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Want to Make the Leap from 9-to-5 to Self-Employed? Here’s How to Do It

4-minute read

Mariah Bliss

Mariah Bliss

5 August 2019

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I remember sitting at my desk, tucked in a cubicle, staring blankly at Microsoft Word. The office was quiet, uninspiring, and downright depressing.

Most of the staff members had worked at the company for decades, not because they believed in its mission, but because it was a job—one that paid the bills and was easy to do.

I had to get out.

I began to dream of other career paths. I watched episodes of Sex and the City and fantasized about living out Carrie Bradshaw’s writing career. Why couldn’t I write for myself? Wasn’t my work worthy of being published? And how did Carrie Bradshaw make enough cash to live her lifestyle? (By the way, I still have no idea.)

The seed was planted, but I didn’t actually make the leap from 9 to 5 to full-time self-employment until nearly 10 years later. I wasn’t ready, financially or emotionally. Now don’t get discouraged. For most people, it doesn’t take that long.

And if you know what to do, it’s easy to start sooner.

5 Steps to Make the Leap from 9-to-5 to Self-Employed

  1. First, know if you’re ready.

    The truth is, it shouldn’t have taken me 10 years to go full time. Deep down, I was ready earlier. Here are some signs you might be ready now:

    • You’re dreaming of owning your own business—during your 9-to-5 job.

      As I mentioned, I used to imagine myself pitching to publications.

    • When you’re outside work, you spend free time working on your gig.

      I used to rush home, only to turn on the computer and design my own logo. Nerdy? Yes. Typical of an entrepreneur? Also, yes.

    • You’ve acquired important skills needed to run your business.

      During that 10-year span, I worked under ruthless editors, hired freelancers, and spent time as a marketing manager. That time period gave me invaluable skills that I rely on today.

    • You have your eyes on first customers.

      To make the leap, you don’t have to officially secure a customer, but it does help. Before you go full time, network in your industry and start building a customer pipeline. Is there interest in your product? Is there a need in the market? Find out.

  2. Have a plan for funding.

    If you have a family, sit down and talk about how owning a business will impact finances. Look at your budget. What can you cut back on? Then map out how much money you need to get started.

    Every business is different. As a writer, I just needed a computer. But if you own a landscaping company, barber shop, or you work in farming, you’ll need equipment. For example, my cousin owns a successful maple syrup business in Vermont. And I know he’s taken out loans for equipment.

    Be detailed about your financing needs and make a plan for obtaining funding. If you need a significant amount of cash, you can try:

    • Talking to investors. If an investor buys into your idea, you can get a significant amount of money—and fast. The downside is investors offer funds in exchange for ownership of your company. Depending on how much they put down, you could lose control of your business and its direction.

    • Taking out a small business loan. A lot of small business owners go this route, mostly because it’s simpler and less complicated than dealing with investors. They also want to keep control of their original idea. But loans come with a price, too. You’ll need to pay it back within a certain time frame—plus interest.

    The route you take depends on your company and its goals. Either way, there’s a bit of risk, but the reward can be great.

  3. Begin building your product on the side.

    Your business can’t succeed without something to sell. I’ve seen too many startups trying to sell a product that isn’t yet built. It doesn’t work. You need something, even if it isn’t your final version.

    For me, this was easy. I provide a service (writing), and I have years of experience fine-tuning my trade. But I still thought through exactly what type of writing I would offer and how much it would cost.

    Remember, your product doesn’t have to be in its final form. But, while you’re at your 9 to 5, it helps to begin thinking about how to get your product up and running quickly. You don’t want to spend years building a product before you can secure sales.

    That said, if it will take years before your product is ready, this is an even more compelling reason to seek support from investors or take out a loan.

  4. Promote, promote, promote!

    Don’t be afraid of promoting your idea or skill while you’re at your 9 to 5. Sure, you might risk your manager hearing about your new business venture. If that happens, just position it as a hobby or explain that you’re further developing your professional skills.

    A few ways you can promote your business:

    • Set up a website using Squarespace, Wordpress, or Wix.
    • Post on social media channels, like Facebook, Twitter, Instagram, and LinkedIn.
    • Attend events (think farmers’ markets, conferences, or other community events).

    The truth is, you should be proud of your business venture, not afraid of being criticized. And, if you do get slammed for starting your own gig on the side, then it’s even better for you to go solo—and soon.

  5. Take the leap. There’s never a “perfect” time.

    When it’s all said and done, there’s never a perfect time to start self-employment. There will always be a reason to hold back. Within reason, try to ignore your trepidations. Owning a business isn’t for the faint of heart, and there is risk involved.

    But as a fellow business owner, I want to tell you the truth. I wish I had made the leap earlier. It’s satisfying to develop my own product, choose my customers, and grow my company on my own terms. I’ve also never worked harder. I’m more motivated, energized, and excited when I go to work.

    So if you’re ready, go for it. What’s the worst that can happen? You realize you’re not ready and gain an incredible learning experience. The best case? You start your own gig and never look back.

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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!

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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