Nobody likes to talk about money, but let's do it anyway, because for anyone who considers the leap to becoming a digital nomad, it's generally the first consideration.
Everyone's financial situation is different, and everyone who lives like I am got here via a different route. Some had wealthy families (how nice!), and some busted ass for a long time to be able to do it. I won't say "anyone can do it" because that's a lie. The truth is, it's a privilege to be able to quit a stable job and go on the road. But in case it helps anyone who's considering it, here's how I did it.
I did a boring, standard climb up the university administration ladder for over a decade. I started out teaching English as an adjunct (and what an abusive life that is), then I took a year long appointment running a writing center to cover someone's maternity leave. That opened the admin door, which got me a coordinator job in a town I'd never heard of and moved me across the country. I climbed the ladder for 10 years because that's what you're supposed to do, right? And then I realized I wasn't happy, and I'd become place-bound in a place that didn't feel like home. If I continued on my current path, I knew, I would just hang around waiting for a pension, then waiting for retirement (if I didn't die of stress first), and I'd never live the way I wanted.
The most stressful part of quitting a full-time, salaried job to start your own business or freelance is definitely creating the monetary cushion that allows you to do it. No one wants to get into a situation where they're living in a new city without owning a home and with bills to pay, and suddenly work dries up. And work can in theory dry up at any time. Then again, those full-time jobs that seem 'stable' can also be gone tomorrow too, so you pick your poison.
As an anxiety person, thinking about the financials of making a huge career change was stressful. I grew up in a household where money was always an issue. My parents lost my childhood home and filed bankruptcy. Then they filed bankruptcy again after starting a small business that didn't pan out. Seeing how this ruined their credit and made buying anything difficult for them spooked me, and money has made me nervous ever since. Not having money makes me nervous. Having money also makes me nervous because I feel like I have to spend it right away or it will simply vanish. It's an irrational mindset, but one that lots of people who grew up in financially unstable situations experience. It also took me a long time to understand that the monetary priorities of people with and without are different. So when I got promoted at my job and started making a middle-income salary, I felt like I couldn't move a muscle or I'd risk poverty.
I did, however, make a couple moves that helped set me up to be able to do what I'm doing now, though I didn't know it at the time. First, I got my PhD, but I didn't pay much for it. I only got it because the university I worked for would cover 80% of the tuition, and it's a cheap university to start. I took out just a small amount in loans. Had I needed to pay all of it myself, there's no chance I would have done it. Completing the degree got me promoted, which allowed me to buy a house. (Education truly is the key to upward mobility.)
Buying a house is something I never thought I'd be able to do, but it turned out to be the thing that propelled me to quitting my job and going on the road. I bought a house that was nowhere near those ranges the bank says you should be in based on income. It listed for 85k. According to the bank, I should have been looking at 125-140k houses. I'm very glad I didn't. So I bought my modest, cute house and did a 15 year loan so I'd pay it down faster. (Having a lot of debt on top of student loan debt from my undergrad/MA was anxiety-inducing!) I had to put 20k into the house, which needed a basement waterproofing and a new roof. That meant a home equity line and a loan. Damn. This seemed to be turning into a financial black hole. Still, I plugged away at the mortage and over-paid those loans every month.
And when the housing market got wild during Covid, and my job became unbearably stressful and no longer worth the salary, I decided to sell. After all, if I was going to quit my job, (and I knew I had to), there was no need to stay in Terre Haute, Indiana, a town that I'd moved to solely for work.
I didn't know how fast I would sell, or how much I would get, but I knew that when I moved, I wanted a good solid financial cushion, so I started picking up grant work on the side and quickly found that that would easily sustain me. I added about $4000 a month to my income doing that on the side (the same amount I actually saw in take-home pay from the university) and stopped spending aside from necessities. That cushion grew fast.
Then, within a few days of listing, my house sold for the asking price, which was way above what I bought it for. (Thanks, ridiculous market!) It was enough to pay off the home repair loans and my used car and give me enough to live for a year and a half even with no additional income. Getting that large check at closing about gave me heart palpitations, so I threw all the extra after paying stuff off into a money market account - a thing I didn't know existed until I researched savings accounts. There it will be touched only in an emergency. If I have no emergencies, one day it may become a healthy down payment on another home. But that would be far in the future.
And that's what allowed me to make the move - having a year and a half's worth of money from selling my home. And I'm lucky enough that grant work keeps coming, so I'm able to add to that cushion a little at a time.
I wish I could say "see, it's easy! Anyone can do it!" But that's not the case. I'm here doing what I'm doing by a combination of luck (like that sweet seller's market), education, and being terrified about money, which caused me to buy a house well below my price range. But I will say, if you know you want to make a move, look for those windows. Keep an eye on the housing market if you own. Develop a side hustle and keep close track of how many hours you COULD be working it a week. That will tell you if it could be a full-time income. Budget the shit out of everything. (I'll do another post on budgeting for a nomadic life later.) Wait. Be patient. Do it when you're financially ready. For me, that was a 10 year wait.