The Tension Between Freedom and Security

By Liesa Witt · Published 2026-06-12 · Updated 2026-09-07

For the past three years, I’ve been building a life around freedom: running my own business, choosing how I spend my time, and creating work on my own terms. What I didn’t fully anticipate was the constant tension between freedom and security.

One of the biggest internal battles I currently face is this:

How do you create freedom without sacrificing all sense of security?

I’m now in my third year living and working in NYC on an E-2 Visa.

Working for myself gave me things I deeply value:

autonomy, flexibility, creativity, independence, ownership over my time.

But it also introduced a level of uncertainty I had never experienced before.

Because suddenly your life becomes connected to questions like:

And the honest answer?

Sometimes the answer feels terrifyingly simple:

You would be screwed.

That realization changes how you think.

At one point, I started calculating everything through the lens of time and survival.

If I had 10 months without stable income:

Could I realistically design, validate, build, launch, market, and monetize a product before the money ran out?

Maybe.

But bootstrapping software while surviving in NYC is a very different reality than the motivational content people post online.

I had never built software before. Luckily vibe coding makes things a whole ot easier these days. Nevertheless, that is only half of it.

And suddenly I am trying to solve questions founders with funding, teams, and technical backgrounds struggle with everyday.

That was the big pink elephant in the room.

Not ambition. Not ideas. Execution under pressure and not having a partner to keep you sane at times.

When I say partner I am mainly referring to a business partner. Nevertheless, as a woman in her end thirties I am also faced with the challenge of finding my matching puzzle piece for a romantic partner to build a life together. This however, will be a topic for a later point in time.