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Make the Leap: How to Become Self-Employed Without Risking It All

8-minute read

It’s easy to start your own business right from home, like this self-employed entrepreneur at his desk.
Mariah Bliss

Mariah Bliss

8 June 2020

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When I first decided to become self-employed, I had no savings. No business plan. No clients. And I had bills that needed to be paid ASAP.

So when I took that leap to freelance, it didn’t just feel like a leap: It felt like a freefall into the unknown. And while it ended up working out for me, I wouldn’t recommend taking my approach to anyone who wants to enjoy a good night’s sleep!

Becoming your own boss is definitely scary and requires a leap of faith, but I’m here to give my perspective on how you can dip a toe in the waters of entrepreneurship so you know what you’re getting into.

The secret? Spinning up your business on the side until you’re ready to make that full leap to being 100% self-employed.

I’ll reveal what I’ve learned from my own experiences, as well as the lessons I wish I’d known before I started working for myself.

10 Low-Risk Steps That Can Help You Become Self-Employed

Before we begin, let me be clear: Learning how to become self-employed will carry some risk. Not every business venture is a successful one. Projects can dry up, or you may lose the passion for your business after going at it for a while.

That’s why this article is dedicated to helping you make that lower risk, gradual adjustment to self-employment.

So without further ado, let’s take a closer look at the steps to becoming self-employed.

1. Pick something you’re good at.

If you’ve made the decision to go solo, but you don’t know exactly what you’re going to do, you’ve probably found yourself asking this question:

“Should I do something I love, or should I do something I know?”

Here’s an example to illustrate what I’m talking about. I consider myself to be a writer, both by trade and by skillset. So when I decided to work for myself, it made sense to leverage my writing talents and become a freelance writer.

But maybe you have a skillset that happens to be different from something you love. Maybe you’re an awesome marketer, but you love to make costumes. Or maybe you’ve made your living as an arborist, but you consider yourself a handyman at heart.

It may be tempting to strike out on your own doing your 9-to-5 gig, or just go a different route and monetize a hobby or skill you love. But no matter which option you choose, this is the real question you should be asking yourself:

“Can I see myself doing this for the rest of my life?”

Times are going to get tough. You will come across challenging moments that may make you wish you weren’t working for yourself.

That’s why whatever you decide to do needs to be something you can see yourself doing for the rest of your life — and that makes you happy to picture it.

So if that’s a skill you learned during your 9-to-5 job, awesome! Or if it’s a hobby that can make you money, great!

But regardless of which option you choose, make it one that will not only help you make money, but will bring meaning and purpose into your life.

Because when those challenging times hit, it’s that meaning that can help see you through.

2. Research your market to gauge demand.

No matter how passionate you feel about your future business, it’s going to be hard to get it off the ground if there’s no one out there to buy what you’re selling.

Before you start that journey to become self-employed, take some time to research if there’s a market for your services. I’ve written on how to perform easy market research in the past, but here’s a quick “back of the napkin” exercise that can help figure out if there’s an appetite for your business:

  • Google your business idea and see what comes up in your location. Too few results, and there may not be a market; too many results, and you may face stiff competition when starting out.

  • Check out sites like Upwork, Guru, or Thumbtack to see how many projects are out there for people in your profession. If you want to start your own thing in a contracting field, look to sites like Angie’s List or HomeAdvisor. Lots of projects = lots of opportunities.

  • Ask small business owners in your industry and location if they see demand. If they’re continually turning away work because they’re too busy, there may be space for you to carve out a clientele base.

So what happens if you perform market research and you’re not seeing a lot of demand?

Here’s the thing: Because this is a cautious approach to becoming self-employed, you can always put yourself out there and see if you find clients. You just might be surprised at the untapped demand you find.

And if you don’t, no worries; just head back to step one and identify a skill or talent that might work better for you.

3. Develop your long-term plan.

Starting your own side gig while still working a 9-to-5 gives you the time and space you need to think about what your ideal business looks like.

But that time and space can become addictive. It’s fairly easy to become comfortable getting a regular paycheck while working for someone else, so you may find yourself putting off that leap of faith out of fear.

That’s where a long-term plan comes into play. Create a timeline — complete with milestones — for when you’ll make the move from working for someone else to working for yourself.

For example, maybe you plan on giving yourself one year to work on the side before making the decision on whether or not to go full time. Or maybe you need several clients before you feel financially comfortable enough to work for yourself.

Once you develop that plan, keep accountable to it. That way, you won’t get stuck in a place where you’re not fully embracing your ability to be your own boss.

(Oh, and if you need help creating that plan, check out our FREE business plan template).

4. Get buy-in from the people who matter most.

No one starts a business in a vacuum. So if you have a family or close relationships that may be impacted by your being self-employed, let them know you’re planning on striking out on your own.

Now, this doesn’t mean you should give up if they express hesitation over your self-employment dreams. But it’s a good way to get buy-in and avoid tensions from bubbling over, especially if working solo means you might need to cut back on spending some time with loved ones.

5. Carve out time to devote to your side gig.

The biggest benefit to staying in your 9-to-5 job while striking out on your own is that it minimizes the risk and stress associated with trying to drum up business as quickly as possible. You’re still able to pay your bills, but you’re starting to slowly build your clientele list until you’re ready to make that big leap.

That does mean you’ll have to carve time out from your personal life to devote to starting and building up your business. Whether it’s an hour each day or time dedicated on the weekends, mark down your new schedule and stick with it. Let other people know about your schedule so you can dedicate 100% of that time to your side gig.

One important note: Make sure your activities don’t interfere with your 9-to-5 job. You could get into hot water if you perform any of your self-employment activities during your regular work day, or if you use any of your company’s assets when building your own business. Check your HR handbook to see your company’s stance on working for yourself outside normal business hours.

6. Protect your work ASAP.

When you launch your side gig, you should protect yourself right away with business insurance.

Here’s why: once you start working with or for clients, you could be opening yourself up to risks and liabilities. It doesn’t really matter what industry you’re in — there’s always a risk you could make a mistake that a client sues you for.

And if you’re just starting out on your self-employment journey, that’s a risk you don’t want to take!

Business insurance can help protect your work, even if you consider it to be just a side gig right now. A self-employed business insurance policy can cover the costs of claims resulting from negligence and errors made during your work. Self-employed insurance - particularly general liability insurance - can also cover the costs of claims resulting from property damage.

Quick plug: Simply Business can help you find business insurance policies tailored for self-employed business owners, sole proprietors, and more. Compare free quotes in under 10 minutes to see how your business (whether it remains a side gig or becomes a full-time venture) can be covered!

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7. Start putting aside your 9-to-5 money.

Unless you plan on financing your venture with small business loans when you go full time, consider allocating a portion of your money from your 9-to-5 paycheck to put towards start up costs for your new venture.

Here’s why: starting your own business — even if you’re doing it part-time — is going to require some money. You may need that cash for things like:

  • Invoicing software
  • Business license
  • Business insurance
  • Computer or phone for your business
  • Website
  • Online ads
  • Tools
  • Equipment
  • And more

If you’re able to use part of your 9-to-5 paycheck to cover some (or all!) of the above costs, you’re putting yourself in a much better position for when you finally go full time.

If possible, put aside some money to support yourself and your family during those first few months when you go full time. Hopefully, by then, you should have a large enough clientele base to earn enough money, but your savings can provide a financial cushion in case it takes a little while for your business to build up steam.

8. Take a moment to reflect.

Being self-employed is tough., So as you start building your part-time business into a full-time one, you should pay attention to how you feel. Ask yourself questions like:

  • Do I feel fulfilled by my business?
  • Is it hard for me to find time for my side gig because it stresses me out?
  • Do I get excited thinking about working for myself?
  • Have I developed realistic goals for my own business?
  • Am I really ready for how much this may change my life?

Take the time to reflect on your experiences before making the full-time leap. It’s a small step, but a critical one for helping you jump into self-employment with eyes wide open.

9. Know when it’s time to make that leap.

So you’ve done the hard work. You started building up your customer base, and the demand is getting significant. Maybe you even have a website and a few online ads out there. Whatever you have going on, there’s going to be a point where you’re starting to feel like it’s time to make that leap and go full time.

It’s funny how this moment may happen for you. Maybe you’ll be able to make the decision based on hard data, like you have too many clients to handle part time. Or maybe you’ll just know, deep down, that you’re really, truly ready for this.

Enjoy that moment. It’s a life-changing experience — one that you’ll be able to point back to later in your journey as the “aha” moment when you embraced your identity as an entrepreneur.

And who knows — maybe someday, you’ll be able to use that moment to inspire someone else who’s struggling with the decision to work for themselves!

10. Take a deep breath — you’ve got this!

Being self-employed can be a whirlwind.

On the best days, it’s incredible — you get to set your own schedule, make your own decisions, and build your work around your life (and not the other way around).

But on the worst days, it can be stressful, especially if you’re going through a time when clients might be lacking or you have to chase down unpaid invoices.

No matter what happens, know that you’ve got this. Be open to continually learning and growing as you build your business (our blog can help you do just that!). Protect it and do right by your clients, and never forget to take those moments to appreciate how far you’ve come from working a 9-to-5 job.

Good luck, and keep in touch with how being self-employed works out for you!

Mariah Bliss

Written by

Mariah Bliss

I love writing about the small business experience because I happen to be a small business owner - I've had a freelance copywriting business for over 10 years. In addition to that, I also head up the content strategy here at Simply Business. Reach out if you have a great idea for an article or just want to say hi!

Mariah writes on a number of topics such as small business planning, contractor insurance, and business licenses.

This content is for general, informational purposes only and is not intended to provide legal, tax, accounting, or financial advice. Please obtain expert advice from industry specific professionals who may better understand your business’s needs. Read our full disclaimer

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