The Solo Supreme

Years ago, I had an acquaintance. He was a “serial entrepreneur” forever working on startups, while his wife worked a corporate job in middle management. When I asked them why that was the case, he said that one of them needed a “stable” job so the other could “take risks”. While I agreed with their reasoning, I thought they had it backwards. They thought it was riskier to work for oneself rather than work for others, and I wondered where that belief stemmed from.

There is this notion quite rampant out there that working for others is safer and more secure than working for oneself, but isn’t there more risk involved in entrusting our future and stability to others? When you work for someone else, you are wholly at their mercy and could be relieved of your duties at any time. You have no say in the matter.

Maybe this idea of having a “secure job” goes back to our parents or grandparents, who might have worked for a single organization their entire lives before retiring. While it may have been more the norm to work for organizations back then, that no longer seems to be the case, for a variety of reasons.

In fact, most of today’s youth aspire to do an MBA at an Ivy League school so they can then get a top-paying “secure job”, where they’ll spend 60–80 hours a week at work, all while taking years to pay off the debts from their student loans, only to find themselves miserable later on in life. Never mind the fact that they are switching from, say, engineering to business. They think by pursuing both engineering and a business degree, they are “covering their bases”, so to speak.

If this were a video game, they would be completionists.

Venture capitalist Fred Wilson famously quipped that “the three most harmful addictions in life are heroin, carbohydrates, and a weekly salary”. I know of a few people who had top jobs, expensive cars, and fancy apartments, and left it all because they were discontented. While they may have been “successful” from the outside, they didn’t feel successful, despite achieving their goals. They thought there was more to life — and they were right!

It’s a fallacy to think that the external things in our life will satiate our inner selves. I know of at least one person who gave up on the fancy lifestyle and ended up at a hermitage for a few months, where he studied with his spiritual teacher and found his Why. Eventually, he left to volunteer his time and share those lessons with others while taking remote consulting jobs part-time to sustain himself.

I also know of a few free agents who left their jobs and struck out on their own. Their only regret was that they wished they had started sooner. I also know of others who left their corporate jobs, worked in their family businesses for a while, then returned to consulting.

That said, working for oneself isn’t for everyone. Some may still prefer working in a corporate job, assuming they are working 40-hour weeks — but working beyond that, I would question their choice.

When we sign up to work in organizations, we don’t think twice about trading our time for money. Even if you are getting an annual salary, think in terms of how much you are getting paid in hours.

For instance, let’s say you make $120,000 a year in a 40-hour workweek for 50 weeks. Your “hourly rate” will be $60. Is your hour worth only $60? Even if you make $1.2 million a year working in an organization, your hourly rate would still be $600. Let that sink in.

I know of freelancers who charge (and get paid) several thousand dollars an hour, and work no more than 20 hours a week — all while working for themselves from the comfort of their own homes and having maximum discretionary time for doing things of personal interest and being with their loved ones. They know that work is simply one aspect of their lives which cannot come at the cost of their personal growth and their relationships.

Here’s the thing: We can either build our own dreams or work for others to build theirs. The choice is always ours, and yet we so often trust others more than ourselves.

I believe that working for myself is the safest and best choice I could have ever made. I would never want to compete in someone else’s “job market”.

Here are some other reasons why I (and others) have found it indispensable to work for themselves and cannot imagine working another way:

  • You have control over your time, which is your true wealth.
  • You can always make another buck, but you cannot create another minute.
  • You work when you want. You are not answerable to anyone but yourself, nor are you dependent on anyone else. Be aware however that there is no one as involved as you in the business, so you won’t have others to act as a sounding board or provide alternate viewpoints.
  • You get to decide who you want to work with; you can’t work with everyone, nor do you want to. (More on this later.)
  • There is no payroll, so you get to keep the profits from your business.
  • You have far less paperwork and reporting.
  • You are the captain of your own ship — you make things happen, period.

Here are some ideas for working solo:

You have to start with the end in mind. You have to find a cause greater than yourself. You don’t simply start a business to make money — that’s merely a result. You have to find your Why. It’s our higher purpose, cause, or belief that inspires us to be who we are at our natural best. By the way, in order to live your Why, you don’t have to start a business. You can perfectly do that while working for others.

Furthermore, the goal of a business isn’t to work with everyone — only those who believe what you believe. That is the one decision you make now that will steer a thousand decisions in the future. It will put you in a “company of one” where you’re not worried about your competition because you’re too busy serving your clients or customers.

Some people think you have to be incredibly self-motivated to work for yourself. While that may be true for them, it’s not the job itself that will keep you coming into work day after day — which admittedly can be monotonous — but the cause you come to work for. This in turn inspires loyalty and attracts others who believe what you believe.

That’s how you find clients and customers.

You need three things to be successful in this arena: You need passionate interests, a high level of skill, and you must meet a true market need (i.e. what the world will pay you for). The intersection of all three is your sweet spot, which will enable you to do your best work. Having only one or two of these won’t suffice — you need all three to make it work.

If you are working for someone else right now, there are two ways you can approach this to get started. You can either 1) use the savings from your day job to fund your monthly expenses for, say, 3–6 months while you hustle full-time, or 2) you can keep the day job and start your business on the side. In the latter case, the time to quit your job is when you start making more money from the side hustle than the day job. If you are in the former situation, you will have to hustle a bit initially to get your business up and running.

When you are a business owner, people expect you to have a real office with payroll. But if you can run a profitable business by yourself, why even bother having all that extra overhead in terms of people and space? Why share all the profits when you can keep them to yourself?

Regardless, you don’t need an office. You can work from home (or anywhere, really). There is no shame in that; I know of quite a few who have healthy seven-figure businesses and work out of their homes. Plus, you get to save on all the extra expenses!

If you do have a need to work with others however, it can get lonely fast. If you need company, get a dog. You will have to find a way to work around distractions at home, or spend additional time commuting to a coworking space to set those boundaries. For some, it’s easier to work when traveling around the world than at home.

Another thing to keep in mind is that you have to do the admin/trivial work yourself if you can’t get someone else to do it for you. And even then, you will still need to hire others — such as a bookkeeper, tax professional, and financial advisor — who can work remotely. Ideally, these should be independents specializing for freelancers. You will also have to get work insurance.

I have always believed that if you have a strong Why, you will figure out the How one way or another. But when you don’t know your Why, no How can get you there. This is true with anything you do. When you want to do something, you will figure out a way to do it. It’s the deciding (thinking) that is the hard part (which is half the battle won). The doing is relatively easier.

It can be incredibly satisfying to work for oneself, doing work that matters to you, pursuing things of personal interest, and doing things together with your loved ones. What more could you want?

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