Unlocking Success: How 100€/Session On Coaching Changed My Career (And My Life)

A Startupper's Life - By Leo
Management Matters
Published in
4 min readJan 2, 2024
Photo by Jamie Street on Unsplash

“I don’t know. I don’t really know”

“You sure?”

…silence…

“Well, actually there’s something I could do…”

That’s when everything changed.

Let’s rewind.

Five years of hustling and trying to prove your worth to the company can be challenging. Proving yourself you are worth it, that’s a whole different game.

I had been working for the same startup tirelessly aiming at the big role, visibility, equity plan. My vision was clear and my actions were properly oriented.

I won’t lie: it did work.

It took me 4 months to move from Intern to Analyst.

It took me 1 year to move from Analyst to Manager.

It took me 1 year to move from Manager to Head of the department

Disney movie, isn’t it?

The brave character that, despite facing all possible adversities, achieves the dream by never giving up.

Soft music in the background. End of the movie…

…unless you remember that life plays its cards differently.

Having climbed the first steps of the ladder does not imply that you’ll keep on doing so.

I wish I knew it by then.

The company changed the org chart after thoughtfully planning the best strategy to achieve the only target that really matters: profitability.

That very change led to re-organizing all the existing functions, reallocating roles and hiring more experienced resources.

Bold move, sure, but you get used to that in the startup scene.

I quickly went from reporting directly to the COO and leading my team independently to having to follow another manager’s directions and reducing my span of control.

That’s when I happened.

All the self-doubts deeply hidden in the back of my head escaped their gates.

I started questioning my work, my decisions and, above all, my self-worth.

Because that’s what happens when you work 12 hours/day for years: you start looking at yourself through the lenses of your job.

You do fine? Life’s great

You do poorly? You’re sh*t

Those thoughts hit me hard.

I thought about quitting my job and taking a year off, exploring new paths, living new and refreshing experiences.

I didn’t (thankfully).

Sharing my self-inflicted pain with my family helped me regain control of my distorted stream of consciousness.

Reassuring voices, however, didn’t do the whole work. As unexpected as all the best bits of advice can be, my Mum told me how a coach helped her build a new perspective.

I’ll be honest here: I love my mum but “what the hell the she know about career issues? (She’s always been self-employed)

Well, as every child should know, mums know it all. Full Stop.

It took me a while to take the first step but, once I made it, everything changed.

That very conversation at the top pushed me to look for things that I didn’t want to see before.

Because that’s the truth.

We always know where we should be looking at.

Not doing is a different thing.

Results are great, but sharing the process is what really matters.

Before making the decision to invest in a coach, I ran simple analysis based on my work-related mental framework:

  • ROI: assuming that the process worked, I would have achieved clarity on what I wanted and started acting upon it. The ROI on solving a nonmonetary problem might be hard to calculate but, if you look at your mental health, I would be everyone would associate to it a great value. On the other hand, I would have “just” wasted of couple hundred €.
  • Compound Interest: as every “Finance For Dummies” book would teach you, the earlier you start investing and cumulating returns, the greater the impact of any additional year. That’s the same for self-growth, or at least that’s how I looked at things. By assuming the earlier the better, I assumed that acting fast would have allowed me to reap greater returns in the long term.

Luckily, it proved to be the right thought process.

My coach’s support came through all those questions that I did not want to ask myself:

  • What’s under my control that I can change?
  • What would my ideal situation be like?
  • How important and urgent is this situation for you?
  • …many many other (but that’s a different story to publish)

But let’s cut the process I here, I promised to share the results.

I didn’t forget:

  • I changed country.
  • I changed job.
  • I changed myself.

and that’s all I wanted.

Focus on the question, let the answer come.

PS

Coaching evolved into something more and after 9 months of courses I certified as a professional one.

Yep, life is (wonderfully) strange.

PPS

Thanks Mum!

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A Startupper's Life - By Leo
Management Matters

Hidden under a pen name, exposed through my stories | I write to share hard-earned lessons in business and life, guiding others to success without the pitfalls.