I read from and talk to a lot of people who are unhappy with their situation. You could even say some are miserable. They hate their jobs, they’re exhausted and drained by work and dealing with whatever life is throwing at them. They feel trapped, with no solution in sight.
They want more money, more freedom, more independence so they can do more of what they want.
And in those cases, what I often see proposed as the solution to all their problems is: “I might start my own business” - like it’s the easiest and simplest way to gain control over their life.
I understand the intention and the reasoning. I really do.
But after having done this for over four years now, I’m not sure this is the right solution for 99% of people. I’d even say that for most of them, it would just make things worse.
Don’t get me wrong - for the RIGHT person with the RIGHT reasons, it can be life-changing. But most people aren’t that person.
Here’s what nobody tells you: entrepreneurship is not the easy way out.
And I’m writing this as someone who’s been in the trenches, made the leap, and is still figuring it out.
So let me be clear about something: I’m not anti-entrepreneurship. I did it myself, and I’m still doing it. But I want you to understand what you’re really signing up for.
Why I Did It
Let me start with my story, because understanding why someone jumps into entrepreneurship matters.
In 2021, I had what most people would consider a dream setup. I was living across the street from the beach in Miami, making a decent salary that covered our expenses and more (Rosie didn’t have to work). I had the full trust of my employers. I was working remotely from home in a different country while they were all in France, doing my own hours as long as I was delivering.
I had it good. I had a lot of freedom already.
But here’s what nobody saw: I was bored out of my mind. Every day was the same, blending into the next. I had been with the company for six and a half years, but for the past three or four years, the work was identical - no novelty, not much learning, just rinse and repeat. I didn’t feel challenged. I didn’t feel like I was growing.
I believe that when you don’t grow, you actually regress.
Plus, I had this itch - this burning desire to start something while traveling the world. I was tired of living on the traditional path and conforming to societal expectations.
So I quit. I wanted to chase this crazy dream of traveling the world and experience what only a small percentage of people get to experience in their life. Pure freedom.
I also admit that I wanted (and still want) to prove to myself that I could do it myself.
The Upsides Are Real
I don’t want to paint entrepreneurship as all doom and gloom. Some upsides are undeniable, and they’re the reason I made the leap.
Here’s what entrepreneurship can offer:
Freedom from answering to a boss or manager
Escape from poor treatment or a job you hate
Making your own decisions and following your gut
Managing your own time and schedule (daily, weekly, annually)
Designing a lifestyle suited to your situation and desires
Focusing on work you actually enjoy
Following a passion
Building something with real impact
Growing your own business instead of somebody else’s
Income uncapped by years of experience, title, or company salary grids
Potential for location independence (depending on your activity)
I’ll also add that it’s never been easier. With the internet and our globally connected world, new opportunities pop up weekly.
But easier than before doesn’t mean easy.
Becoming an entrepreneur gave me the chance to embrace a new lifestyle as a digital nomad without being tied to a location (which allowed me to settle in Thailand now that I’ve decided to).
The reason I’m still pursuing this now - even though I could probably make more money as an employee with less stress - is for the freedom. I love being able to start work at 2pm and focus on me-time in the morning, wake without an alarm, change timezones on a whim, disconnect without asking permission. Those points are THE MOST important for me personally.
The Numbers Might Surprise You
Before we go further, let me share something that genuinely surprised me when I did the research.
It doesn’t match what it feels like when you look around (at least in my bubble), but here’s the reality: entrepreneurs represent less than 10% of the population.
There’s actually been a significant decline in people launching businesses over the past 20 years. Yes, there was a spike in 2020 due to COVID (job losses, lifestyle change desires, stimulus checks), but overall, people are taking fewer risks than before.
Interestingly, Gen Z shows significantly higher entrepreneurship rates - the internet generation is fully embracing the possibilities of the connected world.
But here’s the kicker about money: In the US, entrepreneurs make an average of $80K per year. The average employee salary is around $66K.
Is the stress of running your own business worth an extra $14K? That’s the question you need to ask yourself.
Because I’m not making that $80K average. Full transparency: I have not yet - after 4+ years - reached the annual salary I had when I quit. But I also have much fewer expenses, even though I traveled full-time. My monthly expenses traveling or here in Thailand are about equal to what I was paying just for rent in Miami. So all in all, it’s been okay.
The Reality Nobody Shows on Instagram
Now let’s talk about the less glamorous parts.
I’ll start by saying that no situation is ever perfect. No job is perfect. There are pros and cons to everything. It’s life.
People are also different. Some are more suited for certain situations than others.
There isn’t a right answer and a wrong answer - a better or worse situation. Just different options.
My initial take was “entrepreneurship is not the easy solution.” What I meant by that is this: if flexibility, autonomy, independence, and being your own boss don’t matter to you... if you want to be an entrepreneur just for the title and money... I would say, DON’T.
Statistically, you have way better chances of making money being an employee than having your own business. I won’t say it’s like playing the lottery - the odds are better - but still. Most entrepreneurs make less than they did as employees for years.
Here’s what the data shows:
Year 1: 10-20% of businesses fail
Years 2-5: 70% of businesses fail during this period
First-time founders have an 18% success rate
Serial entrepreneurs with prior successes have a 30% success rate
When I saw these numbers, I thought about my own journey. I’m in year 4 now, and yeah... it tracks.
Here’s the reality:
You’ll Obsess Over Money
You will spend most of your time asking yourself: how can I make (more) money? It takes a lot of work, effort, and perseverance to get to a point where you don’t ask yourself this question every month.
My entrepreneurial journey started hard. Rosie and I saved money for a year while in Miami, anticipating it would take time to build our own income. A month after I quit and left Miami, a loved one was in a complicated situation and we decided to help them out financially. We “lost” around $14K of the $20K we had saved.
We were off to a great start before even booking our first flight to start traveling.
So yes, I know what it is to be financially stressed.
Luckily for me (I say that, but it’s not just luck, it’s hard work), I bounced back quickly and was able to make consistent money from there up until fall 2024. It wasn’t crazy amounts - probably an average of $1.5K a month - but it was enough to travel (in addition to Rosie’s income plus low cost of living while traveling). We managed to travel the world for 3+ years without touching our savings while experiencing very unique things. I’m grateful for that.
However, during fall 2024, things changed. When I decided to close my previous business, the online yoga school, I didn’t receive any salary for 5 months. That was frightening, to be honest.
We do have savings we can rely on, so I’ve never been worried to death about ending up homeless and starving. But like most of us, I’ve been conditioned by society to associate my worth with how much I make. Not making a single dollar for 5 months was hard - especially after all the hard work I had put into it.
Why do most businesses fail? Here’s what the data shows:
No market need: 42%
Running out of cash: 29%
Not having the right team: 23%
Competition: 19%
Pricing/cost issues: 18%
Most fail because of poor judgment and decisions. Not because they didn’t work hard enough.
You Won’t Do What You Love (Most of the Time)
When you’re a software developer, you develop software. When you’re a baker, you bake. When you’re a teacher, you teach.
When you’re an entrepreneur, you do everything: start the business and run it with all the admin that comes with it; develop a product or service and price it right; do the marketing to get clients; deliver the product/service; handle design; deal with customer service; manage bookkeeping.
You actually spend very little time on the thing you love doing.
At the moment, I spend 80% of my time doing things other than coaching people or building websites. I probably spend 65% of my time on client acquisition and marketing, and the rest on admin and other tasks. Working with clients represents only 20% of how I spend my time - a few calls a week, emails/texts, and prep work.
(Part of that is because I also set a limit on how many clients I work with at the same time, but still.)
Most of your time, for a long time, will be spent on client acquisition. And if you’re grinding without having “cracked the code” to constantly get clients through your door... it’s a struggle.
Financial Stability Is a Luxury
When you have a job, you know your paycheck is coming. When you work for yourself, you have much less guarantee of that. Some months might be huge, then you might get nothing for a quarter.
During those 5 months without pay, I still had work expenses. I had contractors to pay for the yoga school. But there was nothing left for me (or my business partner) at the end of the month. We kept the business running, hoping it would turn around, but month after month... nothing.
You need to become good at managing your cash flow and planning for the rough months until you reach a point where money flows consistently.
Let’s be real: around two-thirds of entrepreneurs are uncertain about meeting their financial needs.
The Mental Health Toll Is Real
Apparently, 87% of entrepreneurs deal with some mental health issue - constant stress, anxiety, burnout, depression, loneliness.
Remember, the goal was to be your own boss, make your own decisions, have a flexible schedule.
The reality for a long time is different:
Making all the decisions without knowing if they’ll be right is extremely stressful
Your flexible dreamy schedule means you work all the time because you have to grind to get there, otherwise you won’t get paid
Being your own boss? You’re trading a manager for clients who won’t always be easy to satisfy and might “poke” you more than your manager did
Your coworkers and managers might have been a pain, but the structure allowed you to focus on what you knew. Now there’s only you. You have to do it all, whether you know how to or not. Good luck.
And as much as working by yourself can be fun, it can also get very lonely. No one to bounce ideas with, no one to meet at the coffee break, no one to back you up when you have a decision to make, no one to hide behind, no one to fix this damn problem you’re stuck with.
You work long hours, you’re stressed, you might see your friends less because you have other priorities and less budget. They won’t understand what you’re dealing with. You’ll be irritable, which will impact your household and the people you share it with.
Those are the things you don’t see on Instagram stories when influencers try to enroll you in a course to “change your life and take charge of your destiny with this once-in-a-lifetime opportunity.”
Following the closure of my yoga school, I was really lost. I didn’t know what to do to bounce back. I felt lost, lonely in my own head, numb in some ways. It was something I had never experienced before. I had spent 3 years building the school, and it ended with no pay for 5 months and a closed business.
Starting over from scratch was really hard. I had no audience. I was frustrated, down. It took a lot to get back up and put together my new coaching service.
I shared openly that I was considering giving it all up and just getting a job because I was getting tired of the instability and energy it took. I actually applied to a few jobs. The first quarter of 2025 was definitely my hardest moment.
There have been moments I felt like an idiot for leaving that Miami setup.
Clients Become Your New Boss
I’ve been lucky with my coaching business so far and have been working with wonderful clients (I mean it - I’m not just saying that because they might read this).
But I felt it with the online yoga school. Ultimately, whatever you do, you have to deal with people’s emotions and desires. As an employee, you deal with managers and bosses. As an entrepreneur, you deal with prospects and clients.
I’ve always done my best to satisfy my clients, but sometimes I had to deal with clients unhappy with the services we offered, or clients who had something happen to them and asked for a refund. It’s stressful.
Sometimes there was nothing I could do to “fix” the problem. I couldn’t always refund clients because the cash flow was tight and I didn’t have the funds (that’s where proper contracts are essential to protect you as a business). It’s hard.
As annoying as it is, you have to stay professional, suck it up, stay polite even if you disagree. I knew I hadn’t done anything wrong - I just didn’t meet a client’s expectation, which can happen. But I couldn’t control their expectations. We had terms and conditions supporting us, but it’s unpleasant. At the end of the day, it comes with the job.
It’s never fun to disappoint people, especially when you’re really doing your best.
I admit though that the majority of people are nice and lovely. And when I say the client is the boss, what I mean is that instead of answering to your boss, you answer to them. If you don’t deliver on your promises, they will complain (rightly). So you have to meet standards, even if no one is watching over your shoulder.
So Who Should Actually Do This?
I don’t think everyone should pursue entrepreneurship.
If you’re chasing money, you can get a very good salary by educating yourself and picking the right career and company. You might not become a millionaire, but you can live a comfortable life - a life with boundaries between work and personal time.
If you’re chasing more independence, maybe look for remote work, or simply ask your current employer what’s possible. You might have a nice surprise.
I think you should chase the entrepreneurial journey if:
You have a very, very, very (very) strong WHY.
Because when it gets hard (not if, but when), when motivation hits an all-time low and stress is high, you will need a super strong why to remind you why you’re pursuing this crazy thing.
Reflect on this: If you made $0 for 6 months straight but still had to show up every day to build your business, would you still want to do this? If the answer isn’t a clear yes, reconsider. What would make it worth it for you beyond money?
You’re patient.
Don’t expect overnight success. You’ve got to be in it for the long run. We’re talking years here, not months, not a single year.
Reflect on this: Can you commit to 3-5 years of building before seeing significant results? What does success look like for you in year 1, year 3, year 5? Be honest about whether you can sustain the journey that long.
You have this itch you need to scratch.
You want to know if you’re capable of it. You want to challenge yourself and are willing to get uncomfortable, deal with unenjoyable emotions, “get punched in the face.”
Reflect on this: What are you trying to prove to yourself? Is this about external validation or internal growth? What would happen if you never tried - how would you feel in 5 years?
You’re willing to deal with your fears.
You will be judged and criticized by people around you. Be ready for it.
Reflect on this: Who are you most afraid of disappointing? What’s the worst thing someone could say about your decision to go solo? Can you live with that criticism? How will you handle doubt from people you care about?
You’re willing to deal with instability - especially financially.
Don’t be reckless, especially if people depend on you. Please, don’t put your family at risk. Plan accordingly.
Reflect on this: How many months of expenses do you have saved? What’s your minimum viable income to cover necessities? What’s your backup plan if things don’t work out? Have you discussed this honestly with anyone who depends on you financially?
You’re resilient and don’t let a loss bury you - because you will lose some battles, most of them even.
Reflect on this: Think about the last time you failed at something important. How did you handle it? How long did it take you to bounce back? What helped you get back up? Entrepreneurship will test this repeatedly.
Why I’m Still Doing This
But I ultimately decided to keep trying.
I am passionate about coaching people. It really fills my cup and brings me a lot of joy. Even though I’m not making the money I was making as an employee, we’re okay, and we have savings in case we have bad months. So I’m not panicking.
I’ve grown a lot in the past eight years and developed good self-awareness. I have tools like daily meditation to help me stay regulated. I trust the process, I educate myself, I know these things require time, effort, and patience.
The freedom is still worth it to me. Waking up without an alarm, starting work at 2pm, having full control over my schedule - these things matter more to me than a bigger paycheck.
But that’s MY why. What’s yours?
Here’s something important: entrepreneurs with mentors are 3x more likely to succeed.
That’s not motivational fluff - that’s data. Having someone who’s been through it, who can help you avoid the mistakes they made, who can give you honest feedback when you’re stuck... it’s the difference between being part of the 18% of first-time founders who succeed versus the 82% who don’t.
You don’t have to figure this out alone.
If you’re considering the entrepreneurial path - or you’re already on it and struggling - reply to this email. I work with people who want to build intentional, freedom-focused businesses without creating new constraints. I’ve been through the trenches, made the mistakes, and learned what actually works (and what doesn’t).
Let’s have an honest conversation about whether this path is right for you - or how to navigate it if you’re already in it.




Really great points all around. Lately, I’ve been reminiscing about the 9-5 hours of my previous life with great fondness. But I wouldn’t have been able to sail the world with that setup. This is the only way I can live the life I want, so that’s a big reason why I do it. However, I refuse to trade my 9-5 for a 24/7/365, which is the reality of lots of entrepreneurs I know. So maybe there’s a cap to how much revenue I will hit or it could further extend my timeline for growth. So grateful that I don’t need to support a lifestyle in a major western city, though. I only need ~$1500/month to thrive out here :)
This is very well put, and I relate a lot to this. Started my own company a couple of years ago, preceded by some "magical thinking" of what entrepreneurship would look like.. reality was so hard! The financial instability I felt (I left my corporate job to pursue this) and the constant anxiety really hit me. Your article will help people put things more into perspective sure.