What It’s Really Like to Work for Yourself

What It's Really Like to Work for Yourself

If you have a traditional office job, my guess is that you’ve at least occasionally fantasized about quitting and working for yourself.

The potential perks are pretty obvious. No boss. Freedom to work when and where you want. The ability to do work you actually care about. The potential to earn more money.

It can all sound pretty glamorous when you’re on the other side. And if you search around online, you’ll have no problem finding people eager to tell you all about how awesome their life is now that they’re out on their own.

I’ve worked for myself for almost three years now, long enough to know what it’s really like, at least at the start. And here’s what I would say about my experience so far:

  1. It’s been one of the most fulfilling and enjoyable things I’ve ever done.
  2. It’s been one of the most difficult and stressful things I’ve ever done.

Here’s my take on what it’s really like to work for yourself.

What I love about working for myself

I’m going to share some of the very real things I’ve struggled with below, but despite all of that there hasn’t been a single moment since I started this business that I’ve wished I was doing something else.

Not one.

There have been many times that I’ve wanted certain parts of what I’m doing to be easier. Or to be different in some way. Or even to go away so I wouldn’t have to do them any more.

And there have been plenty of things that have challenged me in real, profound ways.

It’s been far from perfect. But I’ve never wanted to be doing anything else.

Here’s why.

The work is meaningful

I do work I enjoy for people I care about with an end goal that’s important to me.

I can’t tell you how much of a difference it makes on a day-to-day basis to care so strongly about what I’m doing. I’m so much more excited to get to work and feel so much more fulfilled when things go well.

Simply caring is by far the best part of working for myself. It means that every day I get to work is a good one because I get to advance the mission I care so much about.

That’s pretty fun.

I’m in control

When I have a business idea that feels important or exciting, I get to try it out.

I don’t have to ask permission. There are no politics to navigate. No egos to stroke, other than my own :). No one to chew me out for taking a risk.

It’s empowering to have that kind of autonomy. It frees me up to be creative and try things that may not work, but then again just might because I was willing to take a chance.

I love it.

Rediscovering the joy of learning

I was always good at school. If there was a test to take, I’ve always been able to learn enough to get the right answers.

But this has been a whole new learning experience, and it’s made the entire idea of “learning” a lot more fun and exciting.

These days, I learn something because I WANT to learn it. I learn because it’s applicable to my business in some way and I want to know more, not because someone told me that I had to learn it.

It’s made learning a lot more fun. And also a lot more effective, because I get to take what I learn and immediately apply it to real life situations with mixed results. There are no “right” or “wrong” answers, which makes it both more challenging and more interesting.

This has been an unexpected benefit. I’ve found that my natural curiosity has peaked in a lot of new ways since starting my business, and that’s been a lot of fun.


This is one of the classic reasons people want to work for themselves, and I’ve definitely appreciated it.

Simply put, I have a lot of flexibility around when, where, and how my work gets done.

I obviously have to spend a certain amount of time working, just like anyone else. That’s the only way things will actually get done.

But there’s no office to report to with hours I’m expected to be there. There’s no set allotment of vacation days. No one cares, or even knows, how I’m spending my time or where I am most of the time.

Which means that I get to do things like:

  • Stay home with my kids when they’re sick
  • Spend two weeks in the summer and two weeks in the winter visiting my family in Boston
  • Pick my kids up from school on Thursdays and spend the afternoon hanging out with them
  • Work out in the middle of the day
  • End work early because I’ve finished all I wanted to do

All of this can be difficult too. I’m the kind of person who feels most comfortable in a routine, and when that routine is interrupted it can stress me out. Sometimes a lot.

But on the whole I love that I get to choose how I spend my time, and that if there’s something I want to do, I can move stuff around to make it happen.

The struggle of working for myself

That was the good stuff. But it hasn’t all been easy.

I said at the beginning that this has been one of the most difficult and stressful things I’ve ever done, and I meant it. Here are some of the challenges I’ve experienced.

Am I sacrificing my family?

Maybe I’m just romanticizing the past, but I remember sitting with my oldest son when he was a baby and just watching him play for long stretches, interacting with him when he wanted, and otherwise just observing. Those are really happy memories that I think helped us form a strong bond.

These days (and this is horrible to admit), I often find myself daydreaming about checking my email during family time. Or I’ll start thinking about the next blog post I want to write, or a new process I want to implement in my practice. All while I should be enjoying the precious time I have with my family.

And I hate myself for it.

Now, I love my family and I know they love me. We have plenty of good moments together, many of which never would have happened if I was in a traditional job with traditional hours.

But I do worry that my business is, at least in some small way, hurting my relationship with them. It’s a constant struggle to put my work to the side so that I can focus on them, and that’s something I need to get better at.

Lots of rejection

If you want to work for yourself, you’d better be prepared to get rejected.

A lot.

Every yes is preceded by a string of no’s. Every idea that works is the result of multiple ideas that didn’t. Even people who really like what you do often say no, simply because it’s not the right time or right opportunity for them.

The constant experimentation to find what works can be a lot of fun. The challenge is part of what makes the successes so fulfilling.

But the constant rejection is tough. In fact, many entrepreneurs struggle with depression because of it.

For better or worse, my self-esteem is tied in part to my business. When things are going well, I feel great. And when they aren’t, I don’t.

It can be a tough roller coaster to ride.

Money stress

I started this business after losing my last job. At the time I was my family’s sole income earner, we had a 1-year-old boy, and our second was due in about a month.

We had enough in savings (outside of retirement accounts) to cover our expenses for over a year. And it was a good thing too, because it took a long time before things started to feel even remotely comfortable on the income side of things.

It’s only recently that my wife and I have been able to consistently cover our expenses every single month without dipping into savings. And even now our income varies month-to-month, which makes it hard to make any concrete financial plans.

We’ve never been face-to-face with not making rent or anything like that. But it’s been stressful to have so much financial uncertainty, especially during those couple of years when we were relying on savings and didn’t know for sure whether we’d ever make enough from our businesses to support ourselves.

Working for yourself can eventually be very profitable. But it’s not guaranteed to work, and even if it does it’s likely to be a stressful financial experience for a while.

It’s still work

Chase Reeves of Fizzle is fond of saying that everything becomes a job at some point. And I’ve definitely found that to be true.

I genuinely love what I do and I’m incredibly grateful that I get to do this for a living. There’s nothing else I’d rather be doing.

But it’s still work. It still has plenty of mundane moments, plenty of tasks I have to trudge through, plenty of things I procrastinate on because I’d rather not do them at all.

So when you daydream about the wonders of working for yourself, realize that no matter how much you like it, it will still be a job. Hopefully a good one, but like any other job it’s not going to be fun all the time. Anyone who says otherwise is lying.

I wish this pain upon everyone

Jude Boudreaux has described entrepreneurship as the highest of highs and the lowest of lows, often occurring in the same day. And that about sums it up.

When you genuinely care about the work you’re doing, the high moments are higher than anything you get in a regular job. They’re the result of countless hours of work, countless things you tried and failed, and when you finally get that “yes” it’s just about the most triumphant feeling in the world.

But the flip side is the hours of work, the countless things you tried and failed, and dealing with all of that stress long enough to get to the good stuff.

So, would I recommend making the leap and working for yourself? Based on my experience, and those of the other entrepreneurs I’ve met along the way, I would say yes as long as you meet two conditions:

  1. You genuinely care about the mission behind your work. That, more than anything else, will sustain you through the tough parts.
  2. You have a financial foundation that gives you plenty of time to figure out the income side of things. Because that’s not likely to come quickly.

If that’s you, then I say go for it. Because even if it doesn’t work out, you’ll almost certainly be better off for giving it a shot.

Just know that it will be tough. It will also be exciting and empowering, but it’s not a glamorous ride straight to the top like a lot of people make it out to be.

And if you’d ever like to talk it over, to see if this is really something you could explore, feel free to reach out and let me know. I’d love to hear from you!

Start building a better financial future with the resource I wish I had when I was starting my family. It’s free!

6 Comments... Read them below or add one of your own
  • Ree Klein September 14, 2016

    I loved reading this post, Matt. I could have written a very similar post (except for the kids part) because my experience has been very similar.

    My “service” is actually product based; physical products. But the trial-and-error process and the highs and lows are the same. Things you think will sell great don’t and those you aren’t sure of can.

    I also suffer from the shiny object syndrome, which means I’m juggling several projects all at once and spreading myself too thin.

    But the journey is amazing and I don’t regret my choice to pursue building my own business…even if it eventually ends up a total fail. I’ve been working at this for nearly three years and have yet to generate enough income to even feel comfortable taking a draw from my business accounts.

    So you are dead right…anyone thinking they want to pursue being a entrepreneur needs to wrap their head around doing so while working a traditional job or have built up a sizable financial runway to get them through a couple years of living expenses.

    Here’s to success and loving the journey!

    • Matt Becker September 14, 2016

      Thanks for sharing your experience Ree. And I like your point about “shiny object syndrome”. There’s a lot of value in pivoting at certain points but you need to be careful not to constantly chase new things too, both because you’ll stretch yourself thin as you say and because any good product or service will take time to build and will hit rough patches. Dedication is key, though definitely not always easy.

  • Andrew@LivingRichCheaply September 14, 2016

    I enjoyed reading this post and seeing how things are going. I was always intrigued at your journey since we started blogging around the same time, both have 2 boys, from the Northeast…and I also considered getting my CFP. I often fantasize working for myself and probably idealize it…since there are also the struggles that I never think about. I’m also not sure if I’d be cut out to be a entrepreneur…or maybe I’m just too scared to make that leap. Also, my government job with good benefits and pension is a bit of a golden handcuff! Anyway, I wish you continued success on your journey!

    • Matt Becker September 14, 2016

      Well, to be honest I had a lot of inertia at my old job too and was lucky in a way that I was forced out of it. This was something I had wanted to do for a while, but I didn’t actually do it until I no longer had a job to hold me back. So I can definitely relate to the golden handcuffs and to the fear of not being cut out for it. I’m actually not sure that fear ever goes away. It’s just a matter of pushing forward anyways because you believe in what you’re doing. At least that’s been my experience.

  • Adam@CrispyCabbage September 20, 2016

    Great insight, Matt! I really appreciate this honest look at your entrepreneurship journey. Especially the struggle with family time and giving full attention piece. This hit home with me. Yes, plenty of corporate men and women take their work home with them, but those of us blessed with a good paying 9-5 that can more or less be left at the office, often times don’t know how good we have it. We idealize entrepreneurship too much not realizing there might actually be a different kind of sacrifice to family time because of the hard work and attention necessary to sustain a business. I still want to take the plunge eventually, but articles like these help me stay grounded to a solid plan. Thanks!

    • Matt Becker September 26, 2016

      Thanks Adam! I’m glad you found it helpful and you’re spot on that there’s always a trade-off. Nothing is ever 100% good or 100% bad. Best of luck as you move forward!

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