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I Had Four Jobs and Still Fell Behind

Sausha Davis·Aug 11, 2026· 9 minutes

When I was younger, I was always told that if I didn't work hard, I wouldn't amount to anything. Maybe those exact words weren't spoken (maybe they were?) But they were definitely implied.

And I didn't really know we were "poor" until I was older and realized we went without a lot of things most people had.

We didn't have central heating or air conditioning. We cut wood every winter to heat the house. We didn't have cable or satellite TV. We couldn't always just go buy what we needed for school sports. We drove cars that seemed to constantly need something fixed.

We didn't have those things because we couldn't afford them. So it was instilled in me pretty young that you had to work hard. Work hard and you'll be rewarded. And I still believe in working hard. I just don't think working hard and hustling are the same thing.

Hustle culture is always about doing more. If what you're doing isn't working, do more of it. Work more hours. Get another job. Keep going and eventually you'll end up on top.

But you can do a lot of work that never really compounds. I know because at one point I had four jobs. I worked at a bar, a group home, a tanning salon, and a home improvement store. I was literally working all hours of the day, but something wasn't adding up.

If I was working this hard and had four times as many jobs as other people, why wasn't I getting rich?

Why was I getting further and further behind?

Then I got my first corporate job and started learning customer service, sales, marketing, and a bunch of other skills. I climbed the ladder pretty quickly because I caught on quickly. I've always been a fast learner and someone who wants to figure out how things work and how to do them better.

Eventually I was making around $42,000 a year, which was about as much as I'd been making working two or three jobs. Except I wasn't working nearly as many hours. That's when it started to click for me.

I could make more money by learning skills that paid more instead of just working more hours. That didn't mean the work got easier. Those skills were hard to learn. They required math, patience, communication, problem solving, and a completely different kind of work.

I think that's something that gets lost when we talk about working hard. Hard work can be physical. It can also be mental or emotional. And sometimes the mental and emotional work is way harder than the physical stuff.

Sometimes staying where you're comfortable is easier than learning something new, changing your mind, leaving something you've outgrown, or admitting that what you're doing isn't working.

I kept learning new skills and eventually doubled and then tripled that first corporate salary. Again, I wasn't necessarily working two or three times harder. I had skills that paid more. But I was still working long hours, and the mental load was a lot. Then I got pregnant.

I knew I didn't want to be in corporate anymore. I didn't want to pay someone else to raise my kid while I spent most of my waking hours working. So I left. I didn't really have a plan. But I had a ton of skills.

I'd learned sales, marketing, customer service, coaching, consulting, and business. I didn't know exactly what I was going to do with all of it, but I knew I had enough skills to figure something out. So I did.

Within the first year or two of working for myself, I started having $10k+ months working around 30 hours a week. I couldn't believe it. The skills I'd worked my ass off for were starting to pay off.

Yes, I'd put in the sweat equity. I'd put in the time. I'd spent money. I'd learned a lot of shit the hard way. But I started realizing that I didn't have to hustle forever. I've done so many different things in the decade since leaving corporate that I know now you don't have to hustle nonstop to make money.

But you do have to have something people want. A skill. An ability. A product. A location. An experience. Something.

You can't just put something into the world and hope people understand why it matters. And I think this is where the difference between hard work and hustle gets really interesting. Because the answer isn't to stop working hard. It's figuring out what is actually worth working hard at.

I grew up hearing things like:

  • Money doesn't grow on trees.

  • We can't afford that.

  • Rich people are evil.

  • Salespeople are slimy and just want your money.

And yeah, some of those things can be true in a particular moment. Sometimes we genuinely can't afford something right now. Some rich people are awful. Some salespeople suck.

But some rich people are incredibly kind. Some salespeople genuinely want to help people. And not being able to afford something today doesn't mean you'll never be able to afford it.

Money itself is kind of weird when you really think about it. We made it up.

At some point humans collectively decided these numbers on a screen or pieces of paper in our hands mean something. So yeah, it kind of does grow on trees.

The more I've thought about money, the more I've questioned the idea that the amount of money someone makes should have a direct relationship to how hard they physically work. Because my own life showed me that wasn't true.

Four jobs didn't make me wealthy. Learning more valuable skills changed my income dramatically.

Then working for myself changed the relationship between my time and my income again. And now the world of work is changing again.

AI and automation are going to replace some of the things people have traditionally been paid to do. We're already seeing it with customer service, production work, basic administrative tasks, and plenty of other things.

I don't think that means people are screwed. I think it means we need to pay attention.

What are people still going to need another person for?

What are people going to want to experience themselves?

Working with animals. Teaching. Art. Music. Building things. Fixing things. Service work. In-person experiences. Caring for people. Skills that require judgment, relationships, creativity, or an actual human being.

There are probably a thousand directions this goes, and I don't pretend to know what work is going to look like 10 or 20 years from now. But I do think blindly working harder is becoming an even worse strategy. I'd rather ask whether the work I'm doing is actually getting me somewhere I want to go.

That's what has changed most for me. I still want a lot. I want time freedom and financial freedom. I want to go where I want, when I want, with who I want. I want to take care of my family and my animals. I want to experience as much of this life as I possibly can.

And yes, I want money. Not because I want to buy a bunch of shit just to have it.

I want what money allows me to do. I want to experience things. I want to take care of the people and animals I love. I want to have choices. And I want to give back.

I've always given back as much as I could, but I want to be able to do that on a much deeper level. I want to help people who need it without having to first figure out whether I can afford to. Maybe that's why I don't believe in hustle culture anymore.

I'm still ambitious as hell. I'm still willing to work really hard. I'm just a lot more careful about what I'm willing to work hard for. Because I've already tried working more just for the sake of working more.

I had four freaking jobs and it didn't work.

If this has you thinking about your own life

You don't need to quit your job tomorrow or completely reinvent your life.

Start by paying attention.

Look at where your time is actually going.

Ask yourself what you're working really hard at right now and whether it's actually getting you somewhere you want to go.

Look at the skills you've built over the years that you might be undervaluing. What are you really good at? What do people already come to you for? What could you get better at that would give you more options a year from now?

And get curious about your beliefs around money.

What did you grow up hearing?

Money doesn't grow on trees?

We can't afford that?

You have to work hard for every dollar?

Rich people are greedy?

You might still believe some of those things. You might not.

The point is to actually look at them instead of carrying them around for another 30 years without questioning where they came from.

A few books that have made me think differently about some of this:

The Psychology of Money by Morgan Housel

Probably one of my favorites for understanding that money has a lot more to do with human behavior than most of us realize.

Die With Zero by Bill Perkins

This one made me think about what money is actually for. There's a point where endlessly accumulating money doesn't make much sense if you're missing the years when you could actually use it to live.

The Big Leap by Gay Hendricks

More about the ways we can get in our own way when life starts expanding beyond what feels familiar or comfortable.

Essentialism by Greg McKeown

A good one if you're constantly doing more and starting to wonder how much of it actually matters.

You don't have to agree with everything in any of them. I certainly don't.

Read them. Question them. Take what makes sense. Leave what doesn't. See what makes you stop and think about your own life differently.

And if you want to go deeper than doing this on your own, you can see what I'm currently offering and the different ways to work with me at saushadavis.com.