Self Employment: The Independent Work Option


I’m a 52 year old male living in the western United States. Having worked for other companies and people for a number of years, my experiences led me to believe that self employment would be a better vocational option.

For the last 13 years I’ve been self employed, working closely in the property development sector with a contractor friend , Dave, doing construction related tasks like painting, dry wall repair etc. More importantly, I’ve been acquiring and renovating rental properties that I rent out and manage.

I don’t have a diagnosis of Asperger, but my difficulties with social interactions, eye contact, obsessional interests, literal interpretation of speech are consistent with AS. I also seem to have a major case of Attention Deficit Disorder or ADD, which makes focusing, and following through on tasks, very hard unless the activity happens to coincide with one of my strong “interests”. Here is a brief account of a late bloomer and how opting to be self-employed has been beneficial for me.

Exact details in this case study have been changed for confidentiality reasons. The views expressed are personal, for illustrative purposes only and should not be related, or automatically applied to, other situations or scenarios.

Case Study

I graduated from college in 1979 with a major in education, with teaching juniors in health and mathematics. After graduation, I felt unprepared to teach, or find a white collar job appropriate to my educational level. I have very poor clerical skills and hate dressing up in a suit and tie; if I do, I feel like I’m suffocating. Initially I worked at various blue collar jobs, driving trucks, doing maintenance work etc.

After getting married at age 30 my wife and I bought an older house in a downtown area. I greatly enjoyed working on it and started to dream of buying properties and fixing them up. I’ve always enjoyed working hard, but I wanted to work by myself in an environment that allowed me maximum control over my work conditions and surrounding. I’m very sensitive to noise and dust so I wanted to be able to wear a dust mask and ear plugs when needed. In addition, I get bored easily and like to listen to current events on National Public Radio while I work. Also, I like to work to high standards that sometimes cause me to work slowly and I have an ethical problem with wasting time on someone else’s dollar, I can get very stressed worrying about time dead lines. I think the sensory sensitivity, deadline stress, and perfectionism are AS traits and the boredom is possibly related to ADD. At this time, I started to follow the local real estate market, collecting information on sales prices, location etc. I wanted to own rental properties, but I was fearful of really making the financial and emotional commitment to buy.

For the next 9 years I continued to work at various jobs; I even taught junior high school mathematics for part of a year. I started teaching the same week my father died so I was stressed to start with. I had done some tutoring and really enjoyed it, so I thought that teaching might be a good outlet for my desire to help others.

It was probably the worst set of circumstances I’ve ever encountered. After interviewing, three schools wanted to hire me, but rules dictated that I had to go to the first school on the list. It was a fairly rough school and the emphasis was on maintaining control, with learning a distant second.

I really enjoyed the students, especially one class of “odd ducks”, but I found my interactions with the other teachers mostly depressing. The pay was low so by the time they deducted health insurance expenses I just couldn’t survive. This experience strengthened my desire to work for myself, but I was held back by my lack of initiative, poor organizational skills and fear of the unknown – all traits associated with Asperger.

Then, in 1995, the parents of some our friends were retiring and offered to sell us one of their investment properties. They wanted to sell it on a 25 year contract to provide a revenue stream to supplement their retirement incomes. I was anxious about taking on the responsibility of a rental property, but my wife insisted that we buy it. I think she was tired of listening to me talk about owning property and not following through on buying any. She argued that we could handle taking care of the property and addressed my fears one by one. She really convinced me we could handle anything that came up. I think that part of the reason I agreed was that I felt guilty for not being able to support her more successfully. We bought it for a very good price, and suddenly I was a landlord!

After closing, I fixed up the property and raised the rents to match the local market. Three years later we bought a quadplex, two years after that we bought another quadplex. We have also bought a house which we rent out, and we own a building lot in a small, rural area that we hope to retire to. We leveraged (borrowed against) the properties fairly heavily, but we chose them carefully, and they all had good cash flows.

They are also in good locations with nice floor plans, and no multi-story buildings, which I don’t think make for good rentals. Everything I learned about being a landlord was from direct experience. I tried reading books on real estate investing, but none of their advice worked for me. I think that books didn’t work because I was working “against type”.

My motivation was to find distressed properties and make them whole, and usable, and provide housing for people. The writers of books on real estate are appealing to people’s desire to make easy money, and I wanted to make money, but not at the expense of my tenants, or the people I bought from. Maybe It related to the inherent honesty related to my [AS] condition. I wanted to progressively build a solid foundation of serving my tenants, improving my properties and gradually paying down our loans, not the sort of things that make a good book on how to get rich quick. In addition, I learn best by jumping in and doing things, which is contrary to my natural cautious nature. Sometimes I need that little nudge and my wife, who is fearless, provided that push.

I’ve done most of the renovation work on the properties myself and hire out jobs requiring specialized skills, like furnace repair, or major electrical work. All of the money we generate goes back into the properties either through fixing them up or by accelerating the mortgage pay downs. It was especially important to pay down the money owed, since debt represents the control others have over me, something that I’m not very comfortable with.

I do all of the regular maintenance, and try to attract good tenants by keeping the properties in excellent shape. I find it very important to provide clean, safe and well maintained homes for my tenants. Many of them have had bad experiences with landlords and I try not to take advantage of their trust.

After some bad experiences with rental agencies, I now interview the prospective tenants myself and have had good luck. The agencies provided good tenants, but they were often not good “fits” for my units. It is hard to describe, but with my best tenants something just clicks and I know they will work out. They seem to be genuinely excited about the properties and having me as a landlord. This just didn’t happen when renting through agencies. I think my AS has made me hypersensitive to the intentions of others, and this is what I’m sensing when I talk to prospective tenants.

Because our rentals were highly leveraged when we first bought them, I reduced this element of risk by keeping expenses low, and very actively managing the properties. I realized that over time almost all real estate can be profitable and this has turned out to be true in our case. My wife works as a professional in the non-profit area. Her steady income allowed me to have health insurance and enabled the properties to be seen as long term investments. I think that the properties represent quite a bit to me. I’m very competitive and working at low wage jobs has always been a bit of a come down for me, the properties represent a form of legitimacy and allow me to pay back my wife for all of the work she has done for us over the years. I’ve worried about money in the past, but her working has kept my concerns inside my limited tolerance zone.

Working with Dave, has given me a job that is very flexible and provides a source of support for my renovation projects. Dave and I share a common sense of integrity, and our intention is always to worry about the job first and money second.

He is very good at all the things I’m bad at. He does all of the billing and deals with the clients almost exclusively. He looks at the overall job and has me do certain segments of the project. I do small jobs for people on my own, but I hate the interaction with people and I’m not good at keeping records and billing. He works around my numerous foibles and is very understanding of my erratic moods and mini-meltdowns when I get over-stressed.

I suppose he provides the personal support network I need as a person with AS. He loans me tools, gives me salvaged materials to use on my projects, and volunteers expertise on construction techniques. In retrospect, it is obvious that I surround myself with people who possess the organizational, and sequencing skills that I seem to lack.

Owning rentals has not been easy work; the hardest part has been learning to overcome the fear of things going wrong. Ironically, lots of things have gone wrong, I’ve had tenants arrested, flood outs, tenants have died, people have fallen on ice in my parking area, but when these things happen they were never as hard to take care of as I had imagined.

Emergencies seem to make me focus and transcend my ADD, and the adrenaline over rides the difficulties I normally have with AS. I’ve had so many emergencies that now I just figure I’ll be able to handle it. Another AS difficulty that I have is that I don’t enjoy small talk, so on a day to day level, I do find it difficult to interact with my tenants. In my dealings with them I just try to be honest, friendly and professional. They seem to realize I’m a bit odd, but they gradually get used to it.

It has also been hard to take so many financial risks. I’m almost pathologically cautious with money, but as things have worked out I’ve learned to be much less anxious and risk averse. As things have gone well with my rentals, I’ve grown much more confident in my abilities, and know that I could replicate this success in the future if I had to. Much of my anxiety about money is thinking that I wasn’t very good at making it, so I was obsessive about conserving it.


Being self employed has allowed me play to my AS strengths. I have very little desire for conspicuous consumption, and no desire to impress others with shows of material possessions. This has enabled me to live very modestly and to put back all of the revenue generated by my properties into the business.

Pouring money back into the properties made them financially secure very early in the process, and this has really reduced my anxiety over making such large investments.

My fascination with numbers has allowed me to assess the value of properties and base my real estate purchases on sound business principles. My obsessive sense of honesty and fairness has allowed me to treat my tenants in a manner that pleases them, and consequently, I have very low turn over in my properties.

Unlike working in the hierarchy of an established company, which can have many layers of social interaction, I enjoy the relative simplicity of owning rental properties. Although personal interactions do play a role in being a good landlord, the exchange is a fairly straight forward one. I have no boss, and although I’ve made plenty of mistakes, none of them have threatened my position, or financial well being.

Another AS factor has also helped with my self employment, and this is my position as an outsider. Like many people with Asperger’s, I’m not that connected with the culture I live in. This has let me stand out side of the normal workings of society and formulate a job to suit my own needs. I had a clear vision of wanting to be self employed and haven’t let the judgement of others stop me. I have also been able to utilize the resources of my friend Dave, and the clerical, and judgement skills of my wife, to help me make up for some of my organizational and record keeping deficiencies.

I find that there are some downsides to being self employed. My strong need for security and my anxiety over money have been constant nagging concerns. These concerns have slowly abated as the properties have increased in value and cash flow.

Another problem is that I’m constantly “on call”. If something goes wrong it has to be addressed immediately, or I find it very stressful. This is particularly disconcerting while I’m on vacation. I combat this by having ample savings, to take care of problems, and by having people I can trust to handle technical problems, like electrical failures or dead furnaces.

My renters really appreciate how soon I take care of problems, but I find it very uncomfortable to have a problem persist for very long. Another problem I have is working on the apartments while people are home. I find it hard to chit chat for any length of time. I have two strategies to deal with this. I sometimes pay one of my ex-tenants to help me, and this seems to defuse the stress, or sometimes, I just bite the bullet and try to be sociable.

Real estate investing has been a good fit for my personality. It is a career that is very clear cut in its principles and requirements for success. It is work that doesn’t contain a lot of abstractions.

Most of the work can be done by one person and I‘ve learned to tolerate the unavoidable social interactions. I’ve also learned that nothing is worth getting worried about, and tenants really appreciate my low key approach, by expecting the best in them, they almost always come through. I also love to learn about new construction techniques that can be used on the rentals and to deal with the numbers of finance. I keep track of all the loan balances, monitor rental prices and real estate trends.

The last four years have seen real estate prices, as well as rents, rise, and we are doing well with the cash flows. In the next few years I hope to discontinue outside construction work completely, and buy, and fix up smaller homes.

In writing this story I realize how lucky it was that I never gave up on the dream of finding a career that worked with my quirky personality. What made me so persistent was the realization that I didn’t fit into the regular world of work and employment. I had seen others in my family destroy themselves by trying to be what they weren’t, and I wasn’t going to let it happen to me. I would find the life that gave me satisfaction and meaning.

My biggest mistake was letting fear keep me from buying investment properties earlier. It is also fortunate that I have a wife who loves, and supports me, through all the down times, and a friend like Dave to help me with the rentals.

Managing with Asperger Syndrome