Skip to content

Highly Self-Employed

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. Melissa Danielle on January 27, 2014 at 1:34 am

    It took me a long time to acknowledge that I was a HSP. I spent many years cycling in and out of jobs that left me exhausted, drained, and physically sick, thinking that I just needed to find the “right” job and then I wouldn’t feel this way again. Even though it’s been rocky at times, self-employment definitely ended up being the right “job”.

    • Maria on January 27, 2014 at 5:12 am

      Thanks, Melissa for your feedback. I am hearing from more and more HSPs that self employment is for them. It can be an excellent way for us to develop our gifts in a way that suits our needs.


  2. Lu on October 10, 2014 at 3:21 pm

    Excellent post. I’m currently employed and actually enjoy my job but find that the work schedules are very difficult on me as an HSP,so self employment sometimes looks like a viable option for me. Hopefully one day I will gain the courage to try it out!

    • Maria Hill on October 10, 2014 at 3:33 pm

      Hi Lu,

      Thank you for writing. I am glad that you are considering self employment because it can offer you greater control over your life. I know how difficult modern work environments are for HSPs so starting to come up with some ideas is worth considering. I am finding that working in stages helps a lot of HSPs. For example: research, brainstorming etc just to pick a path. The researching how to go about it etc. By going slowly you may actually get there faster and in a happier way.

      I hope this helps,

    • Lu on October 11, 2014 at 4:07 pm

      Excellent advice,thanks Maria.

    • Grace Kerina on January 24, 2015 at 10:33 am

      Hi, Lu and Maria

      It’s so true sometimes that something as simple as being able to determine our own work schedule can be the difference between whether a job is healthy or not. Knowing this and doing something effective about it can be two different things! I love your advice, Maria, to move toward the goal in stages. There’s something grounding about doing it that way, I find. It’s like I can remain fully funcitoning even as change happens, versus trying to do too big a jump at once and getting off kilter.

      Do you know about Kaizen? It’s a Japanese concept of taking mico steps to reach a goal. There’s a super little book about it: One Small Step Can Change Your Life, by Robert Maurer. I wrote a little blurb about it on Highly Sensitive Power a while back about how it healped me deal with earthquake preparations (

      I send you strength and hope, Lu.

  3. Dawn on January 15, 2015 at 4:40 pm

    I know this comment can be a bit off-the topic and also a bit late, but I just want to share my experience in case someone out there can give me good advice… First, this post made ever more sure that I’m also not fit for the normal 40-h week, and I’m glad I can work independently most of the time. Still, there are times when I just get so frustrated because of my “silly brain”. Several times a week I solve problems or encounter them in my work -things that I didn’t expect and I can’t solve right away. I have to think a lot, find information, apply it, be critical, create new, brainstorm… all this for a problem that can be very small in the scale of the whole project I’m working with. It can be that I can’t think about anything else besides that small problem, and I’m trying to see the consequences of the problems way ahead of time, and often over think them before I even have discussed them with anyone else, and it makes me exhausted. As a consequence, I may have found a solution, but for the rest of the day, I’m out of the game. Then I always have the feeling that I should be doing more and not wasting half the day being exhausted. I know that sometimes the active moments are also those that give the biggest bursts of ideas, but I would also like to be able to do more “regular” work, or return to doing normal work after solving problems. Have you got any similar experiences, and what have you done to help yourself with over-excitement about work?

    I also worry about what my colleagues think… For example, I don’t think there is anyone else in my small working community that is as sensitive as I am, and I do worry how much the others judge me for my slightly different working style. It can probably seem to outsiders that I don’t do much, simply because my mental health just doesn’t allow me to work long days and weekends, virtually without holidays, as some of my colleagues seem to be doing. I have accepted that this is the only way for me to work at all, and I know I can achieve things, but I get worried with how other people see me. Do you have ideas on how to over-come being bothered by these thoughts? I’m reluctant to tell my colleagues I’m highly sensitive, as I know some of them would regard it as nonsense and others wouldn’t know what to do with that information, so I’m hoping I can deal with this myself… This all is related to the feeling of “otherness” that I often get when working with mostly “regular” people. It makes me a bit sad, since I love my job and it’s the one place where I wouldn’t like to have that feeling.
    Thanks for anyone for reading this long and rambling post:-)

    • Maria Hill on January 15, 2015 at 5:36 pm

      Hi Dawn,

      I think the first issue you have is that you are framing your differentness as a problem which it isn’t really. It is perfectly OK for you to work the hours that work for you and have a different working style. If any one makes a remark, you can frame your different ways of doing things as how you are most productive. Productivity is something they will relate to and if frequent breaks or different work hours (pacing) help you be more productive, what is the harm?

      In relation to your first issue, I am wondering what you mean by being “out of the game”? Does it mean that you are not getting your work done, because that might be a cause for concern. If you are focusing on things that are not material to the work then you might receive some negative feedback. If you are focusing on problems that make a difference how can that be a problem? Different people have different roles, as long as you re fulfilling yours I do not see the harm.

      I hope this helps,

    • Dawn on January 16, 2015 at 3:34 pm

      Thank you so much for responding Maria, and for reminding me that I do not need to be like everyone else (I know that, but still forget…). It is true I simply can’t be productive if I work too much. Second, it does happen that after I get tired from being overwhelmed by some little thing, I do not get any more work done that day, or it is very difficult. I worry that I will end up being behind of my schedules because of this. So in this regard, I would like to control how strongly I feel about the problems I face, so they wouldn’t wear me out.
      I believe this all could be easier if there was more “peer-support” from sensitive people available, do you know if there is a forum or something for us to talk about work life-related topics?

    • Grace Kerina on January 24, 2015 at 10:48 am

      Hi, Dawn

      Oof. That can really be tough, being the odd person for some reason in a group like that. Maria makes some worthwhile points about zeroing in on the work itself. I wonder if it’s an issue of being able to prioritize your work so you can consciously let some problem-solution sets go, even if they would be interesting to solve, so you can focus more productively on the outcomes you’ve been hired to attend to. This is an issue I often come up against, because there’s just SO MUCH I see that would be POSSIBLE to focus on and to improve. Oi vey. It helps me to keep a focus on the end goal in order to decide in the moment what activities to spend my time on.

      I think you’re on to something with your yearning for a community of people who are more like you than your coworkers as regards being highly sensing (I find it easier to introduce people to our trait using the term highly sensing, because it doesn’t trigger their assumtion that the trait is about that other sense of the word sensitive – taking offense easily – and the word sensing is a good lead-in to telling them about how it’s a trail that’s physical in that it’s about the nervous system.

      As for HSP community, I’ll bet Maria has some ideas. Peter Messerschmit oversees the Pacific Northwest HSP Network (online) if you’re in that area. I’ve dealt with this issue by collecing HSP and building those relationships to stick, even if one of us moves, because they’re so valuable.

      Something you might consider is choosing to “come out” to someone at work. Perhaps there’s someone who’s most likely to be supportive if they know about you being an HSP. You could take them out for tea on a break and share this important thing about yourself and ask for their support by simply knowing this about you. Or maybe you can think of another way to not feel so alone at work around this issue. By now, after many years of becoming comfortable with the trait, I tend to tell people about it, especially if I suspect someone is an HSP themselves. I’ve made new friends that way.

      Long answer. Thank you for reading. I wish you ease at work + friendship.

Scroll To Top