Career Advice: 9 Uncommon Reasons to Work For Yourself

105 West Blog - Working For Yourself

I work for myself now.

I quit my cushy corporate job and took the “plunge” into freelance digital work. I, like all of my supporters in the endeavor, believed it was going to be rainbows and butterflies, and some of it has been. But most of it hasn’t. On the contrary, it has been the most difficult thing I’ve ever done.

After two years of grinding, hustling, cold calling, penny pinching, and continuously and hopelessly breaking down over my perceived lack of purpose, I’ve come to the conclusion that I’m a better man for it. Working for myself has been a right of passage. It has taught me values, habits and lessons I never would have learned otherwise. These lessons have made the plunge worth it, whether I come out if it being able to sustain myself or not.

So… here are some the not-too-common reasons you should quit your day job and work for yourself (at least for a while):

1. It’ll teach you how a business works in totality

Unless your office title begins with a capital C (CEO, CFO, etc.), you probably don’t fully understand how your business works. You may know the marketing side, or the accounting department, or operations, but chances are your understanding of the business as a whole is marginal at best. This is a huge barrier to success within the business world. Don’t believe me? Look at the curriculum of an average MBA - it’s mostly intro and intermediate courses to business topics that most people didn’t learn because they kept to their lane.

When you work for yourself you are forced (involuntarily) to learn every single aspect of your business. Hate sales? Too damn bad. Here’s a phone, start cold calling. Don’t know what accounts receivable are? Good luck paying rent in a few months. As the CEO, you need to know every lane of your business in and out, no matter the type of business you run. This is a huge advantage if you ever decide to move back into employment because you’ll understand how your role and your department impact the business as whole.

2. It’ll make you (much) more disciplined

I don’t need to tell you how difficult it is to sit in an office all day and hold your concentration on one task. It’s hell on earth. Now, take away the office and replace it with your kitchen table. Take away the big screen and fancy standing desk. Take away the free coffee machine and the social lounge where you can catch up with coworkers. Take away your boss giving you direction. Now, add Netflix, Instagram, your cat, and your snoring significant other. Add a fridge full of food and those Lucky Charms staring at you from your cupboard. Now, try to do a full day’s work.

Even with coffee shops and coworking spaces, working for yourself without someone else’s direction is extremely difficult. The innumerable opportunities for distraction and the common lack of social interaction make days twice as grueling as they are in an office environment. If you can stay sane day after day of deep work in your own home, you’ll be a superhero compared to your old self. Or, at least, an incredible candidate if you ever decide to go back to being employed.

3. It’ll teach you how to hustle

Think of a time at work when things went wrong. Your team didn’t hit its numbers or the project you were in charge of came in later. What was the outcome? At best, everyone went “aw shucks, next time!”. At worst, someone got a stern talking to and your bonus was reduced. At the end of the day, life went on and you were able to drown your business sorrows in a happy hour pint.

Working for yourself isn’t that fluffy. When you lose a sale or mismanage a project, your livelihood suffers. The immediate and longterm effects of screwing up are completely upon your shoulders. Mistakes feel 100x worse when they affect you directly, and not in some roundabout way like they do at a large company. The only way to recover from subpar results is to double your efforts. Didn’t find enough clients? Search harder and get more creative. Didn’t hit your metrics? Stay up all night and figure out why… then fix it. After some time under this type of pressure you learn that screw ups are fixed with hitting harder and thinking deeper, not happy hour pints.

4. It’ll make you more frugal

Taking money for granted is easy when you have a consistent salary. Notice that I say consistent, not large. It’s easy to let money flow in and out when there’s a steady stream of it because incomes and expenditures become habitual. So, you don’t glance twice at them. Gym memberships, daily espresso drinks, business lunches - all of those things fly under the radar when a biweekly paycheck reaches your bank account.

When you work for yourself, however, money often comes in waves with periods of success and periods of monetary drought. Without the consistency of a salary, habitual purchases carry a lot more weight in your mind, even if your making more money overall. A $5 latté is much tougher to swallow when you haven’t made a cent in two weeks. Plus, unexpected costs appear the moment you leave the office life. You now need a place to work, a phone plan that your company doesn’t pay for, a GSuite account for your business email, etc. Oh, and don’t even get me started on paying for your own health insurance.

The best way to fend off being broke is to know exactly where every dollar goes. If you didn’t effectively keep track of your finances before you quit your day job, you sure as hell will when you do. I could tell you down to the penny how much I spent each month since I quit my job and where, precisely, that money went. I could also tell you at any given point in the month whether my budget will allow me to get a latte that day or whether I should be looking into my tea drawer. More importantly, I’ve come to truly appreciate every purchase. Coffee tastes best when you’ve earned it.

5. It’ll make you a decision maker

Not to badmouth the employee life too much, but when you’re working for someone else your workflow is always point A to point B. You’re told there is a plan/initiative/project and your task is to get that thing done. So, you bust your ass to get from point A to point B in the (usually) most efficient way possible with as little work as manageable. You’re like a bus driver - you have your schedule and your destination, now drive. Going from point A to point B over and over again may make you really good at that linear process, but it doesn’t help you build the skill of decision making.

As an operator of your own business you must not only get from point A to point B, but you must initially decide where point B is. Not only that, but you have to accurately understand where point A is. A mentor of mine once told me that as an employee, your job is to get through a to-do list. As an employer, your job is to determine which items on an endless to-do list are most worth getting done. That decision making process is much more difficult than simply getting things done, and as a result much more valued. When managers refer to the “art of saying ‘no’”, this is exactly the skill they’re referring to. Working for yourself gives you massive amounts of decisions to make and ultimately makes you a strategist more than a drone.

6. It’ll make you healthier

Your body doesn’t live on the same schedule you do. This applies to the totality of your body - your muscles, your digestive system, your brain… none of you works on a set schedule. Sometimes your best moments of concentration are well after 5pm. Sometimes your body wants to eat way before or long after the typical lunch hour of noon. Sometimes you get a burst of energy several hours after a convenient time to go to the gym.

When you make your own schedule (arguably the best part of being self-employed), you can balance what you need to do with what your body wants to do. You can set your schedule up in a way that aids your rhythms instead of counteracting them. You can sleep when you’re tired, eat when you’re hungry, and work out at your peak energy times.

After quitting my day job, I noticed a few things about my body very quickly. I concentrate best early in the morning (between 5 and 10am), completely lose concentration during the early afternoon, and regain the ability to think shortly before the evening. I also have the most physical energy around noon and am typically hungry for lunch around 2 or 3pm. Having the ability to set my schedule around my bodily needs has immensely improved my diet, workout regime, sleep pattern, and generally the amount I get done. Since quitting my job, I wake up an average of 1.5 hours earlier and sleep an average of an hour more. I’ve also shed 12 pounds and have kept that weight off without rigorous effort. Most importantly, however, I feel like I think much better and have a much easier time sitting down and concentrating for long periods of time.

Next time you’re on vacation, pay attention to your body’s rhythms and note how they differ from your typical schedule.

7. It’ll let you travel

I know this isn’t “not-so-common”, but I couldn’t write this post without plugging this in.

The single most frustrating thing about working for someone else is that there is an expectation that you have to stay put. In the age of cheap flights and AirBNBs, this is blasphemy. Since I starting working for myself, I’ve lived in 15 cities across 8 countries and have taken a dozen other week-long trips across the globe. And I still spent less, on average, than I did the years previously living in one city in the U.S.

When you learn how to manage your business from a computer, there’s nothing holding you back from travel. There’s wifi practically everywhere now and the internet lets you find reasonable flights and accommodation easier than ever. Got a mortgage? AirBNB your home. Got kids? Take them with you. MacBook charger only plugs into US outlets? …

The point is that in the age of extreme mobility, there is no border you can’t cross when you’re working for yourself. On top of that, I’ve found that I work harder when I am traveling. There’s a self-justification that looms in your head that helps you concentrate on your tasks. Imagine, for a second, where you would be more motivated to get incredible work done: in a dreary cubicle without windows or in a century-old coffee shop in Rome? Hint: I’ve never had trouble waking up at 5am in Italy.

8. It’ll give you a story

Picture yourself at a new job orientation. You know, that meeting where you’re sitting in a circle with a dozen other strangers answering questions you’ve never even asked yourself. The worst question of all comes up: tell us something interesting about you. Never again do you have to be that one individual with nothing significantly interesting to say. “I once ran my own business and failed miserably” sounds a hell of a lot better than “I have two cats named Snickers and Fritz,” doesn’t it?

Even more importantly, it’ll give you a boost of self respect. Every day, no matter how poorly business is going or how down in the dumps I felt, I’m able to say “unlike most people, I tried it. I had the courage. I can be proud of myself for the rest of my life.”

9. It’ll eat at you until you do

Face it. At the end of the day you don’t have a choice. If you’re reading this far into this article, chances are you’ve considered going solo yourself. And if that’s the case the dream isn’t going to magically disappear. You’ll sit in your cubicle day after day thinking about it. If your jealousy towards your Instagram feed doesn’t kill you, your indecision will slow you down so much that you’ll end up getting fired from your day job anyways. Working for yourself may not be for you. Nomad living may not be for you. Business ownership may not be for you. But you’ll never know until you try.