5 Lessons from 5 Years of Self-Employment

5 lessons from 5 years of self-employment

April 30, 2012 was my last day of employment.

I didn’t anticipate that my resignation would inspire others:

  • Beatrix Wilhelmina, ex Queen of Netherlands
  • Benedict XVI, ex Pope
  • Matteo Renzi, ex Prime Minister of Italy

In five years, a lot has changed both in the world and in my life.

This journey into building a business online has been quite of a rollercoaster. Let me set this straight: I didn’t build a 6-figures business, I’m not crushing it, the traffic on my websites is not server crashing – just to use some popular expressions. But I’m writing this post while traveling in the Philippines, I feel happy and excited about that I do and what will come next.

And in this blog post, I want to share & analyze five lessons learned along the way.


1. It’s all about People

Working for yourself is all about… others.  Yes, working online, without direct human interactions, at first gave me the wrong idea that was all about internet & numbers.

But it’s all about people and here is why:

1.1. A business is an interaction between two people

Nowadays it’s easy to get blinded by the number of visitors, followers, subscribers, likes, interactions, open rate, click rate, return rate, bounce rate, avg. time on page, conversion rate, click-through-rate, etc.

But behind each of these actions, there are real men and women with their needs and emotions (unless you’re in Instagram, then they are fake accounts).

Every business deal is done by two people: a supplier and a customer.

It’s as simple as that. I experienced that in the many travels I did in those past 5 years.
When you deal with a street vendor in a remote country speaking a foreign language, you’re doing business with him.
You negotiate a price, you reach a deal. You’re still two total strangers, but you’re doing business based on a very simple contract: a man-to-man verbal agreement.

This is the way I learned to look at my business: an agreement to honor.
And each contact, email, followers, etc. are people to build a relation with.

1.2. A business is always about helping people

It’s not wishy-washy/do-gooder/enlightenment talk. It is really about finding a problem and a solution for it.
And it’s not easy. It can take very long time to find how.

When I started, I bought some job board websites in Latin American countries. Providing job offers to job seekers is an obvious way to help them, and it worked decently.

But I didn’t know anything about the job market there, and about the problems of the candidates. Instead of focusing on that, I focused on how I could place more advertising, and how I could charge for Premium job posting. This approach didn’t take me very far.

1.3. It’s people work

I did my first two years working alone, doing 100% myself. Then I realized the obvious: I needed to have partners and collaborators.
Working with other was the biggest game changer for me, and it’s a step that everyone sooner or later has to take.
As an entrepreneur, there are lots of things to take care of and to be on top of. It’s overwhelming and I always have the feeling that there’s something I’m leaving behind. A guilty feeling that took a while to ignore. But being able to select the right people to work with, and manage them day-in-day-out, it’s super important.
I’d go as far as saying that once a business is off the ground, working on the team is the most important task for an entrepreneur… more on this later.


2. Forget about Money

Every time I did something ‘to make money’, I failed.

I failed when I took a consultancy for my previous company, thinking that I could make easy money. It was horrible, I could not manage the client and the whole project ended up being a disaster. Knowing that I let down people I worked together in the past made me feel like shit. All of this because I did it just for the money.

Another example is that time I bought a website about drones. I saw good money in it, so I invested $15K.
But I didn’t know anything about drones. I wasn’t even interested in drones. I bought one, I flew it few times. hitting trees, walls, breaking the camera, almost losing it in a park. I hated it.
In the meantime, the website revenues were going down.
Of course, with no passion in drones and thinking only about money, this experience was a failure.
I ended up selling the website for a fraction of the original price, and now my brother has a used drone 🙂

I’ve heard lots of stories of successful people, and I can tell that none of them was in for the money.
Money is a side effect.
Something that happens when you’re delivering value, working with passion and competence.

Actually, I didn’t need 5 years of self-employment to realize that. This was in front of me already during my previous career!
I didn’t become Senior Technical Support Engineer, Senior Network Security Engineer, Professional Service Consultant, etc. because I wanted to make money. None of my ex-colleagues did – even if some stayed for the money.

I just wanted to find my place in society, prove myself that I could be good at something, and have a great job even if I didn’t go to university.
I think this was my drive and, as a consequence, money came. And better jobs, and better money.

The problem is: this sounds like horseshit. We need money to live and this pushes us to do things we don’t want for them. It’s a pity. During the first months of self-employment I was making 200€ and this made me very nervous.

I tried to make more money. It didn’t work. I tried to find how I can help others. I couldn’t. It took a while but again, I’m sharing what I learned and some lessons are only easy when you look back.


3. Screw the books

When I approach something I don’t know, I obviously turn to book. Blogs and podcasts are also great ways of learning, but a good book takes you to an organized journey and is more exhaustive.
The risk is to keep reading books and learn everything without doing anything.

I reached a point in which books were giving all sort of suggestions, principles and let alone techniques about doing just about everything.

I got sick of it.

Maybe it works for you, but I know myself and I have to get my hands dirty and learn my lessons by experience.

Let me go back to my mistakes and my bad logic, don’t feed me the “exact steps” to do something that isn’t replicable like the solution of an equation.

Because my mistake is worth 100 books.


4. Word of mouth is the best marketing

I tried Google Adwords, Facebook Ads, Instagram sponsored posts, sponsoring podcasts, private communities, to a degree of success.
But what works best for me is the good old word of mouth.

You work with one person, if it goes well he’ll send you a friend.
When I say ‘it goes well’ I mean that I gain their trust.

The goal is always to gain trust from customers. Not their money. Not their ‘thanks’. Trust is the strongest bond.


5. From I to WE

As I said before, the biggest change for me was to create a team.
Working with others solved a big problem that I highlighted back in 2014, when I was ‘2-years self-employed old’.

The problem of feeling lonely, working from my living room or somewhere in the world all by myself.

Building a team is a natural step but still, it involves an important mindset shift.

The first person I started working with was Valerio. We’re still working together on one of my blogs, and things are going pretty well. We are similar in some things and opposite in others but that’s good and what’s more important there’s trust.

Again, trust is the foundation of any relation, especially in business.

As WP-OK started taking off the ground, I had to create a small team. It’s a support business, and by its nature can’t be a one-man show!
I remember one episode. While traveling in Myanmar, I was with my buddy Mesut in Ngapali beach, apparently named after Naples (Napoli) by an Italian military stationed there a long time ago.

A customer website got hacked and attacked by a malware.

I had to replace only 6 files to clean the website, but between a shacky 3G connection and electricity outages it took me half day and enough stress to turn my hair gray!

So now you know why I have so many gray hairs 😛

Anyway, that’s not the point.

I built a small team to prevent these situations and I’m really proud of my collaborators: Giacomo and Enrico in Italy, providing awesome WordPress support. Lean in the Philippines, my smart VA that I had the pleasure to meet in person last week in Cebu City. Adeolu and Diego, our writers for RouterFreak. Plus other contractors I work with as needed.

One day last summer, something happened.
I switched from I to WE.
When I used WE in the past, I felt like a fraud because it was only me, really. I’m not good at lying or someone would say in personal branding.

But this time was different: it was a real WE, the genuine one 🙂

We, WP-OK. We, RouterFreak.

It was an important switch but hey, there’s still lots of work and leaning to do on this subject.

For example, I started admiring entrepreneurs who have full-time employees. Hiring a person is a huge step and comes with big responsibilities. I’ll stick to part-time collaborators for the time being.

Overall I’m in a far better mental situation than last year.

This entrepreneurial journey really feels like a winding road unwinding ahead of me. I’m sure I won’t get bored for a while 🙂


Do you relate with any of the lessons I learned so far?


5/5 - (11 votes)

Di Daniele

Hi, I’m Daniele! A human being from planet earth. I founded WP-OK.it and I like dancing Salsa, running, and living a location independent lifestyle.

15 commenti

  1. I think you forgot one important factor: a bit of luck. An old latin proverb says “fortune favours the brave”, and being brave is either a peculiarity of the person, or a life choice. You had the courage to take the plunge and follow your instinct/dream/will, whatever that was 5 years ago. Maybe it was a “calculated” risk, pretty sure you had a safety net, but still a life changing decision bringing you to an unknown (but exciting) path. Well done on your journey so far, and I wish you to keep up your good fortune in meeting amazing people! 😉

  2. A familiar sentiment that hits close to home 🙂 Love this article, it’s a well-written one–with a pinch of humour here and there! Can’t agree more on no. 2 as I have experienced this a lot in life as well 🙂

  3. Great post buddy. Simply great. I can find myself in many mistakes you made…now it’s time to experience your successfully stories too.
    Having the passion for the website/blog subject certainly helps a lot, first of all because you enjoyed it a lot….but probably to make $$ it is not necessary.
    One thing I do not like of blogging is the fact I do not have an office….and I don’t mean it for the 9-5 but more for the 8 to 9 coffees and 6-11…pm…drinks…the real social life…that’s something I miss
    I love your comment about Instagram…lots of bots, as in any social environments, although few weeks ago Instagram has decided to deny access (and basically close) most of them…which is probably normal, same as Twitter did in Jan-2016.
    Great work again!!

    1. Ciao Ste!
      Thanks for your comment buddy 🙂
      I know what I mean, when working from home we had to create our own real social life.
      My father used to work alone in the office just downstairs our house, and every day he would go to the bar at 6:30pm.
      That was his way to meet friends and have social life.
      I’m really curious about Instagram now, I really like it but it became insane how people work around the system to get followers.