How to Be Self-Employed, by Someone Who's Been Self-Employed Almost Two Decades | Fairygodboss
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Work For Yourself
I've Been Self-Employed Almost Two Decades — Here's How I Make It Work
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Jennifer Mayer,

Why do you want to be self-employed?

Being self-employed is great — you get to set your own hours, you are your own boss and you get to make the rules… which also means you have to set your own hours, you are the boss and you have to make the rules!

Over the past 16 years I’ve been self-employed and have operated four different businesses mostly from my home. When you run your own operation, there are so many tasks that must be achieved. Everything from making sure there’s income coming in, that the business is well prepared for tax time, that income tax is paid and that all deductions are ready for the accountant are just some of the tasks required when operating a home-based business as a sole proprietor.

Aside from the business aspects, which can include deciding your self-employed health insurance, self-employment income, how you manage your expenses and more, you need more than a first-line supervisor to take care of your business — and you. I’ve learned by trial and error what’s worked to keep operations afloat daily. 

How do I become successfully self-employed?

Here are the key daily habits I recommend:

1. Set a schedule.

When you’re self-employed, you can almost work anytime — which is hard to manage. Setting a schedule for “office hours” and having predictable times when clients can reach you will prevent burnout. If you know that there are certain times you need off but have clients who want to work with your business during those times, consider hiring an independent contractor or additional workers for additional support.

2. Create systems.

As someone who is self-employed, you need to wear a lot of hats! Without systems in place, things can quickly become confusing, especially if you’re keeping track of everything in your head. Some simple systems that are helpful to put into place are: having a process for inquiries, having processes in place for starting a new project, and creating procedures for the end of a client experience that includes asking for feedback and testimonials. Quickbook Online can help you stay organized, as can custom budget sheets and trackers.

3. Know when to stop working.

It’s so easy to just “do one more email,” or work all day and all night to achieve your dreams. But having a hard stop to your workday will prevent burnout. At times, you will have deadlines where you’ll need to put in extra hours, but on a regular basis, having time off is essential. Remember that you are your own employer, and any good employer would want their employees to take care of themselves!

4. Go with the flow.

Being self-employed is often feast or famine; you either have too much work to handle or not enough. Perhaps you consistently alternate between a salary deferral and catch-up contributions, or perhaps you feel that your work is more part-time work than not. Using the downtime to work “on” your business, rather than “in” your business is key. Just doing a few things to move the needle forward can help spur new business opportunities.

5. Schedule recurring admin work.

Yes, there are tasks that will always need to get done no matter what. These include monthly and quarterly financial reports, keeping track of expenses, completing online courses or staying current on your certification or license if you have one. It also includes larger tasks that impact the bottom line, including invoicing a business expense, tracking self-employment earnings, social media management and more.

6. Delegate.

Sometimes, as a sole proprietor, there’s just too much on our plates. Being a self-employed person means that you need to be able to occasionally delegate tasks so you can better your client’s experience. Though there is a business cost, the self-employment assistance is worth it. Know what you’re good at and what you're essential for, then delegate out the rest.

7. Take care of yourself.

When your business is just you, your business needs a healthy you. Maintaining your health through proper nutrition, exercise and adequate sleep will have an irreplaceable ROI for your business. Self-employment requires a great deal of self-care, so don't hesitate to spend net earnings on something that benefits your mental health.

8. Socialize.

There’s more to life than just work, though often those of us who are self-employed are super passionate about the work we do. Having a hobby or a group of friends separate from work can give you a much-needed break to refresh and refuel. You won't have a traditional employer-employee relationship to rely on, so building a separate group of confidants is key.

9. Create a support network of like-minded allies.

In business, it is so important to have a supportive network of colleagues and associates who support one another. There are many challenges that come with being self-employed, and sometimes our spouse, significant other, family members and friends just don’t understand. Having self-employed allies you can reach out to is essential.

Being self-employed and home-based employment doesn't mean that you have to make your business your number one priority. Remember to take care of yourself and to focus on work-life balance, and you'll go far.

What do I need to be self-employed?

  • Discipline and drive
  • Medical insurance through the marketplace or from a spouse 
  • The ability to set aside roughly 30% of what you earn for self-employment taxes and accounting

What are the highest paying self-employed jobs?

The top hourly rates for self-employed jobs, according to Upwork, quoted by MONEY online:

  1. Network analysis ($200)
  2. Computer vision ($145)
  3. Chef.io ($140)
  4. Neural networks ($140)
  5. Firmware engineering ($130)
  6. Hardware prototyping ($130)
  7. Cloud computing ($125)
  8. Intellectual property law ($120)
  9. Trade law ($115)
  10. Privacy law ($115)
  11. Spatial analysis ($110)
  12. Apple Watch ($110)
  13. NetSuite development ($110)
  14. Acquisition strategy ($110)
  15. Algorithm development ($100)
  16. Software debugging ($100)
  17. Digital signal processing ($100)
  18. Ad lyrics writing ($100)
  19. Natural language processing ($100)
  20. Data processing ($100)


Jennifer Mayer supports parents through pregnancy, birth, new parenthood and the transition back to work. Shes the founder of Baby Caravan, a birth & postpartum doula agency and Baby Caravan at Work, a corporate consulting practice based in New York City. Jennifer lives in Brooklyn with her husband and son.


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