Dreaming About Self-Employment? 5 Practical Questions to Consider

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Want to be a Self-Employed Military Spouse? 5 Questions to Ask Yourself Before Diving into Self-Employment

I never wanted to be an entrepreneur. Even calling myself that now somehow seems false, although I have clients I write for and run a blog that has unwittingly become a small business. I like the safe, sure bet. I don’t take crazy risks.

And then I got married and became a military spouse. The first months of our marriage, I experienced a loss of self-worth that I hadn’t expected—I had given up my job and while I had secured an online teaching position at a prestigious university, I was new and only teaching a small amount of credits. My paycheck was woefully below poverty. I felt worthless and had a bit of a crisis of identity. You know, really stellar things to experience as a newlywed in a brand new state and town. My poor husband probably thought I had lost my mind.

But as the months went on, I started receiving requests—would I write for other businesses and organizations? I said yes. Two years later, I’ve built a client base and write for a variety of publications.

That very small business has helped my husband and I pay off loans, save for a trip to Europe, and sock away extra money into our IRAs. It’s helped me feel more empowered again, and I’ve created a career that I can take anywhere with me. That’s pretty exciting, too.

Want to Be a Self-Employed Military Spouse? 5 Questions to Ask Yourself Before Diving into Self-Employment

If you’re like I was—on the fence about the possibility and practicality of self-employment—there are a few questions you can ask yourself as you get started and do a little soul-searching:

1. What am I really good at?

Military spouses are often jacks-of-all-trades. We’ve spent time doing different things and usually have resumes that are a patchwork quilt of experiences and careers. But what are you really good at? What can you offer as a service or a product that others would willingly purchase?

2. Can I sustain self-employment?

Last year, I launched a military-themed embroidery shop on Etsy… and closed it after about a month. You see, I love embroidery. Love it. But I realized that producing the same design over and over again sapped the fun for me. It took a craft and hobby that I enjoyed and turned it into a chore.

It was a valuable lesson: there are some things that I’m just not cut out to be… and an Etsy shop owner is one of them. How about you? Are you sure that the thing you want to jump into is something that you’ll be able to pursue with excitement and enjoy doing?

3. Is this a good time?

It might be that there’s no such time as a good time, but there are some exceptionally bad times to start working on being self-employed.

If you’re dealing with personal or family illnesses, for example, you might want to wait to launch. If you can’t spend the time that you know you will need to in order to make your business viable, you might want to hold off too. Know your situation and your limits before greenlighting this new adventure.

4. What mentors do I have or could I tap?

Mentors are so important when you venture into self-employment. They can offer valuable insight and inspiration as you begin feeling your way along this new path.

Online, it’s easy to find groups who are dedicated to supporting each other around the particular field you’re interested in. You might be able to find in-person groups as well. Having these connections are especially important if your business will thrive on referrals or if you provide certain services in a specific niche. Don’t underestimate how powerful mentors and others in your field can be for fueling your self-employment success and solvency.

5. Can we sustain a financial loss?

For me, I sell my time and my writing. I haven’t had to sink money into anything but incidentals: a website layout, hosting, business cards. You get the picture. Shuttering my business would mean a loss of a few hundred dollars—a loss that our finances can absorb.

If you’re going to sink much more into your products—for example, handicrafts—make sure that a failure will not ruin your family’s budget or finances. And if you think they might, have a contingency plan so you’re able to side-step disaster.

As you contemplate self-employment, remember that in all likelihood, you’re not going to be wildly successful at first. You’ll have to grow your clientele. Give yourself the room and the forgiveness to make mistakes, learn from them and grow.

Be ready to feel frustrated and completely overworked with little return on all of your manpower for some time.

But also work toward the first paycheck, sale or positive feedback—it’s one of the best feelings which makes the tough stuff and self-doubt on the self-employment journey worthwhile.

If you’re self-employed, how did you decide that self-employment was the right decision for you?

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