Five years of consulting: How it went, so far.

Estimated reading time: about 15 minutes.

Photo by Kekai AhSam on Unsplash

Hi, I’m Davide, I’m an organizational consultant. This is a one-off article I wrote about my five-years (and counting) experience as a freelance consultant. I don’t write regularly in English (which, you might probably guess while reading, it’s not my first language), so I don’t have a significant body of work in English to point you to.

The origin story.

In August 2017 I officially became a freelance consultant. Although, it would be more accurate to say: I registered as a private contractor and then I started to learn what it means to be a consulting professional.

I wanna be clear about where I came from, because it’s a foundational part of the story of how I got here.

It doesn’t have anything to do with money.
It doesn’t have anything to do with how skilled I am.
It doesn’t have anything to do with “having a plan”.
It doesn’t have anything to do with “the hustle”.

When I left my last job as an employee in March 2017 and took months before going back to work:

  • At that point I had changed 4 jobs between late 2013 and mid-2016
  • My father was into the last stage of his terminal illness, he passed away in May 2017

For obvious reasons, I didn’t think my place was inside a company anymore. Not after having tried (and failed, badly) to work for four different companies in the span of the previous three years.

For other obvious reasons — your dad passing away at 58 after seven years of struggles does that — I wanted to be more in charge of how I spent my time.

So not only I decided to become a consultant, but also consulting in a field that I knew nothing about.

I needed a departure.

So the nicest, honest way I would put it is that I really stumbled into consulting.

The reverse 4½ somersault in the pike position.

Namely, the most difficult dive out there.

That’s what I refer to what I tried to do —and still trying to do today— because, you see, a lot of the people who start freelancing they usually follow the path of least resistance, and rightly so: they work in a specific role in a company for many years, and they the start freelancing by doing for clients what they did inside a company for many, many years.

That wasn’t my case.

I didn’t have clear goals.

I didn’t have a plan, or a vision.

I wanted to change path but I didn’t have a direction, or a map, or a weather forecast.

I just had an actually really brief list of things I didn’t want to face anymore at work.

The gist of it: I could avoid those unwanted things only by working outside companies and in a different role.

So I had to become an independent consultant, and, in a way, leave all my previous 12 years of experiences as a business intelligence guy, as a web development guy, as a mobile development guy, as a UX guy, as a project management guy.

I am, by all means, a generalist who’s been trying to emerge in a world that still seems to prefer specialists.

So, I knew that I had to operate outside companies as a consultant in order to find the balance I struggled to find in my previous working experience: but consulting about what?

I’ve been lucky (again).

As soon as I thought I was ready to go back into some kind of action, Marco pinged me.

I don’t remember the pitch, but it was something along the lines of: “we are trying to to bring Agile to HR and make the companies aware that Agile is not just for techies but fundamentally about people and the entire organization”.

It sounded “different enough” from what I have doing up to that point to make me say “why not”, and after a few days I was suddenly alongside Marco, at the table with the CEO of a very well known company, our first client.

A few months after, my first organizational transformation project involved more than 600 people inside a company with thousands of employees. The roller-coaster started.

Bare numbers.

In five years:

  • I trained over 500 people
  • I coached over 35 teams and groups
  • I worked with more than 20 companies
  • I designed and facilitated over 30 workshops, and hundreds of meetings

To me, it feels like it has been 15 years of work compressed into 5, the last two and a half, as you might have noticed, with a pandemic still going on.

It has been a crash course in organizational consulting, team coaching and training people on complex subject such as “how we change the way we work — and, ultimately, the way we think about work”.

At every turn I stumble into something worth exploring and studying.It’ gonna be a never-ending process of learning and getting better.

After years of struggling in finding my place in a company, the realization came quickly: “This is something I can do without getting bored for my entire life”.


For a newcomer like me, consulting has really weird dynamics.

If, like I did, you approach consulting after having worked as an employee for 12 years, you are going to have to go through a long period of adaptation to understand how consulting works, what the rules are, and how you want to play the game.

Consulting firms and consultants get a bad reputation.

Sometimes it feels like everybody hates consultants, but at the same time companies seem to never have enough of them.

By working alongside many consultants, I learn what I am, and what I’m not.

I’m not a suit-and-tie consultant.
I’m not a PowerPoint-wielding consultant.
I’m not into body rental schemes.

It is risky, to have a certain stance about consulting. But it’s my choice.

Companies that have grown accustomed to a “certain type” of consulting can and will see me as ineffective at best, or even a thorn in the side, maybe, sometimes.

In a few paragraphs I will tell you that I’m not good at selling myself, but that doesn’t mean that I’m not crystal clear about what my approach to consulting is.

If you are a CEO, I’m the same as you.
If you are a Head of Something, I’m the same as you.
If you are a Team Leader, I’m the same as you.
If you are a Backend Developer, I’m the same as you.
If you are an intern, I’m the same as you.

I work with you, not for you.

Money, time, energy.

I’ll probably write more in depth about money, time and energy while consulting as a freelance.

It is a huge topic, one of those I never truly reflected upon while I was an employee.

What I’ve come to realize, in short:

  • Energy is the single, most valuable asset you own;
  • Time is a given, a constant, you can’t create it, you can’t manage itM
  • Money it’s not what you think it is, and you should change the relationship you have about it.

As you might imagine, one of the problems of being a freelance is that you are on your own.

Sometimes you feel you are on your own about something that you shouldn’t be on your own about, but other times, let’s be honest, you are really on your own.

I had people saying that I have it easy because I don’t have a boss. I quickly reply that I do have a boss, and that boss is the guy I see in the mirror when I wake up.

And it’s not a nice guy.

Money, in itself, it another huge topic. Long story short: you are sort-of enslaved to it, and you need less of it, but in order to know how much less, you need to start counting things that you never counted before. It will be uncomfortable.

You’ll come to understand that anything you know about money is either wrong, or it was useful when you were an employee, but completely useless now that you are freelancing.

You create energy by taking care of your mental and physical health — more on that later on.

Energy, time and money are the salt, fat, acid and heat of your freelancing career: if you try to maximize or optimize all of them at the same time the result will be inedible.

Weak spots.

Long story short: I’m not great in getting my own clients.

That is not something a consultant should say in his or her website, but I again, maybe I’m not that kind of ego-driven consultant.

The reality is that I’ve been so swamped with work thanks to the great folks from Agile Reloaded that I didn’t have time or the need to flex my salesman muscles and get my own clients.

So sales and marketing are not my strongest suit. It’s not that I don’t know what could I do about it, I know the drills.

I hate pigeon-holing myself.
I hate the concept of having a “personal brand”.
I hate writing “to convert” using SEO principles.
I hate inventing new frameworks just to justify my competence.

As I mention earlier, my strategy on most things I don’t like doing is either:

  1. Be really good at something you hate doing so you get it out of the door as efficiently as possible, or;
  2. Create a strategy to systematically avoid doing what I don’t like doing (that how I ended up in consulting)

So I’m still searching a way to make point 2. happen, a strategy that doesn’t involved me becoming a “personal brand” or “writing SEO-friendly articles”.

I tried being part of communities of practice, interests groups or professional networks but again: when I’m into those communities, I participate as a human being, not as a salesman of myself.

I’m in love with the idea of packaging my services, or part of them, as if they were products.

But to do so I need to put more structured contents out there: I just have to write more, and then better. 

I’m learning how to design self-service, self-paced email-based courses.

I would like to teach in cohort-based classes.

I don’t think I’ll write a book.

And don’t wait for my very own organizational framework.


I, again, don’t have a plan or specific goals in mind.

But I have a clearer idea of what I want to do more of and less of compared to what I did during these past five years.

Less of

  • Agile for the sake of Agile: I think Agile has been ruined by consulting. We cannot go back. Lately I’m spending more time eradicating myths about Agile than to actually helping teams and companies to be more agile. I’m tired. It’s a losing battle.
  • Big companies: as much they provided a valuable training ground for me, my interests are shifting towards areas that right now are not “trendy” for big companies. I will continue to work with them, because there is still a lot to learn for me, but in order to evolve as a professional I think I have to find new training grounds in smaller companies.
  • Industrialized frameworks: it is closely related to the previous two point. It is undeniable that organizational framework and models are helpful. It is undeniable, that, as a consultant, being known as someone who’s knowledgeable in those frameworks is a commercial opportunity and advantage. But really, you are just selling someone else’s tool, it disheartening.
  • One-man band consulting: I see the independent consulting trends out there. I see the template for being a one-man band consultant. I don’t think it’s sustainable. I don’t think I would enjoy that. Ultimately, I don’t think I need to go that way.
  • Following the trends: I’m starting to see the contours of the shape of what a “post-Agile” consulting could look like. I’m not sure I want to take part of it. On one side I don’t like it because it’s a gamble, and as much as I can handle professional uncertainty, I don’t like to gamble.On the other side, it’s because I think that what you have to know, the tools, the practices, it’s already there, and has been there for a long, long time. We don’t need “new” stuff.

More of

  • Self-coaching: I believe in the ability of individuals and teams to self-coach and improve on their own. I want people to be able to come up with their own solutions, with as little dependence possibile from me. If I learned coaching and facilitation practices in a short period of time, you can too.
  • Smaller companies: as much as there are drawbacks in working with bigger companies, there are too for smaller one. But, having worked in smaller companies as an employee and with them as a consultant, it’s easier to get things done in a smaller company. It’s also easier, as a consultant, to be kicked out of the door. It’s fair game, and I’m up for it.
  • Smaller groups: I think that thinking that you can coach a 10-people team or an entire organization it’s a bit delusional. I don’t think even the best coaches can influence more than 3-4 people at a time. Especially while working remotely. I think that downsizing the scope and impact of coaching is the way to go.
  • Project management: I realized that project management is still one of the weakest areas for companies big and small. If you don’t understand project management, if you never experienced what does it mean to manage a project, it’s gonna be really hard for you to understand the benefit of Agile. So hear me out: “regular” project management is still cool, valuable and necessary.
  • Networked consulting: this is a counter to the abovementioned “avoiding one-man band consulting” point. I would really like to lower the “salesman pressure” that I feel by working with groups of other consultants with complementary skills that can pull me into new projects.
  • Projects: This is related to the networked consulting point above. I think that a lot of consulting in my line of work looks like an open-ended relationship, especially while working with bigger companies. I really want shrink down the window to three months and have shorter feedback loops with the companies I work with.
  • Remote: when the pandemic hit, I truly thought I had to change job (again!). I didn’t think it was possible doing remotely such relational, “in-person” activities such as coaching and facilitation. It is possible, although it required and is requiring a huge adaptation from everybody. But I think it’s time to be deliberate and explicit in considering remote as a default work setting.

The dark sides.

Fear of not being healthy: while physically I never had a problem so far, I know the dangers of not being mentally healthy. And the lifestyle of freelance consultant takes a huge toll on you mental health. It’s not an overstatement to say that the most important part of my job is taking care of myself.

I’m also scared as hell of not reaching age 60, since my father passed away at 58. When you are pushing 40 and you face you life as if you might already be at two-thirds of it, you outlook on life and work, trust me, it’s really different.

Fear of not being able to do anything of what you aspired to: things take a lot of time. There are ups and downs. I have a lot of things that I wanted to do, but I didn’t yet. I see them as failures. I shouldn’t. I realized that I’m always going to have a lot more ideas than time and energy to bring them to life. I have to live with that.

Fear of not making enough, or losing, money: every step out of the path you created, you are going to feel it financially, even hypothetically. If I say “no” to that project, I will probably earn 15% less this year. If I say I don’t care about Agile anymore, nobody will want to work with me. If I work with smaller clients, they might not pay me in time (or ever).

Fear of having to quit consulting and go back to a company: I enjoy consulting. My place is outside a company. I wish I knew it sooner. My consulting colleagues say “You’ve always been a consultant”. A few years ago, I would have been offended by such a claim. Now I wear it as a badge of honor.

Those fears don’t keep me up at night anymore, but they’re always present.

Know your demons, invite them for a coffee, have a chat with them.

That’s it, then, for now.

I have a feeling that the next five years will be even more interesting and wild than the previous fives.

If you wanna reach out to me and join me in the journey, write me at, or comment here below.

For the LinkedIn-inclined, you can find me here.