Relationship with Money
A blog that knows money is more than numbers
206 | Counting Days
A change that helps you quit counting days is better than a raise.
Because counting the days until you can quit is the bouncer at the door turning meaning and purpose away so the need for "just a little more" can stay.
There's no question that a bonus or a raise, especially the first one, is one of the sweeter feelings in the world.
Validation. Affirmation. Freedom. Lots of feelings that add to the sweetness.
It’s so sweet, that our attention can't help but move to the next one.
One that is barely less sweet than the one before - the taste buds likely don't notice.
But over time, the sweet has a way of fading or even growing bitter...
Especially once it's nothing more than the scissors that cut another link off the retirement paper chain.
We'll never be able to measure it, but the downsides of counting days can't be offset by a raise.
204 | Relentless Pursuit
The ultimate career skills...
- Finding work that feels like play
- Knowing how to put it down
Because too many hours of your life are spent at work, and no one wishes they worked more once they're done.
Of course, work that feels like play doesn't fall in your lap.
But slowly making it feel like leisure begins to pull us in the right direction.
Even if it takes a couple decades or (gasp!) a dip in income, it runs circles around grinding it out until you're worn to a nub or obsolete.
It's hard to comprehend the shift that occurs.
Work that doesn't feel like "work" is one thing.
But the upside of something that's fun versus something that's tedious is 🚀.
The real risk is work that feels like play might be hard to put down.
And it's easy to blame a client or a boss or an inbox for why work owns your life.
But every field has someone who is exceptional without being consumed.
That's who we want to notice - not to uncover their 10-step process, but to appreciate the courage needed to draw hard lines along the way.
What's the secret to a good career?
Relentless pursuit of work that feels like play.
And relentless pursuit of how to put it down.
185 | Unlocking Golden Handcuffs
If you spend all your income, then those handcuffs are solid gold, and the key is going to be hard to find.
But if you've been able to spend less than you've made, the key is probably in your pocket.
Financially, the key isn't much more than building up some cash, and pursuing a level of income that comes close to covering your spending (no dramatic lifestyle cuts needed, but probably no big additions for a brief period too!).
A few break-even years never killed anyone, particularly when you move from something you've grown to hate into something that's closer to what you love.
Emotionally, it's going to be recalibrating to account balances that feel more like a glassy lake than an ocean that keeps delivering wave after wave of new funds with each payroll run.
And that's going to be the hard part - the feeling, not the funds - especially in a world that likes metrics and struggles with intangibles.
But if you cringe at the work you do.
Or the culture of your company is deteriorating.
Or your remote work arrangement has been pulled out from under you.
There's a pretty good chance that a few break-even years will do less harm than trying to gut it out with your hands behind your back.
159 | Two Questions about Life Insurance
Should you have life insurance?
If someone else's well-being depends on income that you generate, then probably yes.
If someone else would become responsible for debt that you owe, then probably a double yes.
If neither of these statements is true, then probably no.
Would I ever sell life insurance?
Absolutely not.
I don't want to be tied to the process of approving someone for life insurance nor do I want to be compensated for selling it.
Sometimes there are disappointing outcomes that occur in the approval process. If a line is going to be drawn in the sand, I plan to be on the same side as my client.
And you don't pay someone to place you into the correct life insurance product. Someone gets paid based on the life insurance product you select. It doesn't take a genius to realize that a life insurance product requiring less effort and/or more compensation is appealing for someone with a sales quota.
128 | A Spectrum of Sustainable Income
Income is any money coming into your household that is above and beyond what you have already saved or accumulated.
It's the purple bar.
For many, it has a way of tethering lifestyle to it in either direction. More income equals more spending. Less income equals less spending.
I think this is because there is something less psychologically taxing about using income for spending than there is dipping into what you have saved for spending.
Most folks are tempted to think it is a matter of maximizing income, but I'd challenge that it's more a matter of maximizing the sustainability of income.
Income that has no shelf life - no expiration date, no defined term, no day of reckoning on the horizon - takes personal financial freedom to a different level than any raise or signing bonus or new client can provide.
A dollar is a dollar no matter where it comes from. But the chances that additional dollars will continue showing up is how I'd measure sustainability.
Here's a rough spectrum of income sources (or purple bars!) from least sustainable to most sustainable...
Income from a gift - much like the $20 bill you find in your pocket, income from a gift is surprising, novel, and fun, but hard to depend on repeating forever.
Income from the sale of something - we're not talking about selling a service or inventory as part of a business model. We're talking about selling a business, a car, a property, a collectible, or anything else that you own that is valuable for a one-time profit. Sometimes the profit is enormous, but usually the number of things you can sell is finite.
Income from a gig - often it's the only way to get started in a new career or venture, but at least initially, it's as sustainable as your marketing efforts or your existing network allow it to be.
Income paid on an hourly basis - an upgrade from a gig, but there are a finite number of hours in the day. If your hourly rate is sufficient for your lifestyle, then move this further up the list. If you're unsure whether it is or not, then you're on a slippery slope of endlessly trading time for money.
Income from something you're dying to quit - at best this income is paying the bills, and at worst it's distorting your view towards work, money, time, and relationships. This one feels like a sneaky unsustainability that is often accommodated and ignored at the expense of almost everything else.
Income from a business that is no longer relevant or profitable - this one is a matter of time - how much longer until the oil well runs totally dry?
Rental income from a property you are managing into disrepair - this is the real estate version of the previous one. From an income perspective, this one is less about the current tenant and more about who's next when the current one inevitably leaves?
Income from a business that is not yet relevant or profitable - this one is a matter of time - how much longer until your patience, perseverance, or energy gives out?
Income from a physical activity - Just ask a 38-year-old professional athlete how sustainable they believe their salary to be.
Salary or fixed compensation from a specific role - more sustainable in the near term, less sustainable in the long term. When things hit the fan, management can't help but eliminate fixed costs. This one is as sustainable as your ability to add value for management.
Bonus, commission, or variable compensation from a specific role - less sustainable in the near term, more sustainable in the long term. Taking responsibility breeds sustainability and getting paid for production means you're responsible for what does or doesn't happen. This one is as sustainable as your ability to add value for clients.
Rental income from a property you are maintaining well - a waiting list is a sign of sustainability. If people are lining up to live there, that's a good sign. And it seems likely that people will always need a place to live.
Dividend income from an established business in which you are a key contributor - income that comes from the profits of a business directly to its owners. Often there is significant upside potential as a key man or woman, but the concentration risk of putting all effort and energy into one business has a way of undermining sustainability.
Income from something that you'd be willing to do for free - in terms of exchanging effort for income, it's hard to think of something more sustainable than transforming "effort" into "pleasure".
Dividend income from a business that does not require you for its operation - Of course, dividends are never guaranteed, but once you start receiving them from an ever-growing list of companies, you can begin depending on them in a different way.
Interest income - income that is required to be paid by a contract and ensures you're first in line to get paid if the business hits rough patch. The more of these arrangements, the merrier from a sustainability perspective. A healthy appreciation for inflation and possible loss of purchasing power is the only prerequisite with this income.
Pension income from a company - there's a reason you don't find many of these anymore, the sustainability was a holy grail for a former employee and an anchor around the neck for the business still trying to innovate and operate.
Social security benefits - it's hard to find something that can be sustained longer than an inflation-adjusted monthly payment from the government against whom all other creditworthiness is judged.
Of course, income is only part of the story - if you spend more than you make, then no level of income is sustainable.
But if you're moving up this spectrum, chances are you can depend on your purple bar to be around as far as you can see into the future.
100 | Good at Something I Hate
My mom will cringe when she reads that title and we try to correct our kids when they use that word, but I’m struggling to find a synonym right now.
Honestly, I strongly disliked my first professional role after college.
I enjoyed some of the people and am still grateful for those relationships. I learned valuable skills that I still use every day. I even feel pride when I tell people about my first job because of its prestige in the accounting world.
But working in cramped conference rooms until after midnight, documenting why some innocent A/P clerk kept a less-than-perfect paper trail, and missing out on plenty of evenings with my wife and friends is something that had a shelf life from the day I started.
But here is the irony - for as much as I disliked the role, I was pretty good at it. Not a Hall of Famer, but I certainly would’ve made the playoffs every year.
Pretty quickly the nagging question was, “If I’m good at this and I hate it, how good could I be doing something I love?”.
Of course, the opportunities for promotion were substantial. The income potential was seemingly infinite. The promises of paid sabbaticals were sexy on the surface. But I never envisioned myself climbing the ladder if I was grumbling and crying all the way to the top.
I worked my last day in that role in September 2013 - I don’t think it was the 13th but it would be cool if it was. I can still remember sitting across from the partner of our group in my last week as he said, “I think you’re making a big mistake.”
Depending on your definition of “mistake”, the jury may still be out on that one.
But today it is September 13, 2023 and this is Post 100. On January 1 of this year, I set a goal of 100 posts in 12 months.
I’m not claiming they are all good, but completing a 12-month goal in less than 9 months feels like something that happens when you love what you’re doing.
There’s still a long way to go, but that long runway would have made me throw up in September 2013, and now it gets me excited.
It feels like we’re starting to answer that nagging question instead of just wondering about it.
81 | One of My Biggest Fears
"I miss when I thought chasing dreams was
Holy magic behind curtains in a sacred place
Before it was managers and lawyers
Who colored up and cashed them out
For vacation homes in coastal states"From Heroes by Ben Rector
Yes, I had to look up the definition of "colored up" - in a game of poker exchanging many low-value chips (of one color) for fewer higher value chips (of a different color) while keeping the same overall value - but as soon as I did I had goosebumps.
I've never had the words, but this is the essence of an "anti-goal" that I have used throughout my entire career.
I've been afraid of managing and coloring up and cashing out - it's as if the very concept has been the opposite end of an invisible magnet repelling me away from some career paths and final destinations and pushing me in the general direction of others.
I've been scared of the way coloring up and cashing out would place the outcome ahead of the purpose.
I've been scared of the way it would slowly and quietly suck the life out of how I spend my days.
I've been scared of the way it would distance me from family, friends, and strangers alike.
I'm scared of the way it would sneakily place money and what it can buy above most things that are a lot harder to measure.
I'm scared of the way it would snuff out the flickering light of some of my most closely held dreams and wildest ideas.
It's not a condemnation of a manager or lawyer or any other role.
It's not even a condemnation of building financial wealth or second homes.
Borrowing from Richards, I see it as slowly allowing the game or institution or status quo to distract you from who you were created to be.
Borrowing from Buechner, I see it as slowly allowing your greatest joy to become untethered from the world's greatest need.
I've always thought that chasing dreams truly was "holy magic behind curtains in a sacred place". Something that was more magic than baby steps and reserved for the select few that knew the secret password to get behind the curtain.
As I've grown up, it seems that chasing dreams or becoming more like who we were created to be is more baby steps than magic and there's no curtain - the hardest part is not giving into the constant call to color up and cash out.
The thing is that coloring up doesn't change the value, only the appearance - maybe it isn't what it's cracked up to be after all.
55 | The Story of the Mexican Fisherman
Sometime in the last decade, I read the following story on the wall of a Jimmy Johns while waiting on my #5 Vito to come off the line. My perspectives on my career and my relationship with money have not been the same since.
An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them.
The Mexican replied, “only a little while."
The American then asked why didn’t he stay out longer and catch more fish?
The Mexican said he had enough to support his family’s immediate needs.
The American then asked, “but what do you do with the rest of your time?”
The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, stroll into the village each evening where I sip wine, and play guitar with my amigos. I have a full and busy life.”
The American scoffed, “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually New York City, where you will run your expanding enterprise.”
The Mexican fisherman asked, “But, how long will this all take?”
To which the American replied, “15 – 20 years.”
“But what then?” asked the Mexican.
The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!”
“Millions?" asked the fisherman, "Then what?”
The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siestas with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”
The first time I read it, and every time since then, I've gotten goosebumps. It paints a picture of the ultimate form of sustainable income - complete work-life integration.
To be clear, this is very different from work-life balance.
There is no scale measuring the amount of work or life.
There is no mental clock keeping track of time allocated to work or life.
There is no black and white distinction between what is work and what is life.
It's nowhere close to being a "workaholic" for any skeptics out there.
There is no finish line, because a finish line would be disappointing.
Work-life integration flips the retirement equation on its head and slowly quiets the longing for “more” and amplifies the call for "better".
The integration leads to generating income from something that leverages natural gifts and skillsets, allows for managing risk of burnout, has a long (or indefinite!) time horizon, and allows time to be spent doing things that matter to you.
That has always seemed more appealing to me than "grinding it out" to a finish line and then calling it quits.
41 | Who’s Throwing the Peanuts?
Don't model your life after a circus animal. Performing animals do tricks because their trainers throw them peanuts or small fish for doing so. You should aspire to do better. You will be a friend, a parent, a coach, an employee -and so on. But only in your job will you be explicitly evaluated and rewarded for your performance. Don't let your life decisions be distorted by the fact that your boss is the only one tossing you peanuts. If you leave a work task undone in order to meet a friend for dinner. then you are "shirking" your work. But it's also true that if you cancel dinner to finish your work, then you are shirking your friendship. That's just not how we usually think of it.
In May 2012, I clipped this excerpt from an article in the Wall Street Journal called 10 Things Your Commencement Speaker Won't Tell You.
It stuck out to me as a 24-year-old trying to find my way in the real world and it still rings true today.
Typically, before you are responsible for supporting yourself financially, you're spoon-fed metrics that streamline measuring progress - grades on report cards, scores on exams, win/loss records in sports, diplomas and degrees, etc.
It can be pretty difficult to orient in a world that doesn't have a standard way of measuring progress - a lot of career and even financial frustration can probably be pointed back to “failure to orient”.
Because it's so hard to find metrics in the real world, it's easy for income - one of the few things that spans household, profession, industry, and age - to become a default metric of progress.
Some level of income is vital, but beyond that level, it is a pretty lousy metric that doesn't account for the things that add all the color to life, particularly the quality of our relationships.
The line that hooked me was, "But it's also true that if you cancel dinner to finish your work, then you are shirking your friendship."
The quality or strain of a relationship is pretty easy to feel, but impossible to objectively measure.
With enough shirking, I think it's possible to get "fired" from a relationship. It's just a lot harder to recognize when we're on the brink in a relationship because there aren't any peanuts being tossed.
Oftentimes, work must be prioritized - not minutes at work, but real, value-creating work.
Oftentimes, a relationship must be prioritized too.
The nuance isn't in knowing precisely when to lean into each one.
The nuance seems like knowing that the peanuts aren't the only way to measure progress and figuring out creative ways to assess progress for the things that might not have peanuts.
37 | The "Single Jump" Myth
In a conversation with a friend, my wife came up with a fantastic metaphor for pursuing career change.
The metaphor can be extended to anything where there is a vision that is grander than the current reality - assembling a group of people, starting a business, or even running a household.
Pursuing any change is a lot like trying to get from one side of a river to the other.
Our modern-day habits of small talk and social media have led us to believe that some people can make it across the river in a single jump.
No one can cross a river in a single jump...I promise.
There are two troubles with the "single jump" myth.
The first is that it makes change seem easier than it is, which is pretty discouraging when your first jump ends with a splash.
The second is that it makes it seem like there is more to be found on the far bank than there is in the river.
In reality, change is more like gradually jumping to different rocks to get closer to the far bank.
Some rocks are huge, easy to spot, and bone dry.
Some rocks are bunched closely together, and some rocks are far apart.
Some rocks are tiny and hard to spot initially but are the only way to keep making progress.
Some rocks are wobbly or slippery (or both!) and require extra care landing on them, standing on them, and leaping off them.
Sometimes your shoe, maybe even your sock, gets wet.
Sometimes you hit a dead end and must retrace a couple of steps.
Sometimes you might have to avoid the rock with the snake on it.
As I have pursued career changes, the process has made me more confident that you can't make it across the river in a single jump - all you can do is find the next rock.
The process has also made me wonder if the far bank is what we're pursuing or if the pursuit is actually the rock jumping itself.
Additional Reading
What’s the next smallest step? by Carl Richards
Reminder that scary things are less scary when you make them smaller.
You Accomplished Something Great. So Now What? by A.C. Shilton
Easy to read introduction to the "arrival fallacy".
118: Start Small by Emily P. Freeman
"Small things don’t always turn into big things, but big things always start out small."
18 | Barometer on Burnout Risk
Burnout is dangerous.
Some of the consequences are obvious and easy to measure - the potential loss of an income stream, the stress caused by an infinite email stream, or the persistent feeling of overwhelm as you start another day.
Some of the consequences are deceptive and maybe impossible to measure - the impact of bitterness towards your colleagues, apathy towards your work, or future options slowly falling off the table.
Acknowledging it's dangerous is a start. Keeping tabs on it seems like an integral skill.
It's hard to measure, because it's the kind of line you can't see until you've crossed it.
Counting down to the weekend every Monday morning feels like burn-out risk is trending higher.
Pleasure reading about "work" topics during free time feels like burn-out risk is trending lower.
When you find yourself saying "I deserve this" as you sign off and head on vacation it might be trending higher.
These aren't the kinds of things that get fixed overnight, but they can change over years.
It's easy to think a 10% raise is the highest impact thing you can do for your finances.
It's easy to measure. It's easy to see when it hits the bank account. It might be in your control. Like ibuprofen, it relieves pain...temporarily.
A 10% reduction in burnout risk is a whole different category.
You might feel it immediately or maybe you won't.
It's certainly not hitting a traditional bank account.
But...it might help you discover something that you hope you get to do forever or breathe life into a stale routine or provide the opportunity to connect with family and friends that hasn't existed before.
You’ll never be able to measure any of these things, but maybe that’s a sign that they’re worth it.
Additional Reading:
"You Better Love This" by Morgan Housel
"Mexican Fisherman and the Investment Banker" by Unknown Author
6 | Meandering Through the Cone
I had a conversation with a friend who has dreams of a radical career change.
He had already started to converse with people in and around the industry. He had already started building up income and setting aside cash surplus. He had a recently developed understanding that it's a long race and the power of compounding applies to relationships, knowledge, and habits just like it applies to money.
After sharing what seemed like incredible progress, he asked, "What else should I do? What's next?"
Persist, my friend. I didn't know what else to say.
For 10+ years, I have been pursuing a new vision of helping people with money.
I have seen plenty of people do exceptional work helping people with money, but I have never seen my vision in practice.
Along the way, I have had...
Infinite conversations that had useful nuggets and useless nuggets.
Career changes that directly contributed to acquiring experience and included extra responsibilities that felt like a drag.
Continuing education that pushed me forward and felt like a waste of time.
Reading, tons of reading, much that felt relevant and much that felt totally worthless.
Writing that forced me to crystallize thoughts even when I felt like I had nothing to say or the ideas felt too abstract.
In the conversation with my friend, I described it as feeling like I was in a giant cone.
At the start, the vision had infinite inputs and outputs that all fit into the top of the cone.
As conversations, career changes, reading, and everything else happened, I began to "intentionally meander" into and through the cone.
I have never known my precise location in the cone, and I don't believe there is a bottom.
There is a no destination - only the refinement and clarity that comes from moving down the cone.
When it comes to desiring change and casting a vision, I think the most important thing is to get in the cone, stay in the cone, and see where it leads.
Helpful Perspectives
The lonely unicorn by Seth Godin
3 | Professional Bravery
In a recent conversation, a friend shared an anecdotal observation that "professional bravery" within careers seems to start drying up somewhere in the 40s for many people as the reality of the career slog sets in.
The specific example in the conversation was a pastor counting down the Christmases left before "getting" to call it quits on a career. The countdown had started with 20+ Christmases to go, not 2.
Initially, you might gasp, but I think there are countless other examples of this perspective across every field, and I don't think we need sophisticated research to confirm it.
Innovation and ambition replaced by status quo and not rocking the boat.
Working for a purpose replaced by working for an income.
The flexibility and freedom offered by change replaced by the hypothetical cost and fear of change.
Life circumstances certainly play a role - many of which might be out of our control.
I still think there are at least two things that are always in our control but have a sneaky way of slipping through our hands if we let them.
Slowly losing clarity on the "why" behind what you spend your time doing.
Slowly tethering your lifestyle to a specific, high level of income.
I think the combination of these two things is deadly when it comes to professional bravery.
When we stop the process of editing and refining our "whys" and our lifestyle, it seems like "professional bravery" is going to slowly start to evaporate.
1 | The Gap Between Plan A and Plan B
Plan A is what you're pursuing now.
Plan B is what you'd pursue if couldn't pursue Plan A.
The bigger the gap between Plan A and Plan B (and I'm not just talking about money!), the greater the chance of disappointment and the more fragile Plan A becomes.
When you're looking for a new home, the moment there isn't a Plan B is the moment you've lost all bargaining power and invited a disappointing outcome to the party.
When you're negotiating income, the moment there isn't a Plan B is the moment your boss tells you what your new income will be.
When you're taking kids out for dessert and Plan A is closed, I hope you have a Plan B.
Plan B is not a synonym for paranoia or worst-case scenario.
Plan B ensures you know the alternative and next steps if needed, but Plan B also strengthens and stabilizes Plan A.
Exploring and defining Plan B can also breathe new life and purpose into Plan A.
Seth Godin has said, "Power might be in the form of money, access to plenty of lawyers, or simply a willingness to burn it all down to the ground."
It's easy to skip over that third option, because the first two seem so obvious.
"Burning it all down to the ground" seems a bit intense, but being willing to walk away, pivot, start over, or try again is a choice that’s available all the time.
What's your Plan B?