It's Not F-You, It's F-Me

Have you considered these paths to career and life freedom?

Welcome back to The Workaround. I’m Bob 👋

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Helpful reminder on the Traverse Area Recreational Trail near Sutton’s Bay, Michizen.

Lately, I’ve been on a bit of a negative tear in my writing. I touched on bad bosses and harmful products. Then I shared how feel-good companies often have a very dark side.

But I’ve been mostly preaching to the choir. You already know it’s rough out there. In the U.S., 57% of people are dissatisfied with their jobs. Globally, “four out of five employees say they are not thriving at work. More than half of those surveyed say they are struggling with stress, aren’t happy with their jobs, and don’t feel their work has purpose.”

I’m not a math major, but I think that adds up to a few billion people trapped in some level of workplace hell. I mean, they must be trapped—or why would they stay in these jobs?

The traps sure are elaborate: Paychecks, health insurance, stock options, annual bonuses, non-competes, peer pressure, economic worries, and fancy titles. They combine to keep us playing the worst game ever; toiling in the mines for resources and XP, and endlessly sharpening our pickaxe, but never setting out on an adventure.

But the potential for freedom is out there! Mostly, we long for a financial nest egg that would let us quit our crappy jobs. You know: “Fuck You, Money”—the chance to tell your awful boss to take this job and shove it.

I think “F-You” is too negative. It just gives the middle finger to another trapped person on our way out the door.

I’d rather focus on the more critical F-word: Freedom. This is what we really crave. We want to free ourselves of these hellish work bonds. We want the freedom to find meaning and live our best lives. Free Me. F-Me.

And a big pile of money is far from the only way to get there.

But the only person who’s going to free us is ourselves. To escape, we must take agency, form a plan, and act. Here’s inspiration to get you started:

F-Me Money

Money is the only belief human beings share. No other source of power in our lives is more dominant than money. Sadly, it eclipses love, beauty, and fellowship. We judge our success and status through cash. We determine our value to a company—and compare ourselves to others—by the number on our monthly paycheck. And our moods mirror the daily direction of cash value in our business budgets, investment portfolios, and personal bank accounts.

Mostly, we fear what will happen to us and our families without the reliable flow of money.

So we all have a price—a dollar amount that will buy our mental freedom. It might be an offer from another company that convinces us to take a risk on a new job. Or it’s what our financial advisors tell us we should sock away before we retire. And we might have, or dream of, a lump-sum windfall from selling a business we own. This was a significant motivator for my own entrepreneurial path.

But there are a growing number of ways people are adjusting how they plan their lives and think about money that offer more freedom.

First, we tend to forget about the rate of spending—and how we may gain greater freedom by reducing our burn rate. I have a few friends who make well over $300k/year, yet live paycheck to paycheck. Eventually caught in a layoff, and with few of those high-priced jobs available, they’ve been forced to accept work they dislike—that keeps them away from the families they support—to keep the new luxury clothing, cars, and vacations rolling in. But any child, at any age, would gladly give up this stuff for more quality time with their Mom and Dad.

If we can free our minds of the need to keep up with others, or the idea that thinking more stuff will give us solace,¹ we give ourselves an immediate raise, a clearer mind, and a more stable, grounded family. Is there a better investment?

Cutting burn rate might also make the math work on a lower-pay, higher-meaning profession. My friends who teach at universities could make much more if they went back to the corporate world, but they would never trade that for the positive impact they now have.

“People who live far below their means enjoy a freedom that people busy upgrading their lifestyles can’t fathom.”—Naval Ravikant.

Second, the price of F-Me might be less than we think. Entire communities are forming around peers who help each other explore new strategies for retirement saving and spending. There are financial planning and health insurance products that let you avoid saving for every disaster scenario. Heck, many people retire and die with far more wealth than they or their heirs need to live comfortably.

There’s also a growing trend of using savings to buy freedom for what matters more in life. I’ve seen friends use winnings from a company sale to take six months off to focus on family or personal creative projects.

Others save F-Me money to take a significant career risk, which gives them a chance to see if they can create the job of their dreams. Paul Millerd calls this Leap Capital: “a specific quantity of money or other resources and an accompanying story that someone uses to convince themselves that it is reasonable to make a change in their work life.” He says it almost always shows up in the following formula:

I have $X, which means it’s reasonable to take risk Y for Z period.

My buddy Paul had an idea for a startup he couldn’t stop thinking about. But as the sole breadwinner with young children, he couldn’t leap. For years, he kept his lucrative day job and socked away enough F-Me money to give himself a year to make it work. He waited patiently for an inevitable exit package and pulled the trigger. Paul survived this first year, and his business is taking off. But even if it failed, he bought the freedom to take a risk without compromising his family’s security.

F-Me Skills

When we acquire a very particular set of skills. Skills we have acquired over a very long career. Then these skills make us a godsend for businesses in need.² These are F-Me Skills.

Cal Newport calls this being “So good they can’t ignore you.” It comes from putting ten thousand hours into work that is needed, recurring, and somewhat rare.

Many companies I know have a “unicorn hire” need:

• A founding sales AE who knows how to win the company’s first five customers in media-tech.

• A cybersecurity specialist who can help legacy businesses prepare for Department of Defense vendor audits.

• The ecommerce expert who understands how to work with non-profits.

The neat thing about developing these skills is that we usually build them around work that we love. Unless we’ve got a crazy parent or teacher forcing us to do something until we bleed, it’s just too hard to get really great at something we don’t enjoy. So there’s a freedom that comes from choosing to specialize in what we enjoy.

Once we get these precious skills—and see their market value—we have expanded freedom to write our own path. Contract for multiple companies at the same time, lock in premium rates, and even pull similar unicorns together into a consulting business. Or enjoy a flexible lifestyle, working with whoever, whenever, and wherever feels best to us.

These skills give us powerful confidence to stand up for ourselves and quit if that’s what it takes. In our podcast conversation a few weeks ago, Peter Williams shared how he negotiated hard for an ownership stake, knowing he could start his own company again if he didn’t get it. That’s F-Me Skills turning into confidence and opportunity.

A big watchout here is thinking that degrees and certifications will make this path work. Loading up on debt hurts your financial freedom. Studying enough to pass a test won’t get you much more than an extra point on an AI resume scan. Thanks to a flood of executive courses, almost everyone now has a Harvard degree of some kind. F-Me Skills come from proving ourselves able to do the work, and there are lots of ways to learn for free and test ourselves in the real world.

F-Me Network

A woman named Sophie was introduced to me by a mutual friend. She had moved to town five years ago when her husband went to medical school and got a job at a large local marketing company. But she was affected by a round of layoffs and found herself out of a job, with virtually no local connections to help her. It was a big wake-up call. She eventually found a new gig several months later, having learned the lesson of building connections.

Another friend, Dana, was also laid off recently. But by the end of her second week, she had three full-time offers and two paid consulting gigs. That’s because Dana spent a decade purposely building relationships in her industry. She knows everybody, and everybody knows and likes her, which means we all want to hire her when she’s available.

This is the power of an F-Me Network. You have so many people in your corner that you can take more career risks and quit jobs that turn bad.

For the introverts in the room, note that this isn’t about becoming the life of the MeetUp or remembering to hit like on fifty LinkedIn updates a day. But it does take some regular effort.

First, we’ve got to be known for doing great work. Usually, this comes from excelling in our current jobs so that our co-workers see our impact. This means going beyond just meeting expectations to find remarkable ways to add value and help our peers. This side-by-side partnership shows co-workers that we have strong capabilities and character. They’ll remember us in their future jobs and recommend us for a role or help us get a direct intro to HR. After all, it’s in their interest to fill their company with great peers!

Second, we must invest regular time in meeting new people and ensuring peers in our past remember our value. You might join industry groups or meetups, volunteer in your community, organize a happy hour, or schedule one coffee meeting every two weeks. Whatever it is, commit to something regularly, and the value of your F-Me Network will grow over time like compounding interest.

I’ve turned this Substack into a fantastic way to meet new people and keep in touch with peers I worked with decades ago. By writing regularly with helpful posts, I attract new readers and stay on friends' radars. I’ve become known as a guy who is willing to help. Thanks to Substack, I “own” my audience and get to send direct emails, rather than relying on LinkedIn's feed algorithm. After all, it’s not your F-Me Network if another platform owns your contacts’ info and attention.

In my posts and podcasts, I feature my “Office Hours” open calendar link below so I can make time with anyone. Every week, this brings me a handful of interesting Zoom meetings. After each discussion, I log a few notes in an Excel sheet that I use for searches and reminders in years to come. People are often amazed and thankful that I give them my time this way. But here’s a secret: (1) it’s just a few 30-minute meetings; (2) I don’t have to prepare for them; and (3) I learn as much from these people as they learn from me.

If you can’t think of anything else to do, try this one thing: Make time for people in need. When anyone asks for help, an intro, or advice, say yes immediately. Everyone is busy, and most people ignore such requests, so making an effort makes a significant positive impression. And while it’s not always quid pro quo, if we can be there for people, the karmic forces of the universe tend to reward us when it’s our turn to ask for help.

F-You, Ego

Despite all of these well-worn paths to freedom, I’m amazed at how many people stay committed to self-imposed mental prisons.

A few weeks ago on the Built to Sell podcast, Tad Fallows shared insights from a post-exit entrepreneur community that he founded. This group of over 6,000 members has an average net worth of $15 million.³ Their conversation turned to how these Top One-Percenters feel about money:

“Everyone says they need double what they currently have in order not to worry about money. $100MM seems to be the point where they don’t worry anymore. Most keep doing some work because they hate the feeling of not seeing a paycheck coming in.”

You read that right. These winners in the game of business, who have almost everything money can buy and who have skills, networks, and risk-taking advantages beyond compare, are still not free. Money fears continue to fill their minds.

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.”― Jim Carrey.

We see this in the behavior of public billionaires, too. They push to capture ever more attention, power, and money, while competing over which has the largest yacht displacement and longest rocket. Their companies, which once promised to connect society or serve as a bastion against evil, have found ways to rationalize everything from propping up dictators to encouraging teens to drop out of society. And it’s all for another dollar that they will never be able to spend in their lifetimes anyway. You can only sail one yacht or ride one rocket at a time.⁴

Of course, they’re all just people like us, going through a process that most humans experience. In this post about a nurse who recorded the last words of over 300 dying patients, a common theme is regret over the fears that held them back. Like the retired engineer who said, “I was so scared of being poor that I became rich in fear.” Or the CEO who told her, “I mistook being busy for being alive.” For a culture so afraid of death, I’m surprised how little advice we take from those who are on its precipice.

This seems to be the lesson playing out before us right now in developed nations: Money rarely ends fears or unlocks freedom. The only way out is to free our minds.

The world needs these leaders to take on a second, meaningful act. Imagine if these billionaires and post-exit entrepreneurs put their fears aside and focused their full energy and passion on solving bigger problems. They have demonstrated a rare, precious combination of creativity, innovation, strategic thinking, networking, and an ability to build and inspire teams to achieve long-term goals.

We’re in a fucking trash fire right now—but they’re busy checking the stock market every five minutes!

The Price of Freedom

Pot, meet kettle…

Hi! My name is Bob, and I’m a post-exit entrepreneur who is also struggling to figure out what to do next. I’m on Year 5 of this process. I only look at the stock market once a day, though.

Once we’ve finally won financial freedom, we’re often left unsure what to do with our lives. The easier road most taken is to get back in the game and keep running up the traditional success scoreboard. That’s the mentality behind “I just need to get to 9-figures and then I can relax, find meaning, and spend time with the family.” And that’s the path I spent years going down again after selling my last company.

I recently rediscovered a similar example of legendary NFL coach, Bill Walsh, written by his son, Craig:

“In some ways, my father’s life was almost Shakespearean, because what got him to the top professionally was his downfall personally; in spite of his incomparable achievements, he had trouble ever feeling fulfilled on a continuing basis. Driven by a desire to gain the stamp of approval from his peers, he was consumed by work and winning, increasingly haunted by losing. When you achieve what he achieved, the inability or unwillingness to grant yourself happiness and satisfaction is tragic.”

Achieving status, power, and money is a game that’s always available and encouraged by society. This way is well defined and has plenty of people standing by to share in our success. But it can be a distraction—often an addiction—that accumulates ego debt that must be paid at some point. This is the source of many burnouts, divorces, and midlife crises.

Mercifully, I hit a breaking point that was easier than most. I chose to make my full-time job about seeing through my bullshit and scraping off egoic defenses, projections, and attachments. Trust me, there’s plenty of stuff to keep you busy in this job!

Over time, in fits and starts, I’ve begun to free myself. The process starts by realizing we don’t have to think, react, or behave as we have in the past. And we don’t have to go along with what we think society expects from us. It’s kind of like a second birth and growing up.

I’ve never felt better, despite no longer “being someone” or leading anyone.

Now I’m back into the business world, but in a different way. I help other service business builders get off the ground and write regularly here in that spirit of enabling others. It’s a small commitment so far, freeing time to keep up the self-work and leaving room for whatever the universe has planned once I finally finish my baking process.

So, when you finally win your F-Me freedom, take a break from working for the next nickel and start working on yourself. You want the next big challenge? Try sitting alone in the dark for 30 minutes, facing problems from childhood that resurface spontaneously, and learning that every belief you’ve ever had has held you back.

You may reach heights of insight and ecstasy that no amount of money can buy, yet there’s no photo to share on Instagram and no one who understands your unique experience. There are no brags, humble or otherwise, in these deep waters…which is kinda the whole point.

There’s a whole new world inside of you waiting to be discovered. It’s a wealth of joy to experience and share with your loved ones.

You are the job of a lifetime.

“Few manage to see beyond their material desires; if they did, they would understand that what truly lies behind those desires is the longing to obtain something greater.”—Jungian Alchemist.

If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏

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1. Usually takes some serious soul-searching or therapy to dig out what’s really driving it.

2. Made ya look

3. Minimum $2.2 million in investable assets to join, most in the $5 million to $100 million range.

4. Well, technically, you might need two if you’re Jeff Bezos. He has a $500 million sailboat, plus a $100 million support boat that follows along. It houses all the toys for the parent yacht, of course.