During three decades of self-employment, I’ve had frequent conversations with people who express envy for the fact that I’m my own boss.
In these chats, it is apparent that many folks believe the grass has got to be greener for those of us who are self-employed. And while that surely isn’t accurate all of the time for every self-employed person, I always tell people that quitting my last job and going out on my own was the best decision I ever made.
Yes, there have been struggles; I’ve had to survive three recessions! But if you’ve done the things you need to do to succeed out on your own, the benefits definitely do far outweigh the downsides.
What I’ve found, however, is that the benefits of self-employment are not always obvious when you’re starting out.
Often a person’s chief motivation for moving into self-employment isn’t the thing that makes them happiest in the long term. Many times, people are stuck in jobs they hate or with bosses who drive them around the bend and that’s why they walk out the door. That was certainly my case.
But what ended up making self-employment so satisfying had nothing to do with not having a boss, because in reality when you are self-employed, you have numerous bosses – your clients or customers.
Here then are seven significant benefits of self-employment, some of which you may not realize until you’ve been out on your own for several years or more.
Table of Contents
- 1. Choosing which clients I want to work with and those to whom I say, “No, thanks.”
- 2. The freedom to work at home, set the hours, and organize life the way I want it
- 3. Ability to control my own fate
- 4. Having control over the direction your business takes
- 5. Being the decision-maker
- 6. Flexibility in choosing where to locate your business
- 7. Greater control over your income
1. Choosing which clients I want to work with and those to whom I say, “No, thanks.”
As I explain in the introduction to my book, The Self-Employment Survival Guide: Proven Strategies to Succeed As Your Own Boss, my last days as someone else’s employee were spent working for a Boston public relations firm.
There I sometimes found myself sitting across a conference room table from a client I didn’t much like. This in part happened because most of that firm’s business was with real estate developers. Some of them were great—even inspiring—people.
But that industry also seemed to attract a disproportionate share of egomaniacs. Or at least that was the case during the real estate boom that Boston was then experiencing at the time when quick-buck artists were plentiful.
Also, I’ve never met anyone who would haggle over price than a real estate developer. They wanted maximum results for a minimum dent in their budget.
One night, I found myself driving home around eleven o’clock from a town meeting at which our clients were trying to get approval for a small project. It was snowing like crazy on the major highway I was on, and all I could think of in the near whiteout conditions was that I was going to drive off the road, go down an embankment, and not be found for hours.
The fact that the developers in question were not very nice people hardly made me feel better about my impending demise. These were not people I would have chosen to work with if I’d had an option. (And yes, I do realize this is easy for me to say; I wasn’t the one who had to sign the payroll checks every other week, so I can’t really criticize the agency owner for agreeing to work with some clients who had money but no manners.)
Since becoming my own boss, I have had the option of saying yes or no to any prospective client. When I turn down business because I don’t think the personality fit is right between the prospective client and me, the sense of freedom is great.
It’s so much easier and more motivating to work with clients you really like than with clients you’d prefer not to be around. So I ask myself, “Would I like to hang out with this person?” If the answer is “No, I wouldn’t particularly care to have lunch with him/her,” then I usually take a pass on the business.
2. The freedom to work at home, set the hours, and organize life the way I want it
I am a night person by nature, so having the choice to not get out of bed at the crack of dawn, get gussied up, and commute to work suits me. If I feel like sleeping in, I do. Sure, I may work longer in the afternoon or evening to make up for that extra hour of sleep in the morning, but for a night owl like me, it’s worth it.
And if I decide to take Fridays off in the summer, nobody is going to say, “No, you can’t do that.” The same is true for picking my vacation weeks.
This control over my time also means I can go to the gym or go grocery shopping in the middle of the afternoon when these places are much less busy than they are if you have to go after work or on the weekends.
I also can take time off during the day to volunteer, or, if the writing muse just isn’t with me on a given day, I can grab a book to read, go for a walk, or do anything else that strikes my fancy. Also, I spend my summer days barefoot and wearing shorts and a T-shirt and my winter days in jeans and a fleece top.
Once in a while, I do have to go meet with a client, but people nowadays are quite happy to work via phone and email. I even have several clients in faraway locations who I’ve never met, including one in Denmark with whom I have written several books. Technology is grand, isn’t it?
Related: How Has Technology Changed Our Lives
3. Ability to control my own fate
This is perhaps the biggest benefit of being self-employed. When you are working for someone else, they ultimately decide what direction your career is going to take, how far and how fast you are going to rise up the career ladder, or whether you’ll get kicked to the curb.
For the first ten years or so after I left corporate life, I wondered if I’d made a serious mistake. I was living in Boston at the time and had plenty of friends who worked at big companies where I knew they had nice benefit packages. I once had those same kinds of packages—great health insurance for next to no money, a good pension plan that my employer contributed to, four weeks of paid vacation, profit sharing—the works.
Then bad things began to happen to my friends. For example, when Polaroid was driven into the ground by bad management in 2001, I had several friends who lost all the money they’d invested in Polaroid stock through the employee stock ownership plan.
Not long after, the life insurance company where I had worked for eight years was bought out by an industry giant, and jobs were lost left and right. At the time, I thought about how that could have been my fate if I’d stayed on there.
And this continued into the Great Recession. I got a phone call from a former colleague and longtime friend who had worked at Fidelity Investments for well over a decade. She had lost her job and started her freelance writing business up again in the middle of one of the worst economic downturns ever. I felt very badly for her at the time, although I’m happy to report she managed to do just fine.
Because of events like these, I stopped envying my friends in corporate life long ago. Yes, it has been challenging to be self-employed through three recessions. And, sure, I sometimes wish I didn’t have to pay the whole Social Security tax without help from an employer. But the joy in knowing that my fate is in my own hands and not in someone else’s is worth all of that and more.
4. Having control over the direction your business takes
Back in 1999, after I’d been self-employed for a decade, I felt the need for a new intellectual challenge. So I decided I wanted to ghostwrite business books. This involved taking a significant risk of devoting hours and hours of unpaid time to write a book proposal and sample chapters with one of my clients. Then we had to find an agent and a publisher, neither of which is easy.
But getting that first book published enabled me to begin pulling in more book ghostwriting assignments, several of which were among the most lucrative assignments of my self-employment career.
Related: How to Become a Ghostwriter
If you’re working for someone else, your ability to change up your career direction like this is limited. In most companies, you have to fit yourself into the job your employer wants you to do rather than being able to choose the direction in which you want to take the job.
You can, of course, opt to find another employer, but this can be easier said than done, especially if the direction you wish to take your career is significantly different from your prior experience. If, on the other hand, you’re self-employed, you are the master of what you will do as long as you can find a market for it.
5. Being the decision-maker
Just as you can choose to take your business in any direction you want to, you also are in charge of every other decision regarding the business and how it operates. Not that you will necessarily always get every decision right. I know I’ve made mistakes along the way; everyone does.
But at least you won’t be at the whim of someone else’s bad judgment, and you won’t have a micro-manager looking over your shoulder and second-guessing everything you do. I can’t tell you how liberating this feels when you fully realize that you don’t have to answer to anyone.
Of course, there are people who prefer to have someone else make the decisions and people for whom making big decisions is agonizing. If this sounds like you, then self-employment probably is not your game.
6. Flexibility in choosing where to locate your business
I’ve moved the location of my business several times. I moved from one end of Massachusetts to the other in 2002. Then, in 2013, I moved to North Carolina, where the cheaper cost of living will enable me to fully retire. Thanks to the wonders of the Internet and because of the nature of my business, neither of these moves materially affected my ability to keep the business thriving.
When I moved from Boston to western Massachusetts, I kept my Boston clients. Of course, I was only ninety minutes out the Mass. Pike, so that wasn’t much of a change, really. But when I moved to North Carolina, I kept my Massachusetts clients . . . and my client in Denmark and my client in Texas and my client in Rhode Island—well, you get the idea.
Of course, not all fields lend themselves to this type of mobility, but plenty does. And while some companies do allow employees to work from remote locations, this option is not yet available to everyone. So if you want to have the ability to relocate at some point, self-employment will give you the ability to do that in many cases.
7. Greater control over your income
Money, money, money. That’s the topic on many people’s minds when they think of becoming self-employed. How to make sure you get paid? Will you be better off financially out on your own? The honest answer is maybe. The variables on this are too numerous to count.
I can only safely share that I made more money in most of the years of my self-employment than any employer ever paid me. And there wasn’t a single year where I made less than the last salary I drew.
But it’s important to also take into account the contributions employers make to essential things like health insurance and that dreaded Social Security payment, that aren’t forthcoming when you’re out on your own. So subtract all that from your earnings and you may some years wonder if it’s all worth it.
Still, the truth is that if you’re willing to put in the effort and you’ve got solid skills and other capabilities needed for self-employment success (networking skills, of course, immediately come to mind) you can meet the financial goals you set for yourself…and perhaps exceed them.
Certainly, you can never walk into an employer and say, “I really need to make $20,000 more this year.” But, you can set in place a plan to increase your self-employment income by that amount (or any realistic amount you choose) and if you work your plan, you can make it happen.
And that perhaps is the biggest benefit of all of the self-employment. It’s all up to you. You are in charge of the fate of your career, not anyone else. What could be better than that?
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