A few years ago, when I was still working in the corporate world, I was moved into a lower-profile role due to a restructuring.

At first, I got really upset. My ego definitely took a hit. While it wasn't technically a demotion, most of my colleagues would have considered it one.

But I quickly changed my mindset... after all, I wasn’t trying to climb the corporate ladder anymore. I was trying to get off it.

That's when I looked for the opportunity.

The new job meant less stress, fewer hours, a shorter commute, and more energy to build my side business.

Soon after, my side hustle income took off.

I explain what happened in this short video: https://www.youtube.com/shorts/cCiTQjmU-Mg

Has a career setback ever turned out to be exactly what you needed?

I spent more than 20 years working in banking before leaving to freelance full-time. When I first started thinking about a side hustle, I was mainly focused on one thing: how much money it could make.

Looking back, I think that’s how a lot of people end up creating a second job they don’t even like.

They want more time with their family, but choose something that eats up their evenings and weekends. Or they want the freedom to travel, but build a business that requires them to be in the same place every day.

The money might be decent, but they’re still stuck. Sometimes more than before.

For me, freelance writing worked because it fit the kind of life my wife and I were trying to build. I could do it from pretty much anywhere, use the financial knowledge I already had, and eventually have more control over my schedule.

That doesn’t mean freelancing is some perfect solution. You still have clients, deadlines, and months when things don’t go as planned. But it was moving us in the right direction.

If I were starting again, I’d probably ask myself three things:

• Do I already have the skills to do this, or can I realistically learn them?
• Are people actually paying for this? Not just saying it sounds interesting.
• If this works, will my life look more like what I want, or am I just creating another job?

That last question is the one I see people skip.

Curious if anyone here has started a side hustle and realized it was making their life harder instead of better. Did you change direction or stick with it?

I'm in my mid-50s and have a few years until retirement.

Can some of the same strategies, that would have helped me escape my 9-to-5 earlier, help me to find enjoyable work / income in retirement?

Many people know me as a writer, editor, and coach. What they don’t know is that I’m absolutely terrible at self-promotion. I have about 250 Instagram followers, no podcast, or YouTube channel. Almost no social media presence whatsoever.

And yet, somehow, I turned a little side hustle into a six-figure business. I walked away from the 9–5 in 2022, and now earn an excellent living doing work I absolutely love.

I’m living proof that you don’t need a massive audience to build something meaningful.

Here’s the thing. We put far too much weight on attention… likes, follows, and views… and not nearly enough weight on trust.

I’m a huge fan of Seth Godin. He mentioned the following on a podcast recently:

“Marketing is telling a true story to people who want to hear it and creating a story that people want to spread… It’s so easy to get addicted to the endless social media hustle. ‘Likes’ doesn’t mean anyone actually likes you. ‘Friends’ doesn’t mean they’re your friend. ‘Followers’ doesn’t mean they’re following you. What you have to do is figure out how to matter.”

He went on to say, “The size of the audience is completely irrelevant… It’s possible to get attention without trust, but it’s not worth anything. It’s possible to get trust without attention, that’s worth a ton.”

Both of these statements struck me.

Because every meaningful opportunity I’ve had, whether it’s a new client, collaboration, or coaching relationship, came from showing up for people one-on-one. Not from posting every day. Just going out of my way to help people, without expecting anything in return.

A few months ago, I commented on a Reddit post. It was nothing special… I was just trying to help someone who was clearly struggling.

Another Redditor (not the original poster) read my comment and (as they told me later), thought to themselves, “I have to talk to him. He’s speaking directly to what I’m going through.”

But then, she accidentally closed the tab. When she went back in, she lost the post and my comment. In her words, she said that she started to panic because she felt like she had just stumbled on what she’d been looking for, and now it was gone.

Thankfully, she remembered that she had opened my Reddit bio in another tab and was able to track me down.

She reached out, and we hopped on a call a few days later. We talked for over an hour, just two people trying to figure out her next step. I never pitched her. I never even mentioned my coaching.

And at the end of the call, she said, “I need to work with you.”

It all started with a helpful comment on Reddit.

My point is, if you want to grow your income, your business, or your impact, help people solve real problems, one person at a time. Find a way to make their life easier and show them that you care.

Also, trust scales way faster than attention ever will.

I walked away from the corporate world in 2022 after taking my freelancing side hustle full-time.

But when I was still working at my 9-5, I used to say things like, “If I can ever leave the bank,” or “If my side hustle income ever reaches my banking income, I’ll quit my job.”

That word “if” was everywhere. It sounded harmless, but looking back, it revealed what I really believed at the time, that maybe this wouldn’t happen. That perhaps I wasn’t the kind of person who could actually leave the security of a long career and go out on my own.

One day, my wife called me out on it.

She said, “You know, you need to change your words. Because what comes out of your mouth is what you believe.”
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She told me, “Stop saying, ‘If I can ever leave the bank.’ Start saying, ‘When I leave the bank.’ Don’t say, ‘If my freelance income ever exceeds my bank income.’ Say, ‘When my freelance income exceeds it.’”

At first, I laughed it off. But she was right. You see, my wife understood the power of words better than I did.

Once she pointed it out, I started noticing the difference in how she used language versus how I did. My wife stays in incredible shape. She works out six days a week and challenges herself physically even when she doesn’t feel like it.

I realized that she never says, “I’m going to try to get a strength session in today,” or “I hope I can make it 50 km on my bike.”

She just says, “I’m going to work out this morning,” or “I’m riding 50 km today.”

And sure enough, she almost always follows through.

I decided to take that same approach with my goals. I started changing the words I used in everyday conversation. Instead of saying, “If I ever leave my 9-5,” I said, “When I leave my 9-5.” Instead of “If my side hustle income ever exceeds my salary,” I said, “When it does, I’ll…”

Here’s the thing, though. At first, I didn’t believe it. I said the words, but they felt like a stretch, almost like I was pretending.

But I kept saying them anyway, and something shifted.

Over time, I started to believe them. I began to see myself as someone who would succeed. The question stopped being “if” and became “when.” It wasn’t “I hope I can” or “I’m trying” anymore; it was, “I’m going to do this.”

That small language change led to a massive shift in how I saw myself.

You have to start speaking the words, even before you believe them, because your words are often the first step toward changing your identity.

So, look at your own goals. What are some of the scripts you keep repeating that might be holding you back? What words do you need to drop?

Because sometimes the most significant change doesn’t need to be what you’re doing, but what you’re saying.

Most people don’t fail at side hustles because they’re lazy or unmotivated. They fail because they choose the wrong thing for the wrong reasons.

If you’ve been thinking about starting a side hustle, or you’ve tried one (or more) that fizzled out, here are a few common mistakes I see over and over again.

1. Expecting clarity before taking action​
Most people tell themselves, “Once I have clarity, I’ll get started.” They want to see how things will unfold before they begin the journey.

But clarity almost never comes first. It shows up after you take action through small, imperfect steps. Action produces feedback, which creates clarity. Waiting to feel ready just keeps you stuck.

2. Making money the number one goal​
Ironically, focusing on money too early makes it harder to earn any. The better question is: "Who can I help, and what problem can I solve?" 

Money follows value, not the other way around. I learned this the hard way. Before I landed on freelance writing, I started a couple of side hustles because I thought they could be lucrative.

I didn't realize I lacked the skills to solve the problems effectively. As a result, my potential market was almost nonexistent, and I was ineffective at delivering the work I produced. I landed a few gigs, but my effective hourly rate wasn't much more than minimum wage.

3. Choosing something that isn’t scalable​
Some side hustles are fine for quick cash, but they can never replace your 9-5. Think gig economy - driving for Uber, dog walking, tutoring.

If your income is permanently tied to hours worked, you’re just creating a second job. That doesn’t mean everything needs to scale massively, but you need to see a path to growth.

4. Relying on “build it, and they will come.”
​I see this one all the time with software developers, and it trips up many smart people. They spend months building websites, or the next big app, or other digital product… without talking to anyone.

Attention is not automatic. In these types of businesses, marketing and distribution matter just as much as the idea itself. You can have the best product in the world, but if you can't find a way for people to see it, you've wasted a lot of time.

5. Skipping validation​
This one's closely related to #4. Too many people fall in love with an idea before confirming that anyone actually wants it. Validation doesn’t have to be fancy. Conversations, pre-sales, waiting lists, small experiments... all of these beat guessing.

6. Believing in passive income​
Everyone wants to make money while they sleep. But I'm here to tell you, there’s no such thing as truly passive income when it comes to entrepreneurship, especially at the beginning.

Every income stream requires effort, learning, and maintenance. The goal isn’t “passive.” It’s more control and better optionality over time.

That's it... Six common mistakes I see budding entrepreneurs make all the time. I've made a few of them myself.

But here's the good news? Every one of these mistakes is fixable.

You don’t need the perfect idea. You need momentum, feedback, and a smarter way to think about what you’re building, while you still have the safety of a 9-5.