Should You Be Your Own Boss?

entrepreneur freelance money time Nov 23, 2020
I love being my own boss but I never thought this is the path my life would take. My parents own their own business and I told myself growing up that I never wanted that. They have been very successful but I also saw how stressful it was weathering up and down markets, being responsible for other people’s livelihoods, and working all the time to make sure everything was running smoothly.
Since starting my business, I have been extremely lucky to work for the most amazing people, set my own schedule, and do work that I find incredibly meaningful. I’ve also had moments where I had to figure out things on the fly, wasn’t sure I would have enough money to pay my mortgage, and worked harder than I ever had before. As our economy continues to shift in big ways, freelancing is gaining traction as a way individuals can find more flexibility in their work and life. In 2019 35% of the US workforce freelanced and that number is only expected to rise. Freelancing, consulting, or starting your own business is incredibly rewarding but working for yourself isn’t for everyone. Here are five ways to decide if going out on your own is the right fit for you.


Check your motivations…hard We all want to make more money. That was definitely a motivation for me when I decided to start my own business, but that can’t be your main motivation because it isn’t going to get you through the tough times. Make sure you love what you are about to do and what it brings you (flexibility, time, freedom, autonomy, and money too). That love is what will get you through the long days of wearing all the hats, working all the hours, and maybe still not making ends meet.

With freedom comes responsibility Many people want to work for themselves so that they can have more control over what they do and when they do it. Flexibility and control over your work and life are one of the greatest gifts of entrepreneurship. You’ll also need to balance this with the fact that you probably won’t be able to be choosy in the beginning in terms of the types of projects and clients you take on. You will also need to understand that, especially if you are a one-person shop, when you stop working the money stops too. That means if you want to take legit vacations you’ll need to plan for that financially upfront.

Big dreams only work if you can execute (or find someone who can) Maybe you have a big dream about a product or service that you’d like to offer the world. This dream nags you all the time. You’ve been thinking about it for years and it won’t go away. So maybe it is time to do it. Big dreams make the world turn, but only if people can bring them to fruition. Spend some time thinking through all of the things that it will take to turn your idea into reality. You don’t need to be able to do all of these things yourself, but you need to be realistic about what they are and, if you can’t do them, who will.

You’ll be in charge of the not-so-sexy things too Isn’t it nice when you get that paycheck in your account and it has already been taxed, your 401K has increased, and your company has even covered life insurance? What about when that nice HR person reminds you of the deadline for open enrollment? Or, remember that time a client sued your company but the liability insurance handled it? These are just a few of the things that you’ll now be responsible for once you’re out on your own. There are tons of resources out there to help you manage all of these things as a freelancer, consultant, or small-business owner, but ultimately the responsibility for them will be on you.

Plan to be (or get) good at more than what you’re an expert in now You are a great — fill in the blank — graphic designer, coder, civil designer, etc. That is awesome. The world needs you and your unique skill set. But unless you are also a marketing expert, project manager, business strategist, website designer, HR expert, accountant, and lawyer— all at the same time — then you’re going to have to learn some new things and wear some other hats. Now, I’m a big believer in delegating / hiring experts when that makes sense, but chances are you won’t have the funds to always do that. There will be times when you need to roll up your sleeves and learn new things in order to keep the lights on and the doors open.

You might think I’m trying to discourage you, but I promise I’m not. Working for myself is one of the greatest gifts of my life. It saved me on so many levels and has given me a pathway to a fulfilling life that I would have not been able to find otherwise. But the truth is, it isn’t for everyone, and I’d rather have you go in eyes-wide-open to what it entails instead of being blindsided. When in doubt, dream big and trust your intuition. All of the things above are true and should be taken seriously and they are all solvable if being your own boss is the right path for you.

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