What I've Learned About Money Since My Own Great Resignation

What I’ve learned about money two years after my own great resignation:

Remember the carefree days of December 2019? That was when I parted from my 15 year corporate career, feeling financially confident and ready to jump into a new phase of my life. Little did I know that I would be walking straight into a global pandemic, a stock market crash, and a more uncertain world than I could ever have imagined. 

Since then, I’ve had numerous conversations with clients about second careers, sabbaticals, and downshifts. The pandemic has pushed us to rethink how we want to work and live, and some of us are ready to make career changes in order to prioritize purpose, flexibility and balance. 

Still, choosing to leave behind the security of a well-paying job – even for the best of reasons – can trigger all kinds of self-doubt and keep-you-up-at-night anxiety (I speak from experience). 

Here are my biggest learnings about money since my own great resignation:


1. There isn’t enough money in the world that can insulate you from the anxiety of uncertainty – so just embrace the uncertainty.

I stayed at the same company for 15 years, so I’m hardly the type of person who makes big career changes on a whim. I can’t tell you how many financial projections I ran before I felt comfortable with saying goodbye to a guaranteed paycheck. So when I made my jump, I did so with the safety net of a nest egg and a financial plan.

This is why I got into financial planning. Because if you’re like me, then anxiety about running out of money and ending up a penniless old woman is a huge reason why you don’t try for more. But with a financial safety net, you can jump more boldly.

That said, there is no amount of money that will protect you from the uncertainty that is inherent to life. COVID-19 made sure we all got that lesson. 

The truth is – no matter how many Monte Carlo simulations you run, the uncertainty isn’t going away. There is a non-zero chance that I could run out of money and end up a penniless old woman. But on the flip side, I also know there is an absolutely 100% chance that I will run out of time on this earth to do all the things that I want to. 

So when I get scared, I take a breath, embrace the uncertainty, and go on.


2. Shifting from accumulating wealth to living on your wealth is scary – but you get used to it.

As a society, we have this linear view of how our wealth should grow. We spend decades accumulating wealth (reaching the height of our earnings in our 40s, which unfortunately is also the age when many of us are raising our families). Then at some arbitrary time in our 60s (or 50s, if you’re lucky), we decide it’s okay to start drawing from our savings to fund our living expenses. We call this “retirement.” 

But choosing your own adventure in life means diverging from this path. And despite all the confidence I had in our financial plan, it still felt uncomfortable to see more subtractions than additions in our bank account. For the first six months post-corporate, I seriously considered applying for jobs (or, much to her chagrin, sending my spouse back to work). 

To combat the mental ping-pong, I set a deadline for myself. If after two years, I still couldn’t get comfortable with our new financial profile, I’d change course. The thing is – you need time to change and shed the mindset of your “old self.” And with each passing month, I did get more comfortable. 

A  friend who had early retired from a corporate career in his mid-30s told me that he too had counted his pennies in the first few years. But over time, his money fears abated. In fact, the last time I met him was at a fancy country club where he was a member, so clearly his spending attitudes had evolved. 

I also saw our new life begin to take shape – free time to spend with the kids and take care of my own wellness, launching our charity bike ride passion project, building a business that I care about. 

Drawing down from your savings to fund what you want in life can feel scary. But isn’t that the point of having money?


3. Not managing your spending is a problem. But feeling guilty about spending is also a problem.

Regardless of how much money you earn, the math says that you’ve got to live below your means in order to build wealth. Getting intentional around your spending is paramount if you want to achieve financial independence. This is why even though it isn’t sexy, I spend a lot of time with clients talking about expenses. 

It’s important to call out that being intentional is not the same as living under constraint. My perspective about budgeting is that it’s not about minimizing your spend, it’s about maximizing your joy – both now and in the future. 

My spouse and I take this very seriously. We meet monthly on our spending plan and have spending records going back a decade. Our intentionality with how we spend our money has been crucial for our financial successes. 

But there is a negative side effect – we sometimes feel guilty about spending. A lovely date night can end on a sour note when we see the bill and consider whether there should have been a better use for that money. 

As part of my financial life planning work with clients, I’ll ask the question: “Is there anything you’d regret if you were to die in the next 24 hours?” When my spouse posed this question to me, I jokingly answered: “I’d regret that I never blew all our money!” 

The thing is, I can’t even name anything specific that I’d want to blow my money on (okay maybe I’d upgrade to flying first-class, though the kids can stay behind in coach). What’s really behind that statement is my desire to spend freely – to live in the security that I already have enough relative to my needs and wants. 

That’s when I realized that I can already live this way today. I trust my internal compass enough to know that I won’t spend recklessly on stuff that doesn’t fit my values. I’ve done it before, and ultimately it doesn’t feel good. 

This month, I hired a meditation coach to start working with me one-on-one. On a more superficial note, in the same week I also spent a big chunk of change on fancy athleisure clothes. I felt my scarcity-minded self creeping up with both purchases (“that’s so frivolous!”). But both also make me feel good – plus I swear I can do heavier squats when I’m wearing those leggings.

I don’t need to wait for a 24-hour death sentence to start spending freely on stuff I care about.  I can choose that freedom now.


4. The highest form of wealth is freedom over your time and your destiny.

Financial writer Morgan Housel said: “Money’s greatest intrinsic value – and this can’t be overstated – is its ability to give you control over your time…The ability to do what you want, when you want, with who you want, for as long as you want, pays the highest dividend that exists in finance.”

I have freedom over my schedule, where I live, what I do, and how I build my business. 

One of the things I cherish most about this freedom is that whenever I get excited about something – a new hobby I want to try, an event I want to attend, or a project I want to start – I can just go out and do it. No more waiting for weekends or those precious few weeks of vacation each year. 

This is how my interest in finding more financial freedom for myself turned into informal coaching for friends, which then evolved into a full-fledged comprehensive financial planning practice. 

I’m grateful for this freedom to choose. In this tenuous world, Lisa and I recognize that we are amongst the privileged who can consider prioritizing purpose over paycheck. But my guess is that you could possibly as well. And I believe the world would be a better place if more of us were able to align our time and energy on the things that are most important to us. 


We specialize in life-centered financial planning for LGBTQ and other modern families who want the freedom to choose their own adventure. Like ourselves, many of our clients come from careers in tech and public service. Schedule a free money strategy session with me here