satisfying career.

  • The Good: Work might not seem like such a big deal when you enjoy what you do. You'll have the option to express yourself in the exact way you like, without conforming to other standards or rules.
  • The Bad: Sometimes the transition from hobby to job can strain your relationship with that thing you always loved. Making something that used to be fun into work is a challenge for many people. There are also parts of the job that you might not like, but have to do anyway (or hire out).
  • The Ugly: Not every idea is a good one. Plenty of small businesses fail. Be ready for that risk before you take the dive into a freelance career. You won't have a boss to blame if things go wrong.

Finances Are Part of the Job

Have you ever heard the adage “it takes money to make money?" Starting down the freelance career path comes with expenses. Whether it is equipment or space or advertising, it's likely that you'll need money to get make that initial leap.

  • The Good: Many freelance ventures are fairly inexpensive to start; coworking space (if you don't plan to work for home) is affordable in most markets and you might already have a good grasp on the tools you need.
  • The Bad: You are going to need new accounts for everything -- it's a lot easier when you don't mix business and personal banking. Plus, you need to keep a record of all money that comes in and goes out. Find an organization system early so to eliminate the hassle of bookkeeping.
  • The Ugly: There are always “hidden" costs to running a business for those that aren't well-versed in accounting and tax practices. Think of some of the professionals you may need to work with -- CPA, legal -- and then there are fees to think about, from business licenses to insurance. Talk to other freelancers in your market to get an idea of what these expenses will look like.

You Don't “Live on an Island"

Being your own boss can feel like a lonely business at times. You don't have a team to share ideas with or vent about issues. But you are not alone.

  • The Good: You can create your own network. Get out there and join groups, organizations or attend events that pertain to your field and meet new people. (Make sure to bring plenty of business cards.)
  • The Bad: You will have to rely on others. For some freelancers, the idea of working alone is the draw, but it's not possible to work in a vacuum. You must create relationships -- like it or not -- and manage vendors, colleagues and clients.
  • The Ugly: You won't always have the leverage to make things happen at the pace you prefer. One of the benefits of working for a company is the clout they have when working with others. Working alone, you are unlikely to always garner the same timely responses. Keep working at it and plan for additional time when working with third parties.


So, do you really want to be your own boss? If these ideas don't scare you, it might be time to take your idea and run with it. Freelancing is a choice that's not for everyone, but those who enjoy it can make a worthwhile career and enjoy the flexibility and benefits of self-employment.