Everybody fantasizes about being their own boss. Yet very few people take the leap of faith because they either don’t have an idea, don’t have the financial means, or don’t have the confidence to execute. It took me almost three years of moonlighting on Financial Samurai as a personal journal before realizing I might be able to make enough money to survive off this site.
And that’s the thing. You don’t have to go all-in with your business! It’s not like in the past where you had to set up a brick and mortar shop, borrow money from the bank, buy lots of inventory and equipment, sign a one year rental lease agreement, and hire people in hopes of just making it. Now you can simply start your own business for under a hundred bucks a year on the side.
Early Retirement And Being Your Own Boss
Despite making much less than my day job my first two years of going solo, I was much happier. How is it possible to make 80% less, but feel at least 50% happier? The simple reason is because I controlled my destiny. All I’ve ever wanted was a correlation with effort and reward. I’m sure many of you wish the same thing as well. Very few day jobs provide an absolute meritocracy.
Can you imagine working harder than your peers only to get a 3% raise? How demoralizing! No wonder it’s so easy to lose your motivation after several years on the job. How about seeing loyal soldiers work for years only to get laid off? Not good.
But imagine a scenario where the sky is the limit. I’m sure many of you would work much harder and be much happier if you knew there was a stronger correlation between good work and reward. 100% of the spoils go to you, instead of only 3% to you and 97% to your company and its overpaid management team.
Being your own boss is like a short cut to early retirement. As someone who went through an identity crisis an an early retiree and an online entrepreneur for the first two years, I can say with absolute certainty the feelings of retiring early and being your own boss are EXACTLY THE SAME.
So for those of you who aren’t able to retire before 65, or those who still have a ways to go before retiring early, starting your own business may give you a whiff of what a free life smells like. And for those who retired early, but don’t have the energy to be an entrepreneur, you’re living a similar reality!
Killing Two Birds With One Stone
I now believe starting a website while in retirement is the perfect combination for all retirees. The biggest problem with retiring early isn’t the lack of money, because you wouldn’t be able to retire early in the first place if you didn’t have money. The biggest problem with retiring early is BOREDOM.
For the first year and a half after leaving my day job, I constantly found myself bored by 10am. My writing was done by then and everybody I knew was at work. There were many days when I’d just chill in Golden Gate Park twiddling my thumbs waiting for somebody to show up to play a pickup game of tennis. It didn’t matter if they were terrible, I just needed something to do.
Having a family would instantly cure my boredom, but a family takes time to create. The next best thing is having Financial Samurai, where I can instantly connect with readers every day.
Boredom is not the worst feeling in the world. But if you’ve been used to constant stimulation for years, boredom can really change your attitude for the worse. It’s important to keep your mind stimulated during retirement. Everybody needs a purpose, no matter how small.
You Don’t Have To Register As An LLC Or S-Corp
Another stumbling block people have is feeling like they need to register as an LLC or S-Corp to start a legitimate business. This isn’t true. You can simply be a sole proprietor without a business ID number, just your social security number. All you do is earn income as a freelancer, report the income on your Schedule C tax document, deduct all your business expenses, and pay taxes on your operating income.
The main reasons for starting an LLC or S-Corp are liability protection purposes, dividing ownership, and having an asset to sell sometime down the line. You can’t sell yourself. Well you could, but that would mean you’d be an employee again. I didn’t create my S-Corp until after I left my job because before then, I was just writing purely as a hobby. My book wasn’t published yet and I wasn’t selling anything.
If you plan to moonlight on the side, it actually might be best to not incorporate your company. Many companies have outside interest limitations because they want their employees to focus on their jobs. There’re also business taxes you must pay. But if your business starts gaining traction, you might as well incorporate and take it more seriously. Besides, there’s no limitation to free speech if you were to start a blog.
Finally, if you remain a sole proprietor, make sure you have some type of protection in terms of an umbrella policy so that in the unfortunate case when someone wants to go after you, your assets are protected.
Comparing Work, Early Retirement, And Entrepreneurship
Now onto some more concrete numbers to prove my point that early retirement and entrepreneurship are eerily similar! Based on my experience as a day job worker, early retiree, and entrepreneur, I’ve created this chart comparing the three in the most objective way possible. I rate each of the five variables on a scale of 1 – 10, 10 being the best/easiest and total the scores. The numbers have been crossed checked by a number of other people who’ve experienced all three stages like me.
Go through each and give your own rating. Let me know where you strongly disagree. It’s pretty amazing Early Retirement and Being Your Own Boss both scored the same.
Autonomy: Autonomy can be defined as freedom. Thus, early retirement wins hands down. Entrepreneurship, however, isn’t far behind. When you’re your own boss, you still have obligations to clients. You don’t have to look at your calendar in early retirement to see what’s on deck. Work is pretty horrible for autonomy unless you are the boss in a satellite office.
Fulfillment: Being your own boss is the clear winner because you’re actively doing what you love. Hopefully, people who are in their early retirement phase can also gravitate towards doing what they love due to having more spare time. Volunteer work is extremely fulfilling. So is connecting with people online and sharing your experiences. Fulfillment is why those who are able to retiree early should start their own business. It’s an incredible joy to do something you love when there’s no pressure to make any money. I can see my score of 5 for the Day Job category as being debatable. But even if you raised the score to a 8-10, the total score for Day Job still wouldn’t match Entrepreneurship and Early Retirement’s scores.
Money: In the initial stages, it’s much easier to make money from a day job than it is as an entrepreneur. A paycheck is steady, and hopefully you’ll get raises and promotions. It’s harder to make money in early retirement because you’re not motivated by money. Freedom and fulfillment are your priorities. However, when nobody is pushing you, it’s easy to get lazy. Initially, it’s difficult to make money as an entrepreneur. You need to survive long enough to build a brand and create a loyal following. But once you get over the initial hump, the money is far, far greater than any day job. The richest people in the world are all entrepreneurs, not folks with day jobs.
Difficulty: A day job is a walk in the park compared to being your own boss (9 = easy). Go to work, do some work, do as you’re told, and leave it all behind once you go home. As an entrepreneur, you’re always on call. You’ve got to be the CEO, CFO, COO, and CMO of your business. But that’s the fun part of it! When you’re thinking and working 100% for yourself, it doesn’t feel so much like work. It feels like fulfillment! To make things less difficult, you can hire freelancers to help you with areas you don’t like e.g. taxes.
Happiness: The initial euphoria of getting a job wears off after a year or two. Sooner or later, a job becomes mundane due to: office politics, a poor correlation between reward and performance, repetitive work, envy for those who make much more, and exogenous variables outside of your control. Early retirement life is filled with happiness due to having 100% autonomy. You’re spending time doing whatever makes you most happy because you can. As an entrepreneur, you’re happy because you have a lot more autonomy to do what you want. If you start feeling your business is losing purpose, you can always pivot.
The best combination really is to moonlight while having a day job. Second best is to do something entrepreneurial once you are able to retire. And if you can have a spouse earning a steady income while you go after your idea, well, all the more power to you!
Freedom Is Much Greater Than Money
I’m glad I spent 13 years in Corporate America. If I didn’t, I wouldn’t be able to truly appreciate how awesome being my own boss is. The difference is night and day, and that’s coming from someone who enjoyed his job ~75% of the time and made a very handsome salary.
Progress is my one word definition of happiness. When you own your own business, there’s an endless amount of progress to be made!
Interested in starting your own website? Check out my step-by-step tutorial guide on how you can launch a site like mine in under 30 minutes for just $2.95/month. A website legitimizes your business and becomes your online portal. Not a day goes by where I’m not thankful for starting Financial Samurai in 2009. In just 2.5 years, I was able to quit my job and be free. Everyone should leverage the internet to build a brand, build a business, and become untethered from an office to live a life of purpose!