5 Life Lessons I Have Learned from Being Self-Employed

For those who have been following, I have spent the past year reflecting on what a half-century of living has taught me. My observations have come with increasing speed as I am winding down my 50th year and fast approaching my 51st birthday.

With just two weeks left until the big day, I realized that aside from gardening, nature, and my family, one of the things that has taught me the most is being self-employed. Here are some of the most important of these lessons.

People often misjudge one another. I have been a fulltime freelancer for nearly 20 years, and most people who have never been self-employed do not understand just what that means. It is even harder for them to understand that I work at home. I know how lucky I am: I get to do work that I love. I donít have to commute, and I donít have to put up with office politics or ridiculous office rules. But that doesnít mean I donít work just as hard as office workers do. I know I work much harder than I did when I worked for somebody else. And I often work seven days a week. Thatís not a complaint, just a reflection of the irregularity that often comes with freelance or contract work.

At first, family members and friends would stop by unannounced to visit without thinking that I was actually working. Even today, some people think that I do not really work because not only am I a farm and garden writer, but I also teach gardening classes. That means I donít have to dress up for my work, and I get paid to play in the dirt.

I can see why some people wouldnít understand. This kind of misunderstanding can cause people to conjure up all sorts of ideas about my life. This is true for many people, no matter who they are. Too often, people envy other peopleís lives, whether itís their careers, their relationships, or even where they live. But, as one of my good friends always reminds me, you canít walk in anybody elseís shoes, and the grass really isnít greener. We all have things in our lives that are hard; we have our own issues, and our own baggage to deal with, we just might not share it or we just might not see it in otherís lives.

Do everything in moderation. This has been the hardest lesson for me to learn. Not just in my work, but in my entire life. †When I first started working from home, I completely overcommitted because I found it so hard to go from a set schedule working for somebody else, to being completely ďfreeĒ to set my own schedule. But, no matter where you work or what you do, there are still only 24 hours in each day. Just because I love my work does not mean it should be my entire life, just one part of it. I try to remember that one of the reasons I chose to work for myself was so that I could enjoy my family and friends more. Ironically, just the opposite has happened. I struggle with this because I forget about balance and get lost in work. This can happen to us in other areas if we donít pay attention.

Always take time to play. This is related to the lesson above. The only ďperkĒ I miss from a traditional office job is paid vacation time. Not only was my vacation time paid, but it was also formally scheduled — and when I was off on vacation, I was totally free. Thatís not always possible when you work for yourself. But you have to make time to rest, to recharge and to enjoy life, no matter how busy. Take time for your personal life, your friends and your family and for yourself. If you donít, you could find them gone and that your work is all that you have.

Learn from everything you do. This has been one of the biggest lessons I have gained from working for myself. I have made some incredibly ill-informed decisions and big mistakes, but I have worked at learning from each of them so that I donít repeat them. And I have learned that beating yourself up for those mistakes only makes things worse. Try to learn what you can from what happened and then move on.

It is never too late to pursue your dream or to start over. If you are passionate about something, ignoring it does not make it go away; eventually it starts gnawing at you so much, that you have to do something about it. I started pursing my writing dreams long before I quit work. In spite of pursuing a masterís degree to get that work, I found it so unfulfilling and tedious that I felt like I was doing time. So, in my mid-30s, I started taking writing and gardening classes, and I wrote in the evenings and on the weekends. By age 40, I had completely embarked on a new career that has brought more joy and fulfillment than I ever imagined.


Kathy Perez
Kathy Johnson4 years ago

this really spoke to me. I am 6 months pregnant, and before I became pregnant I was Assistant Supervisor at a large security company based out of state. I helped run the only NC office for the company, it was an hour drive but well worth it. I loved my job. However, I have a 3 year old and a new baby on the way, and working third was really hurting me. I was always tired and never rested. Sometimes I would be "mommy" on 2 hours of sleep a day for 5 days in a row. When the rough part of morning sickness really hit, my immune system tried to kill me, and I took leave. unpaid, of course. I took one year off work for my first son and loved every moment, and I really hope to do that with this child too. I crochet and have since I was 10. It is my passion. I also make jewelry, quilt, upcycle and scrapbook. One of the things I loved most about my job was that we did 30 minute patrols, leaving the other 30 mins for paperwork and "free" time which we could spend doing whatever. I crocheted :) I want to start a business. I already sell on the side, but want to really go for it. Its a dream.. i am really considering it...

Paul Girardin
Paul Girardin4 years ago


Thanks for putting this article together!

Bryna Pizzo
Bryna Pizzo5 years ago

Thank you for sharing what you have learned about being self-employed.

Chinmayee Jog
Chinmayee Jog5 years ago

Thanks for sharing, very good article :) I especially agree with the last part - I love medicine (I'm an ED doctor), but my passion lies with the environment and animal welfare. I also have wanted to write a novel for years! But everything gets shelved aside due to my work, and I'm finding, in the last 2 years (I'm currently 30), that if I don't make time for my passions, I'm greatly dissatisfied with life in general. Also, yes, always make time to play!

Nils Anders Lunde
PlsNoMessage se5 years ago


Prakash Lewis
Prakash Lewis5 years ago

Thanks for sharing. I can relate to your experience as I worked for companies and then finally decided to work for myself. It is a hard life when you are on your own. You work almost 18 hours a day all week. At the end of the day - Am I happy ? Hard to say.

Michael H.
Mike H5 years ago

Thanks for sharing

Connie O.
Connie O5 years ago

Thanks. I have been self employed for 19 years....and finally am doing something I enjoy!

Debbie Williamson
Solitary Eagle5 years ago

Thank you.

Nicole W.
Nicole W5 years ago

good advice