The Wethos Collective -- Blog

How To Self-Reflect For Successful Self-Employment

Posted by Vivian Nunez on Oct 18, 2018 4:51:52 PM

Whether you’re debating switching from 9-to-5 to full-time, being-your-own-boss kind of work, or graduating from college and knowing that traditional isn’t for you — that first gut feeling should only be considered the beginning of the conversation you should be having with yourself.

The question “do I want to be self-employed?” is often layered in a way that can be neglected when you’re chasing “the grass is greener where there are no annual reviews” feeling.

Conversations with my friends on the topic of self-employment are often relegated to me and with pointed looks I’m asked my opinion on whether I think they would be a good fit for the specific career track. Over time I’ve learned that the best thing I can do in those moments is to turn the conversation right onto them.

I’m not able to determine if a person is or is not fit for self-employment because every person and work style is different. Since I started working for myself, what I have found, is that there are certain questions that will help you determine if right now is the right time for you:


Question #1: Why do I want to be self-employed?

There is no wrong answer to this question. Reasons can vary from wanting to travel and work simultaneously to wanting to challenge yourself into being your own boss. Either way, what this question does do is that it helps you clearly note the why behind your career move. On harder days, being able to refer back to this why will be your life raft.

Question #2: Do I have enough work lined up to financially support myself and my lifestyle?

Or, an alternative question is, do I have enough of a pipeline to know that even if I don’t have work right now, I will have work within the next few weeks or months?  The key behind this question is to ensure that you aren’t just chasing a momentary rush of adrenaline. This question will force you to stop long enough to note where your income will be coming from and how that pairs up with your monthly expenses.

Question #3: Am I ready to handle accounting?

On the note of expenses, a huge question you should be asking yourself before you become self-employed is whether you’re able to handle accounting on your own or hire someone else to do it for you. After much deliberation and one too many installment agreements with the IRS, freelancer Ashlee Christian decided that it was finally time for her to hire a professional to math and help break down her tax liabilities both as a W2 employee and a 1099 freelancerNavigating taxes, how much you should be saving, or transferring over retirement savings (particularly if you worked in a 9-5) are realities of being self-employed. Quarterly, as a freelance individual you’re reminded how amazing accountants are for making it as easy as possible to navigate estimated tax season. Wethos has noted some great tips on how to manage your freelance finances.

Question #4: Are you willing to learn about your work style?

Often we operate under the assumption that we all have one fixed work style, but once you dive into working for yourself, you learn that this isn’t true. Everyone works best and different hours of the day and in different scenarios. Some work exceptionally well at co-working spaces, while others much rather hunker down at a coffee shop or on their own comfy couch. Asking yourself this question will help ensure that you’re giving yourself room to honestly figure out the best places you actually prefer to work, what times work best for you, and what systems you need to put in place to track your time and to-do's.

Question #5: What’s stopping you from jumping now?

I am four years into being self-employed and some days I still get questions about when I’ll get a traditional job. There will never be a perfect time to make the jump into working for yourself, but there are times that work better than others. It’s important to take stock of where you are in your 9-to-5 and the realities that may be standing like roadblocks between you and your dream of working for yourself. If the biggest reality is that you’re telling yourself you can’t do it, admitting that is the first step to actually figuring out how you can do it. Baby stepping your way to the big decision will help ensure that you feel confident every step of the way.

These five questions are just starting points to your potential freelance journey. It’s no one’s right to talk you into or out of the career lifestyle that makes the most sense for you. The hope is that with these five questions you’ll have a better introspective  realization of where you are and where your career ambitions may rest.

Being your own boss is never easy — it takes time management, lots of patience, and understanding your work style and how it changes. Nonetheless, for all the ways that a learning curve must be applied, the art of working for yourself is always fun and in the right way, deeply aligned with where your heart and passions may be.

Put your passion and professional network to work at Wethos Teams.

Topics: Freelance, Freelancing, Get Started, Tips/Tricks