For much of my working life (and I’m in my 50s, so it’s been a while), I struggled with the demands of the “normal” 40-hour work week.

Working the way our society seemed to insist I work in order make a living made me feel like I was dying. I needed more peace, more depth, more meaning, more self-direction, and more time off than any of the jobs I found seemed to offer.

I would do my best, but over and over again, after a few weeks or months, I’d become so sick and tired that the only way I saw to choose life over death was to quit the job. I’d rest up a while, then be back at square one, frustrated by the outlook.

The Path To Becoming Self-Employed

As a way to avoid that unhealthy pattern, I began flirting with becoming self-employed, at first trying it out in addition to part-time jobs and in spite of not knowing how to do it. Whenever I achieved some success at being self-employed, even if only temporarily, I was much happier. So I took workshops and read books about self-employment and I experimented.

Over the years, I tried different self-employment activities, searching for ones that would succeed for me and my particular needs and HSP traits, ones that would give me enough money to live on and feel like making a living (vs. a dying). I tried consulting about different things. I tried making and selling art. I tried collaborations and self-employment systems others had pioneered.

A major shift occurred when I changed my perspective from asking myself, What can I do that will make me money as a self-employed person? to asking, What am I already good at that helps the people in my life? I started paying attention to what came naturally and easily. I started noticing what others valued about me and valuing myself more as who I was rather than who I should be.

When one of my housemates timidly asked me for a beginner’s lesson on the computer because “You know how to use a computer, I don’t, and I know you’ll be patient with me,” I paid attention. When friends called me weird for staying up late having fun using a bookkeeping program, I paid attention. When I eventually had a waiting list for my bookkeeping services, even though I wasn’t a trained or even a very good bookkeeper, I paid attention.

Being Nice Pays

I took a step up in self-employment when I figured out that people will gladly pay me to be nice to them as they learn. People will pay me to witness their learning process with kindness rather than judging them for their stumbles.

I took another step up when, after observing (and living with) my income struggles for years, my husband said to me one day, “You know, it’s kind of obvious that you need to focus on raising the amount of money you get per hour.”

Raising my rates became a reality when I paired my HSP-strengthened quality of attentive empathy with something I’m passionate about: writing. Gradually, I figured out ways of specializing in helping people write and became good enough at it to earn at a rate that supports me without requiring more of my time than I can healthily give. It feels infinitely fun to continue finding more ways to help people write as I also help myself thrive in my work.

Why Being Self-Employed Works For HSPs

When I wrote a blog called Highly Sensitive Power for a couple of years, I reached out to other HSPs and learned a lot about their struggles and their solutions. There are many self-employed HSPs who are happy doing what they do best: being an HSP and working with passion. They’re thriving within the constellation of being their own boss, being free to change and grow, and focusing on what they enjoy doing.

For HSPs like me and many others I know, the Internet makes it possible to work from home on my own timeline while still providing my clients and readers with the services they need. The Internet, as a tool, tipped the scale for me, making my working life increasingly joyful and profitable. So much is possible online – connections, communities, and resources that tap into the world’s population and wisdom.

If you’re struggling with income issues and your health is suffering because of it, consider the option of becoming self-employed. You deserve a working life you love. And your potential customers deserve access to your special wisdom.

Being Self-Emplyed Can Be Profitable

Here are some questions to help you clarify ways of moving toward healthy self-employment:

  • What do people ask you to help them with?
  • What are you passionate about (particularly in a way that’s ongoing versus fleeting)?
  • In what ways does or can the kind of help you’re asked for intersect with what you’re passionate about?
  • How can you explore and develop those intersections as self-employment possibilities, even if only in small or experimental ways for now?
  • Who do you know who’s both an HSP and self-employed? Would you be willing to ask them to share their wisdom and/or tell you their story about becoming a self-employed HSP?
  • What would your ideal work be? What specific elements of that work can you include in your explorations about self-employment?
  • If you’re interested in being self-employed but have fears, what are they?
  • What are some options for getting help with working through those fears in meaningful ways?

There’s a wealth of wonderful, useful information to be found regarding self-employment, but because there’s so much, it can be overwhelming to begin. To offer you a supportive nudge and a way in, I recommend the two resources listed below. They’ve helped me the most on my journey of creating healthy, ever-improving self-employment that really works for highly sensitive me:

  • Barbara Winter’s book Making a Living Without a Job: Winning Ways for Creating Work That You Love (there’s now a revised edition), and
  • Darren Rowse’s Problogger website and e-books, which are packed with inspiration and practical tools for creating and growing an Internet-based business.

Good luck, and make sure to spread the word within the HSP community if you become your own boss. We’re rooting for you.


About gkerina

As a freelance writer, editor, and teacher, Grace Kerina’s mission is to eliminate writer’s block from the planet. She pays close attention to what makes people stop writing, creating, or living true and comes up with ways to help, some of which are on the wacky side but still weirdly work. Her e-courses, services, and publications help writers tap inspiration so they can share their wisdom and make a difference. Connect with Grace at her website.


  1. Grace Kerina on February 10, 2020 at 6:15 pm

    Thank you, Mina!

    Hey, I hear you about self-questioning and building a business doing what you love. Here’s what I believe: If we are called toward offering something as a service, there will be clients. There WILL be clients. The task is to find them and connect with them, and to build your chops in your calling-field. How would it feel to really lean into the work that’s calling to you?

    It takes courage to explore in the way you’re exploring. I wish you oodles of success!