I miss my salary, but love my freedom

I have to tell you something Reader, I had a “moment” the other day … I almost cried over not having a salary anymore.

My eldest child is in kindergarten now. If you’re a parent, you might know that means we’re winning financially from not having to pay for daycare. But the cost of summer camps is no joke if we want to work when school is out.

As my wife hit me with the numbers, it hit me that this wasn’t an easy “sure” response, where I could return to watching the Bernie Madoff documentary on Netflix (so good). The additional cost of a few thousand dollars was something I needed to think about and plan for. I might even need to watch my own kids for once … the horror.

And at that moment, I mentally went onto LinkedIn and started searching for a job. I started daydreaming about the new Porsche I would buy and the extended weekend business trips.

Then my one-month old daughter threw up on me and I was reminded why I opted out of a traditional 9-5 for 2023.

My Situation

I stopped working full-time in July of 2022. I wasn’t sure what I wanted to do, but I knew I had a child on the way and I couldn’t keep working startup hours. We manage on one income, several rental properties, and my new role as an adjunct professor. But compared to when I worked full-time, we are way down.

Did I mention we just had a second child …

I want to be home and available for my daughter during her formative years, the same way I was for my first child. But having a kid isn't cheap. And while the extra time with both of them can’t be quantified…actually it can (it’s several hundred thousand dollars a year), that time with them is priceless.

In retrospect, I wouldn't have accepted the professorship, even though it's a personal dream of mine. Having only done a few classes, I severely underestimated the work, but even as a remote faculty member, being part of a university and teaching kids is a unique and transformative experience. It is also only possible without the strain of a full-time tech job.

Is freedom worth giving up an income?

As someone who has forgone a salary for freedom of time and effort multiple times and preaches it to others, the 100% honest answer is … maybe.

Just to be clear, freedom isn’t “running your own business”. Being an entrepreneur is work, hard work. And instead of one boss, you have many, whether they are investors, employees, or customers. All of them decide your fate, not you or a performance review.

When I say freedom, I mean working less than ~15 hours a week and letting your desires guide your time. Because it’s hard to be “paid for real”, when you’re “not really working”, this level of freedom comes with a big financial hit. And even if you are already wealthy, you could be wealthier.

If you are a high-salary earner, this is a big difference. We are talking about $100k, $200k, $500k, or more a year in compensation that will go away. Not a small change.

Even though there are plenty of people on the internet (like this guy) talking about freedom and not working, remember that your life is not mine or theirs, and it’s worth thinking about.

The part that gets left out is actually adjusting to not being defined by work. As someone who takes a lot of pride in my career and accomplishments, suddenly you are forced to answer the question “so, what do you do” in a way that can just feel odd and uncomfortable, even if you are “living the dream”.

Embracing frugality … kind of

I always focus on living below my means. It means I always have the freedom to change things or try something new (within reason). Frugal living gives me a buffer in case anything happens to my family financially.

But, I wouldn’t say I’m “frugal” per se. I don’t have a Porsche, but my ride is still German. And while I do fly coach, I fly … a LOT. For years we lived on about 60% of our income, saving and investing the rest. In order to do that, we’ve consistently lived below our peers making the same amount.


The truth is frugality builds wealth. Wealthy people, based on research (e.g. The Millionaire Next Door), are frugal. While a small percentage just make insane amounts of money, most millionaires saved and invested their way to wealth with modest incomes. They don’t have Porsches, they don’t have private jets, they just have millions of dollars.

My favorite example is Warren Buffett. In watching a documentary on him, I learned that he buys breakfast at Mcdonald's on the way to the office. If the markets are down (aka he lost money) he doesn’t get the full meal, to save a few dollars. If they are up, he’s upgrading the coffee. He’s a billionaire …

When I have my moments and yearn for my salary, it’s really a test of my resolve for frugality. I know I have everything I need … but in those moments, I really just want more.

So, what’s better: frugal freedom or commitment with a salary?

I struggle with the answer. While I don’t have a concrete answer right now, I do believe it’s important to ask. It’s also important to recognize that there is an alternative lifestyle that offers flexibility beyond your imagination, but it carries a cost. Most of us never even consider both sides, so you’re already one step ahead.

- Damien Peters

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