How Employee Benefits Get Better When You Work For Yourself

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A couple of years ago I unexpectedly lost my full-time job. Instead of looking for another position where I was trading time for money, I decided to try entrepreneurship.

In some ways, it wasn’t easy. I had to manage the emotions of a major setback while working smarter than ever. But in other ways, it was a lot easier than I had expected.

I’d wanted to quit my job, and had a fairly simple plan to do so and keep my full-time income. I just had a little push into it much sooner than I had anticipated. 

That ended up being one of the best things for me because it’s easy to get paralyzed by the comfort of “employee benefits.” But I quickly learned after starting to work for myself that these benefits are better when you leave the 9–5.

Here’s how my benefits actually got better after I started my own business.

PTO is a Scam, Freedom of Schedule is Better

In a couple of weeks, I’m going to Alaska. 10 days after that I’m going on a trip with family. Earlier this year I spent almost two weeks in Hawaii. I regularly take Fridays off for a long weekend of camping.

I can take as many mental health, vacation, or whatever kind of days off as I want.

Oh, and if there’s a huge snowstorm, I don’t have to go into an office. I could if I wanted to, but the lie that your company has to be big is a story for another day.

I can do almost whatever I want, whenever I want, because I work for myself. 

“But what about getting paid to take time off?” you might be wondering. Well, the appeal of that dwindles to nothing when you know how to make passive income. Or delegate work to others like a virtual assistant

The truth is, once you get out of the corporate trap, you start to see ways to make your full-time income in much less time. I did that with my engineering career and began delegating the work. And twice in the last month, I’ve made over $200 in my sleep from affiliate marketing.

So no, I don’t care about PTO. Entrepreneurship is smarter than that. It lets you make money in your sleep and earn more per hour by teaching you how to delegate. And I haven’t even got into the tax benefits.

By far the biggest benefit though is that I get to be home when my beautiful wife and adorable children wake up every day. We get every meal together and I can take long lunch breaks to take them to the aquarium or park. 

Because I work for myself, I’ll get to see so much more of my kids growing up than anybody who goes to an office could ever dream of. That alone is worth being an entrepreneur.

My Health Insurance Got Better After I Started Working for Myself

In 2017 our daughter was born six weeks early and spent two weeks in the NICU. The combined cost for her and my wife was $80,000. 

Our insurance was so bad that we still got a bill for $50,000 even though the emergency situation that made our little girl come early forced us to go to a better hospital. We had no choice, and they still sent us a depression-inducing bill.

Half of that was the wildly incompetent hospital billing department, who, when I asked what we could do said “the best we can do is give you an option to pay $1,600 a month for the next few years.”

Luckily, we got in touch with some unfortunate but benevolent people who have to deal with insurance and hospital monsters more often than most people and know how to get them to be reasonable. 

They helped us work everything out so we didn’t have an extra house payment trying to pay off this already traumatizing situation.

Fast-forward a couple of years and we were having another baby but this time, with the better insurance that comes with working for myself. He was early too, and spent over two weeks in the NICU.

His and my wife’s combined cost was over $120,000. We only paid $1,500. 

Oh, and because we’d hit our out-of-pocket maximum, the surgery to fix his cleft lip later that year cost us nothing.

Insurance is way better because I work for myself. But only because we have a stellar insurance agent as part of our team of people helping us figure this all out.

I can’t guarantee it works the same in every state, but I’ll just say that if it’s possible for me to get insurance this good, it may be possible for you to do the same if you work for yourself.


Did you know that a portion of your 401k goes to paying the people that manage it? And those hidden fees change all the time? They didn’t tell you that when you set it up, did they? 

Why would they though, it makes them a ton of money!

That’s right, the company that takes care of your retirement investment is secretly getting rich by keeping you ignorant. They are also putting all the risk on you but make it seem like you’re taken care of.

What’s worse, you’re not actually very likely to get a retirement-level nest egg by following their advice. You need to save more like 10–15% of your paycheck instead of the 4–6% they usually recommend if you want to retire around 65.

The problem here is that the false sense of security that your 401k gives you is keeping you from actually managing your money wisely.

By giving that up, you also give up the chance to be lazy and put your future in someone else’s greedy hands. Someone else who is stealing your money for doing something that you’re perfectly capable of. And probably better at.

Becoming an entrepreneur forces you to be smarter with your money and your future.

Coworkers and Clients

The one thing I did start to miss a little after leaving the 9–5 was my coworkers. I’m a people person and I really liked talking with just about everybody at work. 

That all went away when I started working from my home, and I felt a little lonely. But that only lasted until I realized that I get to choose my coworkers now.

I’m in an online group of writers and they are some of the best people in the world. I love spending time with them. They always lift me up and I get to talk with them regularly to get ideas and encouragement. 

I also have an awesome mastermind group that I meet with every week. They give me so much more than any previous coworker ever did. And they’re my friends. 

The best part is that I get to choose all of these people and never get stuck with a toxic coworker. If someone starts dragging me down, I can just stop spending digital time with them. And I can go find someone new anytime I want.

The same is true for clients. They say that 20% of the clients bring 80% of the problems. Working for myself means that I can drop that 20% instead of having to hear my boss complain about that one client he wouldn’t let go of because of the money.

Entrepreneurship Isn’t Always Easy and It’s Not For Everyone

I should clarify the title of this section by saying that entrepreneurship might not be for those who were lucky enough to grow up without crazy financial issues like skyrocketing costs of living and stagnant wages. Those who probably also have something more like a pension for their retirement plan.

And maybe you get to work in a job you like that pays you a living wage and then some and lets you work with people you enjoy being around. 

For the rest of us, setting up our own company and becoming a freelancer just might be the best bet. It’s a lot easier than getting startup capital, hiring employees, and going big. Which are the other lies about entrepreneurship that hold you back from jumping into this better way of life for many people.

It really can be as simple as establishing an LLC and doing the work you were already doing at your job, just for clients instead of your boss. If you can find ways to automate it, you can hire virtual assistants instead of employees. You can delegate without having the paperwork mess that comes with actual employees.

In summary, my life is way better now that I work for myself. Those “ employee benefits” that I may have worried about losing are much better than they were at my job. 

This might be the same for you too, but only if you get a good team of people to support you.