Hi everyone,
this is my first thread here. I’m writing from Italy, and I’m 28 years old.
Important premise: this is not a post of self-pity or complaining. I take responsibility for the choices I’ve made so far and I’m posting to get practical input from people with real entrepreneurial experience.
I work in the private sector, in a standard Mon–Fri 9–5 job. Over the years, I built what I considered a Plan B: degrees in IT and cybersecurity, a private-sector employee role, a house with a mortgage, and living with my girlfriend. The idea was always to use this base to build Plan A: freedom, control, ownership.
The problem is that I kept postponing that “later”: first until after graduation, then after my first job, now to “when I change company.”
Deep down, I’ve always known the employee model wasn’t for me. From the beginning, I never identified with it, even while working in a large, well-structured company. It wasn’t a company problem — it was a model problem.
Recently, things have become even more rigid. The company I work for is not doing well, office presence is constant, and flexibility is minimal. Between that, the mortgage, and living together, it feels like a prison built over time increasingly limiting in terms of control over my time and decisions.
There’s also a strong time factor. At 28, I feel a real countdown related to family and kids. I know that in a few years responsibilities will increase and options will shrink. That makes the conflict between reinforcing Plan B and finally acting on Plan A even clearer.
I also recognize a pattern in myself: I start projects, but I delay finishing them. Finishing means real exposure — the market, real numbers, understanding how much money is actually needed and whether the idea holds up.
I’ve always believed this: you can earn $1k, $2k, or even $10k a month as an employee, become a manager or executive, but if your time is still locked into a 9–5, the model doesn’t change. Income changes, not control.
On a personal level, this model makes me feel like a modern slave / a rat in a wheel — not because of pay or title, but because my time is still owned.
I’ve always been convinced that, long term, the employee life isn’t for me. Yet I’m still not managing to fully escape the structure.
My questions to those with real entrepreneurial experience are direct:
this is my first thread here. I’m writing from Italy, and I’m 28 years old.
Important premise: this is not a post of self-pity or complaining. I take responsibility for the choices I’ve made so far and I’m posting to get practical input from people with real entrepreneurial experience.
I work in the private sector, in a standard Mon–Fri 9–5 job. Over the years, I built what I considered a Plan B: degrees in IT and cybersecurity, a private-sector employee role, a house with a mortgage, and living with my girlfriend. The idea was always to use this base to build Plan A: freedom, control, ownership.
The problem is that I kept postponing that “later”: first until after graduation, then after my first job, now to “when I change company.”
Deep down, I’ve always known the employee model wasn’t for me. From the beginning, I never identified with it, even while working in a large, well-structured company. It wasn’t a company problem — it was a model problem.
Recently, things have become even more rigid. The company I work for is not doing well, office presence is constant, and flexibility is minimal. Between that, the mortgage, and living together, it feels like a prison built over time increasingly limiting in terms of control over my time and decisions.
There’s also a strong time factor. At 28, I feel a real countdown related to family and kids. I know that in a few years responsibilities will increase and options will shrink. That makes the conflict between reinforcing Plan B and finally acting on Plan A even clearer.
I also recognize a pattern in myself: I start projects, but I delay finishing them. Finishing means real exposure — the market, real numbers, understanding how much money is actually needed and whether the idea holds up.
I’ve always believed this: you can earn $1k, $2k, or even $10k a month as an employee, become a manager or executive, but if your time is still locked into a 9–5, the model doesn’t change. Income changes, not control.
On a personal level, this model makes me feel like a modern slave / a rat in a wheel — not because of pay or title, but because my time is still owned.
I’ve always been convinced that, long term, the employee life isn’t for me. Yet I’m still not managing to fully escape the structure.
My questions to those with real entrepreneurial experience are direct:
- How did you actually start? What were your very first concrete steps?
- Are there simple (not easy, but linear) activities that make sense to start with, in sectors with real growth potential?
- Does it make more sense to start with a service, a digital product, something local, or something else given this context?
- Is it smarter to burn the boats — remove the mortgage, drastically lower living costs, and go all-in before responsibilities increase — or to engineer the exit, even if it takes longer?
- How did you evaluate downside risk at a similar stage in life?
- Practically, how did you integrate building an idea or business with a full-time job while maintaining health, consistency (gym), and relationships?
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