4 Questions To Ask Yourself Before Becoming Your Own Boss 💭
By: Office Hours With Kelsey Mulvey
Tags: Solopreneur, Freelancing, Honesty

I don’t say that to throw shade or squash anyone’s dreams, but I have to be brutally honest. Self-starters are a rare breed. They know how to think on their feet, handle uncertainty, and hustle their way out of any slump. On the other hand, some people need the stability and structure of a full-time job — and that’s totally okay! (Having a full-time job doesn’t mean you’re less ambitious or not dedicated to your career; you just work differently.)

When I took the leap of faith almost four years (!!!) ago, I knew that I wanted to give the freelance life a try. I left a full-time position because I wanted to be in the driver’s seat of my own career. That said, I know everyone else’s freelance journey isn’t as deliberate as mine was. Some people feel pressured to become their own boss after getting laid off or moving away from their full-time position. But, before you take that big jump, I encourage you to ask yourself the questions below. Ultimately, the decision is yours — and everyone has different freelancing philosophies. But, I hope this insight helps you understand if being your own boss is for you.

Do You Know What You Want To Do?

Two years ago, one of my friends wanted to pick my brain about freelancing after they were laid off from a job. The catch? My friend didn’t know exactly what they wanted to do. “Maybe a little bit of marketing, I could write, or maybe some social media work,” they said. And, just last week, another person asked me what type of freelance work they should do.

I understand getting laid off is scary, and freelancing might seem like an attainable and immediate solution. Plus, I’m all for doing whatever it takes to support yourself, financially. However, I think it’s so important to understand what unique skills you can bring to the table first. Even if freelancing is a temporary chapter — a necessary step between jobs — it requires a lot of time, energy, and persistence. So, how are you supposed to get clients and thrive if you don’t even know what your secret sauce is?

Instead of diving head-first into the self-starter sphere — which can often feel like the digital wild west — take a beat to find your hustle. If you can’t think of a job that lights you up, you might want to reconsider the freelance path.

Do You Have Your Foot In the Door?

Admittedly, my transition into solopreneurship was relatively easy. You see, I was a professional journalist for years, and often took on freelance work in addition to my full-time jobs. So, by the time I went out on my own, I already had a few clients who gave me steady work. Before you go freelance, think about who you can reach out to for work during those first few months.

Of course, just because you don’t have a full client roster doesn’t mean you should neverbecome your own boss. If possible, spend a few months balancing your full-time job with a side hustle. That way, you can have some financial stability as you begin your self-starter journey.

And, once you’re ready to go out on your own, use these tips for landing your dream client. (Psst…it’s all about networking!)

Are You Self-Disciplined?

Despite being my own boss, my days are pretty structured: I wake up early (well, early on the west coast), send out emails as I enjoy my two cups of coffee, make a to-do list, and prioritize my assignments accordingly. Sure, I’m guilty of the occasional Instagram scroll — I mean, I’m human — but I know how to motivate myself.

Personally, I can’t stand when someone else tries to dictate how I spend my time. (As my own boss, I’m juggling multiple projects at once and have a strategy for getting things done.) But, I realize some people need that structure. They need to have a calendar filled with Zoom meetings, concrete work hours, and a boss to report to on a regular basis. At the end of the day, it’s a personal preference. But, if you fall into the latter category, full-time might be the better route.

Can You Be A Little Selfish?

I became my own boss at the perfect time in my life: I was in a long-distance relationship with my now-fiancé. I didn’t have kids to care for or a mortgage to pay off. And, I was still on my family’s insurance plan. Though I was enthusiastic about being a freelancer, I wasn’t totally sure how it would pan out. (I mean, how could I?) But, I could be a little selfish. I knew that I had the time and energy to fully immerse myself into my work.

Think about your personal responsibilities. Are you supporting other people? Can your savings account support you if needed? How will you and your family receive health insurance? Do you have the freedom to work nights and weekends, if needed? (Let’s be honest: We’ve all been there.)

Breaking out and being your own boss is a gamble. It’s a decision that should not be taken lightly. If you can’t be a little selfish with your time and energy, seek out opportunities with a formal contract and benefits.

Hustler of the Week: Delaney Vetter

What inspired you to become your own boss?

I wish I could say it was an active choice at the time, but it was really a string of tiny choices and circumstances that led me to “accidental entrepreneurship.” I’m a 2020 grad (a.k.a. pandemic grad) and like most people my age, post-grad life became even more unpredictable with a nonexistent job market. I got the opportunity days after [graduation] to get a small freelance role, which grew exponentially. I started getting referrals, and the possibility of pursuing this as a career became a reality to me.

In July 2020, I ended up getting a job offer at an amazing company, but I was so conflicted. My dad said, “You have nothing to lose and you might as well give this a shot while you have nothing else holding you anywhere.” That was when I decided to pursue this self-employed thing seriously and since then, it’s just grown and grown. I never thought being my own boss would be an option this young, so it felt like too good of an opportunity to not try and capitalize on.

What is your favorite part about being your own boss? Least favorite?

My favorite part is not being tied to one place. I haven’t been able to take advantage of this yet, but hoping to soon! Least favorite? It’s really lonely sometimes. I thrive in team settings and around people, so being your own boss and social distancing on top of that has been a real challenge at times.

What’s the biggest lesson you’ve learned since becoming your own boss?

There are so many things I’ve learned over the last year, but something that comes up again and again is not being afraid to say no. When I first started, I felt like I had to work with anyone who approached me. That got me into several projects where I ignored red flags and ended up anxious and unhappy with toxic clients, or taking on things that weren’t what I wanted to be doing.

It took me several months and a lot of late nights and stress to realize that saying “no” was as important as saying “yes.” It wasn’t good for me or for them to say yes when I knew in my gut something wasn’t right. This is something I am constantly working on, but has been a huge realization for me.

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