Why “I Could Make It All Back” Misses the Point

There’s a specific kind of discouragement that comes from hearing successful people say:

“If I lost everything tomorrow, I could make it all back.”

Not because it’s wrong.

But because if you’re early in your career — or starting from scratch — it can quietly translate to something else entirely:

I don’t have what they have. So what chance do I really have?

What’s usually missing from that statement isn’t skill or mindset.
It’s context.

Most people who could “make it all back” already built something more valuable than money: a network of trust, relationships, and people willing to bet on them.

There’s a huge difference between having little money with a strong network and having little money without one.

And if you’re in the second group, that realization can feel discouraging at first.

But it can also be freeing.

Because it means money isn’t the only advantage that matters.

Being Underestimated Isn’t Personal, It’s Familiarity

When I first started tutoring, nobody in my personal life really encouraged me to do it.

Not in an active, discouraging way.
No one told me not to try.

But I also don’t think anyone genuinely believed it would turn into anything.

At the time, I didn’t have a degree in teaching. Tutoring wasn’t a path people around me recognized as legitimate or sustainable.

What I learned from that experience is something I still come back to:

People aren’t skeptical because they see your limits.
They’re skeptical because what you’re doing is unfamiliar to them.

Most people feel safer around paths they’ve already seen work, careers they understand, credentials they recognize, trajectories they can explain to someone else.

When you choose something outside that frame, concern often shows up as quiet doubt.

A Note to My Early-Career Self

The people around you aren’t doubting you because you’re incapable. They’re uneasy because what you’re doing doesn’t fit into a box they recognize yet. That discomfort isn’t a signal to stop: it’s a signal that you’re early. You don’t need permission. You don’t need proof. You need reps, patience, and the courage to keep helping people before the results are obvious.

Generosity Before Proof

Instead of trying to convince anyone, I focused on something simpler.

I focused on helping students learn and on getting better at teaching.

Early on, I charged very little. Not because I didn’t value myself, but because I saw it as an investment: in my skills, in real outcomes, and in trust.

At the time, I didn’t think of it as generosity.
I thought of it as learning in public.

Over time, that effort started turning into trust.
That trust turned into referrals.
Those referrals turned into opportunities.

Eventually, yes it turned into money.

But the money came after the value.

Money Isn’t the Leverage People Think It Is

That experience reshaped how I think about careers.

Money isn’t the real leverage people think it is.

Networks are.

And networks aren’t built by impressive people. They’re built by people who are useful, generous, and consistent especially when they don’t have much to give yet.

That generosity doesn’t have to be dramatic. It can be:

• Showing up and listening carefully

• Following up when most people don’t

• Helping without immediately asking for something back

These actions don’t feel powerful in the moment.

But they compound.

What You Still Have When You’re Broke

If you’re early in your career, no one expects you to have money.

But people do notice effort.
They notice curiosity.
They notice follow-through.

If you’re broke, it doesn’t mean you have nothing.

You still have time.
You still have attention.
You still have the ability to help.

Those are the raw materials of a network.

And over time, wealth follows value not the other way around.