Author: Sabrina Giacalone

A reflection on work, purpose, and the moment we decide what kind of life to teach our youth.

Today, my 15-year-old son told me he wants to get a job.

He is an artist and an animator. The kind of person who sees things before they exist.

When I asked him why he wanted a job, he gave an answer that felt both logical and deeply familiar: he wanted money so he could support himself and pay for the things he needs to become a better artist.

And that gave me pause.

Because beneath that answer was a lesson so many of us absorb early and rarely question:

Work first, so you can afford to become what you already are.

The more I sat with that, the more I realized this is not just a parenting question. It is a leadership question.

We often inherit a model of success that teaches people to separate survival from meaning. We normalize trading time, energy, and originality for the promise that one day, after enough proving, enough earning, enough exhaustion, we might finally have permission to invest in what we are actually gifted to do.

And then we wonder why so many people feel disengaged.

Why calendars are full, but people feel disconnected.

Why capable, creative individuals lose clarity, energy, and conviction over time.

I see versions of this everywhere, in workplaces, in culture, and if I am honest, in myself too.

Leadership is not only about driving outcomes. It is also about recognizing when a system is teaching people the wrong lesson.

In that moment with my son, I realized I had a choice. I could reinforce the default script, or I could challenge it.

So instead of telling him to get a conventional job first, I asked a different question:

What if your art is the thing that begins to support you?

What if he started offering commissions, building a portfolio through real collaboration, learning how to translate other people’s ideas into work that carries both skill and value?

That conversation was about more than money. It was about whether we teach people to delay their calling or develop it.

As leaders, parents, managers, and builders of culture, that question matters.

Because every system teaches.

Every norm shapes identity.

Every repeated message tells people something about what is practical, what is valuable, and what kind of life is available to them.

We do not just teach people how to work.

We teach them what kind of future they are allowed to imagine. Or better yet, that the future they imagine themselves is allowed.

And I think more of us need to stop and ask:

Are we helping people build lives that are sustainable, integrated, and meaningful?

Or are we simply preparing them to function inside systems that disconnect them from who they are?

That is not a small question.

It may be one of the most important leadership questions we can ask.

Read the full letter on my Substack: What I Told My Son Instead of “Get A Job”