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HSP Topics: Work and the Highly Sensitive Person-- Self Employment

Peter has written extensively about high sensitivity since 1997, when he first learned he was an HSP.


This article is part of an ongoing series about the ups, downs, joys and sorrows of life as a Highly Sensitive Person (or HSP). It is also one of several articles focusing on HSPs and work-- an often difficult area of life when you're highly sensitive. The first article explains some of the challenges and difficulties HSPs face at work.

If you are not entirely familiar with the HSP trait, or feel unsure whether or not you're even an HSP, I recommend reading my initial article on the subject The Highly Sensitive Person: An Introduction which also contains an index to many of my HSP-related articles. You may also wish to take Dr. Elaine Aron's free self-test for sensitivity, which can be found on her web site.


If you're an HSP considering self-employment, be sure not to miss Barrie Jaeger's book about HSPs and Work!

Self-employment as the path to a True Work Calling for HSPs

In her book "Making Work Work for the Highly Sensitive Person," Dr. Barrie Jaeger states that self-employment can be one of the best-- and often most certain-- ways for an HSP to work with their true calling. As a self-employed HSP, myself-- albeit with a background in corporate jobs-- I agree 100% with that assessment.

The beauty of self-employment is that not only do you have the opportunity to create the job you perhaps couldn't find in the general job market, but you also have a lot more control over your work environment-- something that can be especially important for HSPs.

Of course, before you can even consider self-employment, you need to be fairly clear about what you want to accomplish, especially making sure that you identify your "calling" in a work context. Identifying your calling and then determining how to turn it into a commercial enterprise can be both challenging and time consuming! Short of pursuing your calling, you at the very least need to have a marketable skill (or product) you feel passionate about, and that won't frustrate you after a short while.

Although it may sound obvious, I have often been surprised by the number of people who become self-employed for no better reason than "it sounded good and I was tired of working for someone else." Simply "picking something" will more likely be the road to disappointment than the road to success.

This article will focus primarily on the type of self-employment an HSP can start from home, as an individual, working just for themselves. Often such a person is referred to as a "sole proprietor" or "solopreneur." Because the field of self-employment covers a lot of ground, this article should not be regarded as comprehensive or exhaustive on the topic-- this is merely intended as a primer on some of the most important things to consider.


A few words about HSPs, Self-employment and "Risk Taking"

When it is first comes up in conversation, many HSPs actually shy away from the thought of being self-employed. The most common argument is that starting your own business is "too risky." The next most common argument is that being self-employed is "too complicated" or "too difficult."

So let's start by looking at risk and examine "perceived risks" vs. "actual risks."

Many of us may have read articles in newspapers and magazines, citing statistics like "80% of small businesses fail within their first three years." Whereas this may be true, it's important to know that the vast majority of these involve entrepreneurs who go out and secure bank loans, then open a "physical location" of some kind with buildings and/or equipment, and then hire a bunch of employees. Very few of these failed businesses are the ones started by an individual-- or couple/family-- out of their home.

Much of the risk of getting in business for yourself can be assessed by examining and answering two important questions before you get started:

A Fairly Recent Book, About Finding Your Calling

One, do you have the right personality to be working for yourself? People who depend heavily on others for motivation, and to tell them "what to do," and who have trouble making decisions generally do not make good "solopreneurs." Also, take a look at your organizational skills. Being self-employed doesn't require that you're always well organized... but it certainly makes your life a lot easier! Also consider whether you're disciplined. Do you tend to do stuff "whenever," or according to an inner sense of "keeping things orderly?"

Next, take a long hard look at your idea for what you want to do. Sometimes there are great ideas... but they may not make practical sense. You may be an extraordinary landscape gardener, but if you live in a tiny town far removed from the nearest population center... there may not be enough business for you to make a living. Similarly, you may make the best cupcakes on the planet-- but if there are already three great bakeries in your town, you might pause and take a long hard look at whether or not you can sell enough cupcakes to pay your rent and put food on the table.


Self-employment is NOT a get-rich-quick plan!

We sometimes hear or read about people who became "overnight successes" with a business idea. Indeed, such things do happen.

However, these successes happen very rarely. Most solopreneurs face a "burn-in period" that lasts from months to years, before they make a significant income. Thus, self-employment is seldom the best place to start if you're facing a life situation in which you "really need money, NOW." Also keep in mind that these "instantly successful" people may have spent years in the planning stages, before they launched that "as seen on TV" product now selling by the millions. We just don't know what happened before the success that becomes "public."

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A more practical consideration is that 99% of business ideas require us to put at least some money into our new venture up front... and then there's going to be that "lag time" before money actually starts to flow in, simply because it takes your potential customers/clients a while to figure out that someone is now making the world's greatest cupcakes, right here in their back yard.

This may not be what you want to hear, but if immediate financial need is the primary motivator driving you towards self-employment, you are probably much better off looking for a temporary job until you have saved enough to get your business up and running without having to worry about every single penny you are spending. There are exceptions, of course...


Before you start, have a plan!

Planning and goal-setting are vital parts of becoming self-employed-- their importance cannot be overstated. Large numbers of people start-- and fail at-- their own businesses because they "just started," without really planning or thinking through what they were trying to do. It wasn't that their ideas were bad, it was the poorly planned execution of the ideas that caused the problems.

Over the years, I have met many small business people who may have had great ideas-- but their ventures failed because they had very little sense of where they were going, nor what was needed to get there. For a highly sensitive person, this can be particularly important.


The majority of HSPs are "creative" types who often don't really enjoy the "business" and "financial planning" side of being self-employed. But it's dangerous to ignore "the numbers," and you can greatly increase the chances of successfully reaching your dreams by taking time to plan ahead.

A good business plan doesn't have to be complicated, it just has to be specific. If you have access to a piece of land and want to grow organic herbs to sell to restaurants and natural markets it's not enough to say "By next year I want to be making a living selling herbs." What does that mean, to you? What is "a living," in money? What will you sell each bunch of herbs for? What will your seeds, seedlings and other supplies cost? How many bunches of herbs will you actually need to be selling every week or month, in order to be making your definition of "a living?" It's very important to spend some time visualizing and walking through every step between "here" and where you want to end up.

Of course, money is an important part of almost every business plan. If you don't have any savings, you may discover that you need to stay with your current job for a couple of years and live a really spartan lifestyle so you can set aside $200 a month for start-up costs. You'll need to plan how to reorganize your life to make that possible.

A cautionary note about planning: Almost every person with an idea believes they are going to get more successful, more quickly, at lower cost... than they really are. The first business plan I wrote not only considered my estimate of how business would turn out, but also an estimate of a "30% below expectations" estimate. If the plan still works, you may have a winner!


Controlling Risk: Taking the Gradual Approach

The vast majority of sole proprietorship businesses are actually not started by people who have a paying (but difficult or boring) job one day, and then jump 100% to being dependent on their own work, the next.

I personally spent several years "preparing" to become a self-employed writer, coming up with a number of different ideas and angles I wanted to explore. Then I spent couple more years being employed full-time, while I took more and more "on the side" writing jobs-- some technical writing, some writing for advertising. Eventually, I was getting enough contract work that I could cut back my hours at my regular job while still building my home business, until one day I was able to be 100% independent.

Since HSPs tend to be "risk averse," I highly recommend taking such a "test the waters" approach to self-employment. Spend some time mapping out where you want your business to eventually be, and create a "timeline" for getting there. As stated previously many HSPs are "intuitives" who really don't like "planning," starting a business is one of the few places where you really don't have a lot of room to "fly by the seat of your pants." You don't have to plan extensively, but without at least the "bare bones" of a plan, your risk of failure and disappointment increases many fold.

An additional benefit of the gradual approach-- which tends to appeal to the highly sensitive-- is that it allows you to take more of a "soft sell" approach. Since you're not initially wholly dependent on your self-employment income, you don't have as much pressure to "pound the pavement and be in people's faces" to market yourself and your service/product.


Self-employment doesn't HAVE to be "complicated!"

It's a common misconception that self-employment-- that is, starting a small business or simply working for yourself-- is "extremely complicated."

Whereas it sometimes can be complicated, most of the time it is not... and this fear should not keep you from starting a business on your own.

What can make self-employment "complicated" is opening a "facility" of some type-- a restaurant, a retail shop, a manufacturing venture. Such ventures are little outside the scope of this article, and are best undertaken by people with business and management experience. If that is your inclination, there are already a number of good books on the market, even if none of them are written specifically with HSPs in mind.

The vast majority of "solopreneur" businesses are started from a desk at home, or from a small space in a garage. One of my previous businesses had its "home" in a 10x10 foot space at one of those "self storage" rental places. My "office expense" was less than $80 a month. I had a product to sell and kept boxes, packing material and inventory at the storage space and did my paperwork and billing from my computer desk at home.

If you are selling a service you provide, or a product you already know how to make, odds are your biggest investment will be time. And a large portion of that time is likely to be spent on marketing-- basically letting people know that you have something to offer. And that's another important point for HSPs considering self-employment: If you don't have the stomach for extensive self-promotion, you may want to think twice about getting in business for yourself.


Practical considerations: A few Basic things you'll need

So, if starting self-employment isn't "difficult," what DO you need? Keeping in mind that laws are different from place to place, there are certain things that are required in most places.

If you are going to do business as anything other than "yourself" (i.e. use a name like "Sunny Acres Organic Herbs") you will almost certainly need to apply for a business license, which will include filing an "assumed name statement" or DBA ("doing business as") so that you can legally use a business name. Where to file your application varies from place to place. A good place to ask for help (aside from Internet research) is your local Chamber of Commerce.

In most places, selling a product or service will require you to collect sales tax or VAT or PST/GST, so you'll have to apply for a tax permit. Again, you'll need to check your local, state/provincial/county and federal laws for exactly what you need. Tax permits may have a complicated application process, but seldom cost much money for an individual starting a business.

Once you have your business license and tax permit, you can open a business bank account. Some will advise that a business bank account is "not necessary," and that can be true. However, it's just good practice! And it's much easier to track your business expenses and receipts when they are not mixed together with your grocery receipts.

Get yourself a dedicated notebook to write in, where you can "log" everything you do with your business-- from new ideas, to reminders, to journaling and more. This will also keep your tax department happy if you lose money your first year and take a tax deduction-- you'll have proof that you were "seriously engaged" in running a business.

To keep organized, get yourself a box and some manila folders for receipts, bills, client contact information and so forth. As every business is different, I can't offer you the specifics here, just a general overview. What is important is that it's much easier to keep good records from the start, rather than come back later and try to get organized "retrospectively."


Going forward: Why some succeed and some fail

Self-employment or solopreneurship is not for everyone. Certain things are required, if you want to succeed.

Perhaps most important is discipline. Even though it may feel wonderfully freeing to not be commuting, and working in your sweats-- remember that this is your job; your livelihood. And it must be treated as such. If you are working at home, there are dozens of tempting distractions all around you, all the time. The lawn may need mowing; a friend may want to have a two hour lunch with you; checking what people are saying on Facebook beckons; you really meant to get the bathroom cleaned.

Whereas you certainly have more flexibility when you're self-employed, your business will never succeed if you find yourself looking at 2:30 in the afternoon and all you've done is answer a few emails and distracted yourself with Facebook. Maybe that seems "obvious," but thousands of home business owners fail (or quit) every year because they lacked the discipline to "manage their business."

As I pointed out previously, before you go any further, take a long hard look at your personal work patterns and ask yourself-- and make an honest assessment-- as to whether you have the discipline to focus on work. There's nothing wrong with wanting to work from early afternoon to two a.m. every day... as long as you work.

Second, make sure your motivations for starting the business are clear. If your first answer is "for the money," odds are-- especially as an HSP-- that you'll fail.


Because you'll end up in a drudgery situation where you care as little for what you're doing as you did about the soul-sucking corporate job you left. As an HSP, make doubly sure that you are getting involved in something because it genuinely feels like your calling-- or something reasonably close to it. Of course you want to make money-- a good living-- but that should be the result of pursuing your calling, not your primary motivation.

If you're passionate about what you're doing, odds are that others will sense your enthusiasm and support you. Enthusiasm is infectious!


Even "Callings" have their "drudgery moments"

To create the opportunity to pursue our authentic callings can be a wonderful experience!

As a long time self-employed person-- and a consultant to hundreds of "solepreneurs" over the years-- I would like to bring up one final caveat about self-employment:

No matter how amazing your new self-employed work may be... it will have its "drudgery moments." Where those will actually arise is all but impossible to predict. For many creative type HSPs it's bookkeeping and taxes. For others, it might be "marketing yourself." If you're selling a product you're creating, it may be packing and shipping. The important thing to know-- and keep firmly in mind-- is that there is no form of employment that is just 100% wonderful, 100% of the time.

Ideally, you'll eventually succeed to a point where you can afford to hire someone to deal with the parts of running a business that lowers your enthusiasm for what you're doing. However, unless your business takes off incredibly quickly, odds are it'll be several years (maybe even 5-6) before you can financially justify "hiring out" the drudgery aspects of the business.


Patchwork Economics: Self-employment income from multiple sources

One of the common misconceptions about self-employment is that your entire living has to come from just one source. Whereas this line of thinking works for some, it also tends to set limitations on people who subsequently fall into the trap of thinking "Nice idea, but I can't make a living from just THAT!" when looking at some of their best ideas as potential money making sources.

True, maybe you can't. But what if you had three or four "complementary" businesses centered around a "loosely common thread," each of which were very part time? Maybe you can't make a living from just one of them-- but adding all four together might afford you a very comfortable life.

Whereas the majority of the self-employed work at just one business, don't overlook the possibility of creating a system of "patchwork economics," in which your living is derived from several sources. In addition, you may find that there is less competition in areas that don't appear capable of generating a "full time" income stream for someone.

I personally pursue such a strategy, and have been for many years. I currently have five distinct income streams from self-employment-- non of which (by themselves) could earn me a living. A couple of them could probably be turned into viable "single businesses" if I did nothing but work at them, all the time. But I don't really want to-- and the diversity keeps me interested in what I am doing. And if I get "bored" with one area of work, I can go work on another... which is also appealing to many HSPs.

A very useful book!

Famous Last Words: Monetary vs. "Psychic" Income

Ultimately, the purpose of working is to make money; to earn a living. Unless we happen to be "trust fund babies" who can work simply for fun, we work because we have bills to pay; food to buy.

Not all the gains you get from working for yourself-- especially if you have the good fortune to have found your true calling-- are monetary. There are benefits you get from a home business that can't be measured in dollars and cents or pounds and pence.

For example, you can't place a monetary value on the reduction in your stress level, when you move from a semi-hostile office environment to your desk at home. You also can't place a direct monetary value on not having a 45-minute (or longer) commute to work, each way.

You also can't place a monetary value on "psychic income." What is psychic income? Well, it could be the way we feel when a client tells us that our product/service is the best they've ever had-- AND we get the full credit for our efforts, rather than a "footnote" in a manager's report. Psychic income is what we get when we wake up in the morning and "can't wait" to get started on another workday... because we feel excited about what we're doing, and like our contribution matters.

Psychic income is also why many self-employed are willing to take considerable pay cuts to work for themselves, and are willing to make lifestyle changes to keep working for themselves.

Many HSPs choose to work for themselves-- and in many ways, going out on our own is ideally suited to our sensitive natures. Maybe it's the perfect solution for you, too!

Please Share!

If you enjoyed this article and/or found it useful, please consider sharing it with others! You can use these nifty "social sharing" buttons, out at left. Thank you!

Talk Back! Are you an HSP looking for your calling? Or have you already found it? Have you considered self-employment? Are you currently self-employed?

Sharilee Swaity from Canada on January 22, 2016:

Hi Peter,

I just wanted to leave another comment on this article, too. I love your summary of good and bad points about self-employment, especially for the HSP, and agree with the points you made.

The risk-taking part of self-employment has always freaked me out (and I have tried it twice) and sent me scurrying back to the saftey net of teaching. But this article has helped me understand better what I need to do ... to have a more concrete plan, and to allow myself to do more than one thing.

I find it's hard to explain my plans to non-hsp's because they think you are unrealistic. So hard to keep those dreams safe, from other's cynicism!

Connie, Stord, Norway on March 01, 2014:


I hope this site is still open....:-)

Thank you so much for sharing !

I am an independent entrepenour, but i do not dare to tell anyone....

It is so ironic and so true. I want to and i do ( a few times) give speeches on Mental Health Care.

But as soon as I have held a Speech i run back home and stay there for a loong time. I enjoy being on stage as I do believe in my perfomance and the idea for my speeches, - ironically I just hate having to promote myself. Som kind of massive unsequrity just overtakes me afterwards.

So now i have to learn how to work With ME - cause that really is the greatest Challenge.

I have spent many years in different jobbs, and never quite found my spot. I read all you wrote above- and I see there really is just one way for me to work and it is With myself and for myself

Catherine Elise on December 10, 2013:

Thx for your articles! I am an HSP....all that you write is so dead-on for me. I appreciate the support! I am once again exploring what's next for me for work. Exploring the concept of the "calling".... I like the idea of having several going (like you) at once (and linked). Makes sense to me.

I really need some income now. I left my last job-it was way too overstimulating to be able to make enough for rent etc. (could only work three days a week-the rest of the time spent recovering)--prob left too soon, but the management started breathing down my neck--and you know how us HSPs feel about that!!! Since.. I have had a lot of self-employment little jobs that have been time limited. I want something more sustainable. Like you said...I don't need much materially. I am great with people-- Intuitive and insightful. I like to write...I just got into making videos and LOVE that....really fun. I like being in front of the camera and talking!

I am going to try your exercises....5 things I loved as a kid. I remember loving hosting and recording variety radio shows with my sister and friends.

Thank you agn for your writing.

Peter Messerschmidt (author) from Port Townsend on December 21, 2012:

Thanks for commenting!

Erik Thor-- self-employment can be a pretty good gig, but I think you hit on a key point: when we feel inspired, we do good work, and typically enjoy it, too.

Mizjo, thanks! Getting a stable online income takes time-- just like everything else. A lot of people end up disillusioned because they think the Internet is "fast," so money online should also be fast. However, with diligence and ingenuity, it's certainly possible to build online income.

Erik Thor on December 13, 2012:

Great work! I'm planning on going down that road myself one day. But I've had good success at work too, because I'm quite diligent with what I do, if I'm inspired.

mizjo from New York City, NY on December 12, 2012:

Wow, great reading, denmarkguy. You've touched on all the important start-up tips for self-employment. I started on them not long before I retired, hoping to make an online income. So far, the online part is about a year old, and the income is maybe $15 year!

I'm reading all I can to do better, and thank God I don't rely on that for food and shelter. It is my calling, though, something I enjoy doing, so discovering the internet is a blessing for me. If I can make some decent money would be more than the icing on the cake.

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