Mind on your Money, Time and Freedom
Making the bed, biding time, and the Second Rule of Fight Club
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
Last week, I wrote about time management and better managing one's mind. But I left out a whole bunch of stuff.
I completely missed the two essential concepts of Time: Money and Freedom.
Money and time are often linked. We spend time, save time, invest time, and buy time.
Freedom is entwined with time, too. There’s free time, leisure time, time off, flex time, and downtime.
In Part Two, I will share ways to improve your life by making better daily decisions about time, money, and freedom. I’ll start with the basic, tactical choices and ladder up to big-picture strategy with a personal story from my childhood that still drives me today…
Do the Chores, then You’re Free to Play
Is there a more simple, timeless lesson from our childhood? When you’re a parent, words like this come out of your mouth without thinking. We’re channeling a deeper meaning when we repeat this directive: When we manage ourselves well, we have more freedom and better lives.
I’m still working on building better habits around the basic stuff in life. I should do the dishes, take the trash out, and make the bed. I should throw those papers away, respond to emails quickly, and move my savings account to a bank with a higher interest rate. I’ll do it later…there are so many other, better things to do!
But a messy kitchen, desk, or inbox is a messy mind. We see the chore that needs to be done, and while we might push it off later, it still takes up space in our heads.
I’ve had some success following William Stafford’s Daily Rule: Do the hard things first. We do them first when we have maximum energy. When they are complete, we get to do the fun stuff, which we need less energy to get excited about.
I also find something freeing about seeing an empty inbox, tidy bed, and clean desk. It’s a feeling of accomplishment and mastery of your domain. Doing these little things helps us feel like we have more control and freedom.
Finally, once you program yourself to do these chores, you no longer have to consider them. It just happens, and you are free to spend your valuable time on more important and exciting activities.
Make Time for What’s Priceless
My younger daughter is staying with us this summer before she heads off to her senior year of college. She is majoring in animation, so it was no surprise that she had to see a one-day screening of Puss In Boots: The Last Wish at the tiny local theater. It was surprising that she asked me to go with her. She knows I’m not a big animation fan, and I have other things to do at 1 pm on a Tuesday.
So, of course, I said, “Yes.”
The older she gets, the more interesting she is. But she has her own interests and friends, so we get less quality time together than when she was small. After school, she will likely be off to a bigger city with an exciting new independent life. So I’ve got to soak her up while we have her home, which means sitting in a theater crowded with little kids. It was priceless.
As an empty nester, I often advise my friends with younger kids to soak up their time together. You’ll never get it back. Thankfully, most of us work in places today that recognize the importance of family time and parental involvement. Never feel guilty about prioritizing soccer games, piano recitals, and parent-teacher conferences. Work will wait for you.
Buy & Bide Time
Again, so many words link money, freedom, and time. Three separate points are worth breaking out here:
Spend money to save time - I’ve found that one of the best uses of money is to increase the quality and quantity of my available time. You can always make more money—through work and the miracle of investment income—but you have only so many hours in the day and days of your life. This can feel like wasting money because the dollars are “real,” and the return on time you get is more complicated to predict. But you’ve got to trust the awesomeness. Some examples that work wonders for my family have been a house cleaning and lawn service, meal kit subscriptions, and local guides on international trips. These professionals save you time and produce much better output than do-it-yourself. Even though I am a keen toilet scrubber when called upon.
Buy time during big decisions - Never move quickly when you’ve got a large life or work choice to make. For example, a short delay might allow time for more information or a better offer to come in during a negotiation. But it’s a meta lesson: “Sleeping on it” gives your unconscious mind the chance to process. It’s like an internal board meeting that takes place when sleeping, showering, or working out. Put your internal team to work, and if someone gives you an unreasonable deadline, that’s a sign to say “no.”
Bide your time when you need to - Sometimes in our work lives, we feel like prisoners. We don’t like where the company is going, we’re bored with our work, and our manager is a P.I.T.A. You read and hear about other, more exciting companies and careers and wonder why you’re wasting your precious time in this place. I’ve been there and gotten out to do my own thing. But I’ve also sucked it up and stuck it out for many years when it was the smarter thing to do. You might be under contract, have two small children at home, or the job market could be trash. Such times happen, and it can be wise to stick it out. But you don’t have to be a prisoner inside your mind! How can you turn this situation into something you can learn from?
Put a Price on Your Time
One of the many reasons it pays off to work where you’re billing hours to a client—like as an accountant, consultant, attorney, or creative—is that you get used to the idea that time is money.
But you don’t have to do a tour of duty in those fields to understand the main point: Your time is valuable, so come up with a daily rate to ensure you’re “billing” wisely.
Naval puts it better than I can: “Always factor your time into every decision. How much time does it take? It will take you an hour to get across town to get something. If you value yourself at one hundred dollars an hour, that’s basically throwing one hundred dollars out of your pocket.”
This is especially important when you commit to spending considerable future time on saying “yes” today. I accepted a position on a startup’s board of directors a few years ago. It was a two-year commitment with compensation of $25,000 in stock options. The work involved quarterly board meetings, travel, conference calls and emails. My rough estimate is that I spent 400 total hours doing this work. So, my hourly rate was effectively $62.50.
The reality could be 2-3x higher or go to zero, depending on if and when the company sells, but it takes a while for that to happen. This rate is much better than the $3.85 minimum wage I made at my first job sacking groceries at Kroger, but I’ve gotten a lot more valuable since then.
If such an opportunity came to me today, knowing what I know now about the hours involved—and my dislike of being on boards—this would be a hard pass.
Now, please don’t think of everything you do in time value of money. You can create a lot of mutual value by volunteering your time to friends and important causes. This Social Capital and the life experiences and lessons that can come with donating your time are often priceless. However, putting a price tag on your time can help you assess the opportunity cost and ensure that real value is being created.
Freedom from Stuff
Do you remember the First Rule of Fight Club? Of course you do. But we can’t talk about that…
Do you remember the Second Rule of Fight Club? That’s something we should talk about a lot more:
“The things you own end up owning you” - Tyler Durden
I’m writing this from a cabin on a lake in northern Michigan, which my wife and I bought with proceeds from the sale of my last company. It’s a wonderful area of the country that we visited many times before deciding to invest. The lake and surrounding trees are a wonderful escape from the city. And when the rest of the country is 90 degrees in heat and humidity, it barely breaks 75 here.
But buying this cabin added a ton of chores to our list. Maintenance needs to happen whether we’re here or not. The builder screwed a bunch of stuff up that I’m still fixing. When we leave a chair on the dock, there’s a decent chance the wind will sweep it into the lake—and I’m the one who has to swim it back. And these goddamn chipmunks are desperately trying to store nuts under our fancy stone sidewalks.
Cue the world’s tiniest violin…
The point is that buying stuff with the winnings from your luck and hard work often comes with less freedom and lost time. Plus, if you buy things to make yourself happier, you will discover that the promised happiness never comes.
Our lake place is worth the additional time and money, but I now frequently think about what stuff we can eliminate to simplify our minds and reduce the time tax. One thing that worked out was downsizing to a smaller home after our kids moved out. We filled two dumpsters in that move and found a home downtown that requires zero yard work. After countless hours pulling weeds, it’s still spooky to have that time freed up.
Again, the key here is mind over matter.
A Personal Strategy for Money and Freedom
“The only thing that worries me in life is money.” —Churchill
Yeah, that’s the Winston Churchill, a genius strategist and inspirational leader through World War II. For all of his brilliance, he couldn’t keep himself from his bad spending habits, and his debts chained him throughout his life.
We must learn from Winston and countless others to think more strategically about our money, time, and freedom.
Strategy is a fancy word for “educated decision.” You (and your life partner) will build a better life together by consciously choosing an approach. It might be to grind and save for retirement when you can travel the world. You might keep your burn rate low so you can work as a part-time contractor and surf or hike whenever you want. It’s up to you; just pick a strategy—any strategy—and stick to it.
From an early age, my strategy was to earn enough money to buy work freedom. This strategy mainly came from seeing my Dad struggle in his career.
My Dad, Bob Gilbreath (I’m a junior), began his career as a civil engineer and wrote a textbook on project management before taking a leap into management consulting at Arthur Anderson in the 1980s. This was years before the consulting arm would spin out into Accenture. My Dad was a founding member of the Change Management practice within the firm. He did well, traveled the world, and advised giant companies and governments.
He eventually tired of the big company consulting world and wanted something more of his own. Dad got an offer to be the number two executive at a much smaller firm. It came with more money, more upside, and a chance to drive the ship. I remember his excitement in spreading his wings. At a very young age, I was already dreaming of my own business career and following in his footsteps.
But as the months progressed, I heard my Dad’s enthusiasm fade at the dinner table each night. The Founder/CEO of his new firm treated the team poorly, didn’t listen to others’ recommendations, and had no interest in sharing power. Eventually, my Dad was out of a job.
Then, the economy dived, and there was less interest in his services. He was out of work for a year. We were all scared.
I remember Dad calling me shortly after the start of my freshman year of college. He was worried about being able to keep me in school. Financial aid offices aren’t used to seeing a parent’s income go to zero.
But he swallowed his pride and figured it out. Dad hustled for side gigs and worked for people he didn’t like. He even stood in line at the unemployment office.
Living through his experience was formative for me.
Flash forward several years and I was working in my first major corporate job at Procter & Gamble. I was doing very well, but it was increasingly crushing my soul. Ahead of me was a career of checking boxes and playing politics. I yearned to stretch my wings and earn enough money to break free.
That’s when my friends offered me a job and some equity to join the digital ad agency they were in the process of turning around. At that point, I supported two kids under age 4 with my single income—and I was still making student loan payments. This was two years after the dot-com crash when I saw many friends’ dreams of riches go up in smoke.
I spent three months considering their offer. I feared going through what my Dad did. Hell, my Dad couldn’t believe I would entertain leaving P&G.
But I made the leap. I had to. I’m my father’s son.
I’d rather live with my own dumb decisions than execute someone else’s dumb decisions. I yearned for the chance to put my butt on the line and to be rewarded with a nest egg for life. My wife was thumbs up, too. She’s always known me better than I do.
Luckily, it worked out for me. We sold the company, and my ownership stake gave me the freedom I always hoped for. Our most significant spend was paying off our student loans. The next was writing a check as the founder of my first startup. That eventually worked out, too. Seeing and feeling my Dad’s struggle helped me succeed.
I’m so glad Dad got to see me achieve what he couldn’t quite achieve. He passed away of a brain tumor ten years ago—two days after Independence Day. I’ve been thinking about him a lot lately.
To me, July 4 isn’t just about the birth of our nation. It represents the power of freedom, of following our call to adventure. We should follow when called. We owe it to those before us who had to struggle for freedom, and we owe it to the future, which can find infinite benefit from the positive acts we take today.
Despite all its messiness and imperfections, our democratic, capitalist system provides tremendous freedom and has a decent safety net. So take a risk. Get in the game. Go for it. We’re all here to help.
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BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Anne Mahlum - fearless entrepreneur
There’s no content I love more than hearing company founders discuss their origin stories on podcasts. A few weeks ago, Built to Sell invited Anne Mahlum to talk about investing her life savings on a fitness concept that she later sold for over $100 million.
What I love most about Anne is that she had a vision for what a single facility could become and dictated the terms to get there. Despite never starting a company or raising money, she worked the system like a veteran and left on a high note while turning over the keys to capable leaders she developed. We can all take a lesson from her courage and determination.