Block Woman and many other Block People of different sizes and colors.

Conversations about life with 15 people over just two days is a fascinating, if tiring, experiment.

And one I poorly time-managed my way into in December, during my annual pilgrimage (interrupted by the pandemic for a few years) to the Bay Area to catch up with family, friends, and clients. I met with 15 clients over just two days. 

These were “So, tell me about your life” conversations, not “Let’s talk about your money” conversations. And yes, there was a lot of coffee and meals involved. (Side note: What is up with San Francisco’s obsession with sour coffee?)

Having so many conversations in such a short time made it easy to spot common themes in people’s life experiences and perspectives. I mentioned this observation to a few clients, my teammates, and even the friend I was staying with. They all surprised me by asking the same thing immediately in response: So what were the common themes?

I assume not many people have a job where you get to have meaningful conversations so often with so many people. My job as a financial life planner gives me that rare—and beautiful—opportunity.

I wanted to share my reflections with you in the hope that you’ll find comfort or excitement in the company.

So Much is Determined by Luck. And That’s So Hard to Accept.

We work with a lot of clients who went through the Airbnb IPO. Some of our clients got millions of dollars out of it. Some of our clients got a few hundred thousand dollars.

I had breakfast with a client in the latter camp (and a frangipane croissant…yum). 

Obviously, few of us can comfortably complain about “only” a few hundred thousand dollars. But if you’re surrounded by people and stories of people who received millions and went right out and bought an expensive home or became financially independent and quit their jobs, the (inevitable) comparison game is not your friend.

Why did this client get “only” a few hundred thousand dollars, instead of a few million? Because she joined Airbnb just a couple years before they went public and therefore didn’t accumulate as much company stock as other longer-term employees did. In other words, luck. 

Those colleagues of hers were simply lucky enough to join Airbnb years before it went public. 

They were lucky enough that it in fact did eventually go public. 

They were lucky that it went public successfully

There are lots of ways in which luck has a tremendous influence on your finances:

  • When you choose to sell company stock
  • What happens to the real estate market after you buy your home…or while you’re waiting
  • When you buy a cryptocurrency (shitcoin or otherwise) and, even more importantly, when you sell it

So much—I’d wager, most stuff—is out of our control. Luck is the dominant factor.

In my opinion, the only solution is not to magically find better luck or think you can work hard enough to override luck or lament being not smart enough to override luck. 

The solution is to focus on who you are, what you need, now and in the future, as best you can.

It is to make decisions based on your knowledge of you. Are you comfortable taking risks? Do you really want to own a home now? Is it the right time in your life (not in the real estate market cycle)? Do you need money from your company stock in order to securely fund a 6-month sabbatical? And so on.

Planning in an Uncertain World 

I met with a client over (yet another) frangipane croissant and an oat-milk latte. (Okay, second complaint about coffee in San Francisco: I couldn’t find soy milk anywhere! Seriously? Is soy milk “so 2009”?)

This client has one, young child and is pregnant with her second. She mentioned that going into baby #1, she wanted to have a plan for after the baby arrived. What would her job situation look like? When would she return to work? How would this, that, or the other “work” after she gave birth?

And then, as any one who has a child knows, her new baby introduced her into a world that she could have never predicted or understood.  

Now, going into having her second child, she was pretty chill about planning for after the baby arrives. The arrival of baby #1 had taught her that planning for utter uncertainty/unknowability is kind of a waste. (She is also an above-average self-aware person.) 

This led into a discussion of planning for goals (which, for me personally and for many people I know, isn’t an idea that really resonates) versus planning for intentions (this framing works better for me). For this client, she focused on neither of those things in her planning. Instead in all of her planning, she focused on “expanding optionality.”

In a world where we don’t know and can’t know what will happen in the future, making plans that “expand optionality” sounds like an amazing (and healthy and smart) approach. 

In fact, in my world of financial planning, I can easily see how our approach helps people accomplish just that. 

We divide financial planning into risk management and opportunity planning. 

  • Risk management includes things like building up a cash cushion, getting the proper insurance coverage, etc. 
  • Opportunity planning could, for example, include saving up even more cash in order to take a break from your job, in order to figure out what you want the next step in your career to be. 

In all those cases, those financial acts increase your optionality, or, as I have usually called it, “flexibility.”

What Makes You Resilient?

The last few years have reinforced our need to build our resilience. Because, evidently, the hits just don’t stop coming.

I have found in my work with clients a tendency to conflate “more money” with “resilience.” 

And certainly, money is a good resource for making you resilient. Money can buy you time, access to help, and safety.

But it’s by far not the only resource you have that makes you resilient. 

I hypothesize that the ambient culture in the Bay Area (maybe especially in the tech community there) puts wealth on such a pedestal that it causes us to forget the other resources we have to make our lives both fulfilling and resilient. 

I was reminded of this by a client (over a turmeric tea), as they were telling me about their boyfriend, who was not in the tech industry. The boyfriend makes far less money than my client, has a very different perspective on technology and life and money, and lives a meaningful life.

What other resources do you have? What other sources of resilience do you have? 

  • Personal relationships
  • Professional relationships
  • Skills
  • Experience
  • Grit
  • Native intelligence
  • Government and religious and other community support networks

The Primacy of Self-Work

Self-work is so important to this financial work…and everything else, really. 

I sense this is especially true in the Bay Area, where wealth and professional success (i.e., external manifestations of success) are so visible, so publicized, so put on a platform for reverence. 

But not only is the story behind the money and success never fully known, none of that has any relation to who you are, what you truly want, what your values are.

If you don’t make a regular practice of continuing to clarify, reaffirm, and discover anew your true self, I fear it is far too easy to fall prey to all those external measures of Right Spending and Right Career Choices and Right Wealth and Right Doing and Being. 

I imagine there are lots of ways to have such a practice: conversations with true friends, a therapist, meditation, walks in the park, volunteering, etc. 

I’m not a therapist by any means. Thankfully, many of our clients (and I!) work with therapists—or even if they don’t, are similarly inclined—and so are willing to engage in the self-work part of financial planning.

Being a financial planner means I get plenty of exposure to people’s struggles (my own included) to make financial decisions that feel “right.” In my experience, the decisions that are the right-est are the ones that help people build better relationships, build a life that feels meaningful, and get healthier. 

Figuring out which relationships matter, what provides meaning in your life, and what health looks and feels like…that requires looking in, not out.

All of this emphasized in a conversation with a particularly introspective client, over a delicious soyrizo burrito bowl at The Little Chihuahua. (I was surprised by how hard it was to find enough vegetables to eat as I was eating my way through San Francisco! This bowl was heaven sent.)

Leaving Tech for Another Career Is Doable. And Pretty Great from the Looks of It.

Leaving your tech job and pursuing something entirely different is a fantasy for many of our clients.

We’ve had several clients do this. I got to speak to two of them—over a mushroom empanada and grilled romaine hearts, respectively—just in this one visit. 

One client is a 30-ish-year-old woman. She was laid off earlier this year. From a job she hated, but still, getting laid off sucks. Thankfully (!!!) she had participated to the max in the most recent tender offer her large, private employer had offered, so she had not just lots of future fantasy money (in the form of company stock), but also lots of cold hard cash she could use now to ease her transition into her next career. 

This client is now working in event planning. She’s flexing her creative muscles. The new job has both desk work and physical work. She’s not making nearly as much money, and perhaps she’ll eventually have to make more, but for now she has plenty of money to give herself the time to see how it unfolds. 

Her happiness and interest in this new job are a far cry from the self-described “death rattle” of the last few months at her old job.

The other client is a 50-ish-year-old woman. She had spent decades in tech. She quit her job, voluntarily leaving a high salary and lots of public-company RSUs on the table. She’s going back to school to become a middle-school teacher. 

Just as with the first client, this client’s current financial situation isn’t sustainable forever, but she and her husband had built such financial strength over the years that they have plenty of time to see how her new career unfolds, and to adjust as needed.

This client is similarly excited about her new career outlook, in a way that I hadn’t seen before.

Both of these clients, with their financial choices over the prior years and decades, had created for themselves that “optionality” mentioned above. And they’re both now happily, if still trepidatiously, taking advantage of that.

Cars Are the Best. 

This is not a phrase I ever imagined writing, just because of my personal values and preferences around cars and transportation. But I can’t deny the data.

And the data (all three pieces of it) say cars are great.

Three clients mentioned how great it has been to have a car while living in San Francisco. Two of them bought a car just in the last year or so.

Even more specifically: Subaru Crosstreks are the best. (Two clients within 24 hours mentioned this specific car. I had to smile.) Oh, and if you have one, keep in mind that there’s some after-market widget you can install that makes the auto shut-off less irritating.

2022 Was Hard for a Lot of People.

Even with the pandemic waning, there was still a lot of external shittiness in 2022. Death. Illness, for oneself and one’s loved ones. Layoffs. Breakups. Then of course the tech and stock and bond markets went down, as well as inflation up. 

There was also just a lot of bone deep exhaustion. Burnout. Depletion. 

I had one client (over a pork-and-jalapeno pupusa) tell me that she finally realized she was in “late-stage burnout.” And plenty of other clients had stories of a really challenging 2022. 

You know those apocryphal stories about a mother whose child gets trapped beneath a car? In a miraculous feat of adrenaline-fueled strength, she lifts the car up so her child can get to safety. Then she collapses into a broken heap on the ground.

I think 2020 and 2021 are the car, and we (all of us, not just parents) are the mothers who exerted Herculean strength to get through that crisis. 

When the pandemic crisis waned in 2022, we were safe(r) to collapse into a broken heap on the ground. Safe(r) to let all the emotional, psychic, and physical damage and pain from the previous two years surface. 

And it’s ugly. (Well, I can confidently speak for myself. It’s been ugly for me, for sure.) Before we can even think about “thriving” again, before we can think about returning to our pre-pandemic lives, we have to heal. We have to recover. And the start of that recovery has been b.u.m.p.y.

Though the conversations were intense and tightly packed, they were rich and rewarding. Also, I haven’t eaten so well in a long long time. 

We might have death, illness, layoffs, and a scary economy. But we also have persimmon carpaccio, flaky croissants, amazing green olives with what must have been orange zest, and homemade pappardelle.

I retroactively lift that glass of delicious champagne (thanks, foodie client couple!) to 2023.

Do you want to work with a financial planner who encourages you to do the hard work of examining all aspects of your life, not only your finances? Reach out and schedule a free consultation or send us an email.

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