One Question That Saved Us Years On Our FIRE Journey

I juggle a lot of different projects – writing, teaching, consulting, speaking — but the one thing they all have in common is being advice-related.

Earlier this year, I did a talk on work/life balance in Philadelphia, and an attendee asked for advice on what to do about perfectionism. I also get questions on what to invest in (is Costa Rica a good market for real estate?), what industries are hiring, or some variation on what is the best next step.

I love questions – both questions I get and the ones I ask. The questions I get inspire many of my blog posts, like when Damn Millennial asked about why we chose a cash-out refinance over a HELOC. The questions I ask inspire new ideas and point me in different directions.

One question in particular saved us years on our FIRE journey, and enabled Scott to leave his desk job for a more flexible lifestyle sooner than we expected.

Replace ‘What’ with ‘How’

How is the magical question behind many of our big life pivots and the one that propelled us into FIRE. Rather than thinking up specific tactics – what is the best investment or next move – you focus on the end goal you want (e.g., the FIRE lifestyle) and then explore, even if you initially have no idea, how you might get that.

What-focused thinking is like picking a specific financial independence number. What amount of passive income do we need to be financial independent from a job? What investments should we make to maintain this income? What risk management moves should we make to preserve our stash? What budget do we need to stick to in order to stay within a safe spending zone? You plan around these questions and get to the FIRE lifestyle with your plans.

Financial Independence (FI) is a moving target

The problem with What-focused thinking is that circumstances change and tactics may need to adapt beyond your initial idea. I always had an FI number in mind. My first job was in banking, and there is a lot of chatter in that industry about the number you need to be financially independent (aka – the F.U. number in banking circles).

However, when we finally approached our pre-designated FI number, the math went out the window and my risk-averse tendencies took over. This can’t be enough. College run hundreds of thousands of dollars. New York City is expensive. There’s no way this number can be right.

I wasn’t going to feel financially independent based on a number. I had to get there based on knowing I could adapt regardless of where the number may rise or fall. There would be many unknowns.

But I listed out what we did know and then asked How:

• We’re too young to accurately guess our life expectancy so we need to generate enough income without touching the principal.
• We want to travel so our income has to be location independent.
• Our kids want to stay in New York City but we want to move.
• How do we do these things?

Focusing on How changed our mindset from Knowing to Learning, and from Someday to Now

Since we couldn’t rely on a single magic number or any one foolproof plan, we had to get comfortable with just learning as we go, rather than knowing everything before we started.

This also meant that there wasn’t any real benefit to putting off a purely flexible lifestyle any longer. I had already left my office job years ago, but Scott was still tethered to the typical workweek and limited weeks of annual vacation.

How could we live a FIRE lifestyle now, not some other time?

This set in motion many new things in just the last few years – setting up lower cost long-term hubs in Jacksonville and Costa Rica, buying an apartment in a completely different neighborhood of New York City from where we lived for decades, starting this blog, and experimenting with other new projects.

In making these moves, Scott was able to leave his job years ahead of our theoretical schedule, enabling us to jump-start our travel, and giving us the flexibility to start a FIRE lifestyle now.

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How about you? Is there something you have been wanting to do? How can you do it now?