6 Tools for Reinvention, or The Plight of the Platypus

Across a hundred or more eerily similar conversations with mid-career creatives, I’ve noticed the same concern simmering below the surface. With some gentle prodding these folks will take the lid off the pot and voice it: “Is something wrong with me?”

They can’t help but ask this question because they are in their thirties, forties, or fifties with a colorful collage of gigs, projects, and ventures, and they still don’t know what they want to be when they grow up.

When they see friends and acquaintances who have had several jobs recognizable as a career, they aren’t envious, per se, but they can’t help but make comparison.

Despite ample evidence that they’re good at a variety of things, they wonder if maybe there’s a problem. Maybe there’s a wire loose. Maybe they need to be fixed.

I think of this as the plight of the platypus, and I’ll explain it further before I point out three traps and give you six tools for moving forward with confidence. You’re fine the way you are, and you can have more satisfaction in your work and joy in your life.

But you have to move like a platypus, not like a Golden Retriever.

The Plight of the Platypus

Some of us are multi-faceted, multi-passionate, and multi-potentialite. As multis, we’ve got a diverse set of skills and capabilities that don’t ordinarily go together. Some of our parts even seem mismatched, like a platypus with its duck bill, waterproof fur, and beaver-like tail.

That versatility is a gift, but it complicates our work and careers. Our education doesn’t prepare us to navigate a hyper-specialized workforce with no obvious place for us. No wonder so many of us end up self-employed.

Still, I’ve found myself wishing that I could find The Thing. Wouldn’t life be simpler if I was happy spending most of my time on logistics, nursing, or fixing cars?

If I found The Thing, then it could be the lantern that pushed back the darkness of my uncertainty. It would fix my allergy to doing just one thing.

Surely platypus with a lantern wouldn’t be plagued by second guessing the path he was on or get tossed around by whatever emotion was blowing, from confusion and frustration to sadness and grief to tiredness and near-resignation. He could silence that voice saying, “Something is wrong with you,” and throw himself fully into The Thing. He could experience real, lasting momentum. His career path would feel less like trudging uphill in dense fog and more like coasting downhill on a bicycle.

As a platypus, I want two things: a mind quiet and confident on the subjects of work and career and the momentum that would come with clear commitment to a single direction.

And as a platypus, I’ve been left with more questions than answers:

• Why do certain former colleagues, siblings, and friends with well-blazed career paths get promotions, titles, and raises when they don’t seem especially brilliant, no offense?
• Why can’t we, the platypuses, be more like them, the Golden Retrievers, and be happy doing one or two things for decades?
• Why can’t we just decide and commit already?

If I’m honest, I want focus and variety, and I have carried these two competing desires like an arrowhead in my heart. Evidence of what being unfocused has cost me deepens the cut.

Other platypuses find their way to me after they stumble across an essay or podcast episode and realize that I’ve spent some time thinking about the plight of the platypus, which fundamentally is about having a wealth of skills, opportunities, and possible paths in a world that rewards specialization.

Our optionality is paralyzing, and I would like to offer some reassurance then some advice.

Nothing is wrong with you.

Here is what I have to say to the platypuses reading this: Nothing is wrong with you.

Maybe you do need to change some things about yourself, but being a platypus isn’t one of them. God put a disco ball of potential inside of you that shines many directions at once. God loves how you are made, and you can rest secure in that fundamental belovedness.

What is equally true is that being a platypus who is pretty good at a variety of things means that you need a different way of thinking about your work and career and your relationship to them.

You don’t need to know what you want to be when you grow up, but now that you are grown up, you do need to know how to keep reinventing yourself, as needed, without slipping into the old pattern of self-doubt, quitting things too soon, or not quitting them soon enough.

A platypus can get caught in traps that a Golden Retriever easily avoids, so you need to be aware of them. You also need a different set of tools to find your way forward.

I’ll explain three of the most common traps before I share six tools that have been helpful to me.

Trap #1 - The Fallacy of Certainty

The first trap is what I call the “fallacy of certainty.”

On any given day, we don’t know what will happen to us, good or bad. We have no choice but to get dressed and get on with the day. We know that roughly half of marriages end in divorce, including those where both partners felt very certain on their wedding days. We still exchange vows.

We order a salad at lunch, knowing that it’s good for our waistlines and cholesterol. Meanwhile, any healthy choice can be rendered irrelevant in an instant by a car wreck.

We’re used to acting without certainty in big and small decisions, so why is it that when we’re trying to decide what to try next, work wise, or where to take our businesses, we suddenly dig in our heels and act as though we must wait to be sure?

In my case, one of the reasons is because money is on the line and I have three kids. When the stakes seem high, I tell myself that I need more research, information, advice, clarity, expertise, credentials, repetitions, and confidence before I can proceed. I try to reach Certainty through its secretaries, Preparation and Control.

Subconsciously, I fall into the fallacy of certainty. I act as though certainty will save me from dead ends and wasted time, from costly mistakes and embarrassment.

Ironically, while I wait for this wizard on the white horse to deliver me, I dither. My delays seem reasonable, strategic even, because I can point to times when more preparation would have yielded better results. If you have ever botched a speech because you didn’t rehearse enough, then you know what I’m talking about.

But entering that wide territory where our work and our heart intersect isn’t like rehearsing a speech or anything else where we already know how to get better results. And Certainty with a capital C is an unreliable wizard. Certainty rarely shows, and even then, the wizard doesn’t deliver the safety, confidence, or bags of money as promised.

And our sense of readiness before we act is rarely an accurate indication of how rewarding a pivot, transition, or foray will be after six or twelve months.

Have you ever been surprised by your enjoyment of a certain project or type of work that you would have dismissed out of hand had you not stumbled into it?

Or have you landed a project with a big brand or a cool client in a market you wanted to break into only to watch your enthusiasm swirl down the drain as the people or circumstances made it decidedly uncool? I have.

We cannot know how everything will turn out, so we do the only thing we can, which is make a judgment call and scrape together enough courage to take one step, and then another.

Confidence in the path comes not from waiting and thinking more about the act but through acting. Each new step brings fresh feedback and intelligence. Each step brings a richer understanding of our recent hesitancy and our real desires.

You and I already know this from experience. I didn’t have to know if my wife was the one. I only had to know if I wanted to spend more time with her. A series of 60% sure steps culminated in our marriage.

It’s worth mentioning here that there’s a difference between knowledge and knowing. No matter how many books we read or experts we consult, we must still act to know something for ourselves. And through acting, however tiny and trembling the step forward may be, we prove to ourselves that certainty is not necessary for our action, growth, or satisfaction.

No wizard is coming, and that’s okay because, like Elsa in Frozen 2, you are the one you’ve been waiting for. And like Elsa’s sister Anna, you change the plight of the platypus if you do the next right thing and the one after that.

Trap #2 - People Pleasing

The second trap for my platypus friends is people pleasing.

I’m a recovering people pleaser myself, and I recently interviewed two other mid-career creatives with the same tendency. In their cases, an unexpected pregnancy and a lawsuit revealed what had long been true—a compulsive desire to keep other people happy was the root cause of problems in their businesses and lives.

Many of us start service businesses because we have the required skills, we want to serve, and we’re good at it. The trouble starts when we can’t separate being liked by clients and collaborators from truly serving them. Managing their current feelings about us consumes our attention, to the detriment of the project and the health of the relationship long term.

There’s just no pleasing some people, and some of the people I have displeased were immature, unreasonable people who said unfair things, because that’s what they do.

Yet, when my sense of self-worth was tangled up with their approval and good opinion of me, I believed them. Their poor opinion of me—or even the anticipation of it!—shook my belief in my abilities, value, and long-term prospects.

The anger came later when I emerged from the toxic cloud, saw a more complete picture of the situation, and recognized that the other party had misrepresented it in a way that served them.

Why hadn’t I seen what was happening?

I tried to make it so that everyone would speak well of me, and that fool’s errand lowered my self-respect, lengthened my recovery time, and delayed my progress. Jesus himself said, “Woe to you, when all people speak well of you” (Luke 6:26 ESV).

People pleasing starts out as a snack machine that spits out rewards and snacks. Who doesn’t love praise and a bag of Doritos?

It turns into a trap because it gives us a distorted view of ourselves, our service to other people, events, and the part we played in them.

Ironically, people pleasing poisons relationships. The better you are at it, the more energy you put into it. The more energy you put into it, the further you get from the real prizes of a deep belief in your belovedness apart from your performance, results, or people’s opinion of you and intimate knowledge of your will, desires, and dreams.

I have found the inverse to people pleasing to be helpful. When I am living well, I will inevitably displease some people, and my willingness to be disliked gives me a clear and continuous advantage in my work and business. Yesmen are a dime a dozen, but nomen—nofolk?—are rare and valuable as friends and advisors.

Not everyone is going to love or even like us. Once we embrace the discomfort of that, we find it easier to know what we really want.

Trap #3 - Comparison

The third trap for multipotentialites wanting to reinvent themselves is a more familiar one that I mentioned at the beginning, comparison.

My friend Lauren comes to mind here because she is, in many respects, my platypus opposite, the Golden Retriever. Lauren and I were two of the “smart kids” in high school and study buddies. Lauren always wanted to be a veterinarian. I had no clue what I wanted to be. I knew I liked writing and making people laugh. I was protective of my time. Therefore, my career path was… [inconclusive].

Fast forward twenty-five years from our graduation, and Lauren owns a successful vet practice in an affluent neighborhood. My parents take their horrible cat Ellie there, and I have no doubt they pay a pretty penny to medicate Ellie who pulls out her own fur and pees in their foyer.

My work isn’t intelligible the way “vet practice” is. My many fascinations have commonalities and coherency, but compared to Lauren’s, my career looks like I got lost at a county fair: freelance writer to lean agency founder to iOS developer to tech startup cofounder to children’s book author to branding and marketing studio co-owner to online course creator to business coach to strategist to business nonfiction author to retreat facilitator to paid speaker to online community leader. I tell jokes and am great at parties. Hire me now.

I haven’t been idle obviously, but if I were to set my trophy case of modest entrepreneurial successes alongside Lauren’s vet practice, income, 401k, health insurance, house, pool, car, weekly massage, fancy groceries, and vacations, then I might start to think something is wrong with me.

While assuming that Lauren’s life is smooth and luxurious as Wagyu butter, I might minimize or forget what I have accomplished.

I might look back at young Austin, bursting with potential, and mistakenly believe that I am wasting his one wild and precious life.

Comparison bleaches the bright colors of joy from our work and pursuits, and that loss is even sadder when you consider that you don’t really know the true contents, challenges, and compromises of the other people’s lives. Maybe Lauren is tired of being a vet. Maybe she feels suffocated by her schedule. Maybe she’d give both pinky toes and one nostril to spend hours each week writing on her back porch the way I do.

Comparison is writing fiction. We allow a fiction to cause us to believe that we missed our chance, that we are lost, and that it is too late to go a different direction.

The stories of many entrepreneurs, artists, and luminaries who didn’t start the thing that would make them famous until later in life testify that we aren’t as far behind as we think. Maybe we’re right on time.

If you want to pivot, you can.

Just remember that the pivot that sticks will be the one that honors and works with who you are and the ways you prefer to show up in the world. Remember also that, even if you get it right, you may want to pivot again.

Speaking of pivots, let’s talk about tradeoffs and tools. You can’t keep all your pet projects and ventures and have extraordinary success with one of them and work reasonable hours and love your life. You have to pick your tradeoffs.

These six tools have enabled me to gain clarity and test new directions without putting pressure on myself to go all in.

1. The Magic Word
2. Timeboxing (i.e., Expiration Dates or Semesters)
3. Experiment Framing
4. Career Portfolio
5. Groundhog Day
6. Clean Values

Tool #1 - The Magic Word

The subconscious belief among platypuses is that there is The Thing that they ought to be pursuing. This belief causes suffering even if it doesn’t cause physical pain.

We’re so itchy with the prospect of finding The Thing that we worry about missing it, like a ship leaving a dock, and we will drop what we’re doing as soon as a possibly better option pulls into the harbor.

We bounce from one thing to the next thing hoping to find The Thing, and if we don’t curb this impulse, then we end up with a curiosity cabinet full of half-finished passion projects, half-launched business ideas, and assorted ceramic frogs painted in the avant garde style of Half-Committed.

This hummingbird impulse causes regret. Anything we do halfway doesn’t bring the satisfaction of a wholehearted commitment. More on commitments at the end.

Plus, the underlying restlessness prevents us from fully appreciating the good things and good work we do have.

What helped me focus and have fewer regrets was admitting to myself that The Thing might not exist. A better bet was making a wholehearted commitment to the next thing for a period of time.

“Next” is the magic word that helps us pick one good option and ignore the many others—if only for a little while. “Next” points our own changeable hearts in a single direction that we can easily explain to ourselves. “Next” shrinks the mystery of the future to a concrete stepping stone.

I used the magic word before I started my online community in November 2024. About two years prior, I told a friend, “I have no desire to manage a community.” I meant it, then time passed. A cohort of group coaching clients asked me to keep the cohort going. They described what they wanted. That sounded suspiciously like a community to me.

“I’ll try it for six months,” I said, “but I’m not making any promises after that.”

Eighteen months later, the community is still growing.

Do I still sometimes wish that I had a plan for my life that was more like a blueprint for a castle than a curvy line of stepping stones? Yes. And wouldn’t it be nice to see the next twenty or thirty stepping stones all at once instead of just one or two? Yes. But that’s just not how my life has unfolded or how my wayfinding has worked.

I have needed the magic word, and if you need it too, then answer these four questions as honestly as you can:

• What do I want next?
• Or, what would I regret not trying?
• What is the next concrete stepping stone?
• What would wholehearted commitment look like?

You can pick the next thing without knowing what you want forever.

Tool #2 - Timeboxing (i.e., Expiration Dates or Semesters)

Many of us aren’t ready to go all in on a six-month commitment, let alone three years. As the time horizon stretches out, our anxiety goes up.

I find it easier to pick the next thing if I give the commitment an expiration date, and thinking in terms of a semester, or three months, has helped me release any hidden pressure to turn the next thing into The Thing.

I can tolerate nearly anything for ninety days, so it’s okay if I end up disliking the next thing.

Ninety days also gives me enough time to learn and accomplish something measurable. College courses count as credit hours toward degrees.

And if we stick with the next thing long enough, we gain what Cal Newport, the author of So Good They Can’t Ignore You, calls “career capital.” Commitments with expiration dates give us new skills, experience, and competencies, which in turn bring new clarity, direction, career capital, and opportunities.

Here are some of my commitments that became capital:

• Commitment: Investing in Mike Pacchione’s Speech Club, a group coaching program for public speaking
• → Capital: Knowing how to put together a memorable speech and more confidence and comfort as I deliver it in a way I’m proud of afterward
• Commitment: Optimizing my friend Mark’s Etsy shop
• → Capital: Getting paid to see if this is a direction I want to pursue with consulting or even a lean agency
• Commitment: Publishing every weekday on LinkedIn for several years*
• → Capital: Becoming a better writer and building an audience
• *Worth noting is that I kept extending this commitment.
• Commitment: Creating and delivering a group coaching program, Business Redesign
• → Capital: Testing this business model which also forced me to better define the outcome and create the playbooks that made it possible
• Commitment: Investing in Krista Miller’s Launch with a Summit Accelerator, a group coaching program for hosting virtual summits
• → Testing a virtual summit as a marketing vehicle for audience growth and profitable launches and grossing over $42,000

Did any of these things become The Thing? No. But public speaking, Etsy optimization, writing, group coaching, and virtual summits are all things I can do confidently now.

I could write a much longer essay about how each of these commitments has expanded the surface area of good things that can happen. I’ll share one specific example: The same year that I did Mike’s Speech Club, a single speaking engagement netted me five figures, a trip to Australia with my wife, and several new friendships and collaborations.

I’m not sure that speaking is The Thing, but I sure am glad I didn’t wait for more certainty before committing to improve at it.

Take out your journal and ask yourself three questions with all the honesty you can muster:

• Can you think of anything you’d like to do but haven’t started because you left the commitment big and open-ended?
• Or can you think of something that interests you and would be valuable to learn even if you don’t end up doing it all the time?
• What might a semester of that look like? What is one measurable outcome you could reasonably see by the end? For example, the outcome of that Speech Club program that I joined was giving a 30-minute talk I was proud of.

Platypuses don’t have to know where we’ll end up before we make commitments. Even our temporary commitments can have permanent value.

Tool #3 - Experiment Framing

Experiment framing is nothing new. Anne-Laure Le Cunff explored the idea at length in her book, Tiny Experiments, and if you read Benjamin Franklin’s Autobiography, you’ll find that America’s favorite polymath was running experiments to improve his virtues, habits, and routines as far back as 1700s.

Experiment framing for the next thing I want to try has helped me in three ways:

• Limited time horizon
• Sampling
• Better “data”

The word “experiment” implies a limited time horizon, and as I mentioned, I find it easier to make a wholehearted commitment if I give it an expiration date.

Being a chronically fascinated person, I know that I may change my mind later. The impermanence of experiments sends a message to my weird brain: “Relax. The stakes are low. You don’t have to know if you want this forever. You just need to finish the experiment.”

I keep returning to that idea of high and low stakes and betting because my mind constantly tries to convince me that the stakes are higher than they are.

I feel this pressure, as though I must know, I must have certainty, I must commit indefinitely.

None of that pressure or mental rubbish is real, and experiment framing helps me to push it all aside, knowing that the goal of an experiment is to sample this new thing, not find The Thing.

Sampling is important for me because past experience has shown me that I misjudge how much I will like or dislike something. I expected to like leading the Freelance Cake Community less than I have. I expected to enjoy being a fractional CMO more than I did. I can speculate, but I simply cannot know what something is really like until I try it.

My coaching clients and community members fall into the same trap as they agonize over whether to try a new type of work, offer, or niche. With all of the anxiety they bring to a change that is still theoretical, you would think someone was forcing them to get Mickey Mouse face tattoo in fifteen minutes.

I reassure them that, unlike the tattoo, most decisions are easily reversible, and that, before they reach any sweeping conclusions, they should use experiment framing as they try the new thing once and see if they like it:

• If you think you’d like to be a fiction editor, don’t think about the next decade. Instead, convince one novelist to pay you to edit her latest manuscript. See if you like it enough to edit a second novel.
• If you think you’d like to pivot your content writing business to coaching, don’t start a coaching business. Craft a one-page coaching offer in a GDoc and put it in front of ten people. Coach one paying client for three months, then reassess.
• If you think you want a big email list, don’t launch a newsletter. Commit instead to writing one email. Text, email, or message one hundred people who already know, like, and trust you—or at least you think they do—and ask if you can send them a piece you wrote that you think they’ll enjoy. Send the first newsletter. Repeat eleven more times. Then, reassess.

You may discover that you hate editing fiction, coaching, or sending a regular newsletter.

Part of you knows you may change your mind later about the new thing, and that is the part of you that digs in your heels and creates resistance before you have even started.

So if you want to get stuck less often, pretend The Thing and the certainty wizard on the white horse don’t exist and let your curiosity lead you into framing the next experiment.

Then, you let your enjoyment tell you whether to recommit after the first experiment.

It’s worth mentioning that you can sample new things in a way that doesn’t make you smarter or give you career capital.

That’s how experiment framing differs from a loosey-goosey approach to trying a new thing. Scientists design experiments. They form a hypothesis. They identify variables in advance. They pick a control. They run the experiment and measure the results. They compare the results to what they expected to happen, what they expected to learn.

Scientists bring a sharp intention and deliberate acts of observation to what otherwise might be a whim, gut feeling, or intuition.

It’s fine to use your intuition to get you moving as long as you recognize the problem that Daniel Kahneman, the late Nobel Prize-winning behavioral economist, points out:

“The problem with our intuitions, one of the many problems with our intuitions, is they come too fast. We form impressions very, very quickly, and then we tend to confirm them.” (source)

When we’re walking into the unknown, Kahneman recommends “disciplined intuition”—that is, a structured, disciplined approach to evaluating the pieces of a problem or possibility one at a time, poking at your assumptions and impressions, and extracting the maximum amount of insight.

We have better judgment and make better decisions after any experiment if we’ve done that.

So take out your journal and frame your next experiment:

• What is my hypothesis? What do I expect to happen? What do I expect to learn?
• What do I think this experiment will give me that I don’t already have?
• What story do I want to be able to tell afterward?
• How will I know if this experiment is successful?
• What question am I trying to answer?

Instead of the next thing happening to you, you happen to it, and because you proactively decide what you will measure and what data you must collect, you have more true intelligence and data at the end of any experiment. You have more clarity and confidence about the next experiment you will perform. You imposed discipline on your intuition.

Tool #4 - Career Portfolio

Most of us won’t have a career path like a single train on a rail spanning fifty years. The very idea of doing the same work for fifty years may sound horrifying and claustrophobic, even if it works for Golden Retrievers.

If platypuses don’t have a career path, what do we have? A career portfolio.

You build your portfolio by using the magic word to decide what you want to do next and running experiments with expiration dates.

One of my former coaching clients, Rachel Bicha, thought she might like creating and sending a monthly print newsletter. She chose to “pick the smallest possible idea to try first” and “keep expectations light.” She got started without having to carry a heavy psychic load. (source)

Now a year has passed, and the newsletter has become a regular project that has won a place in Rachel’s career portfolio. She can point to twelve one-of-a-kind newsletters, and feel a sense of pride. That stack of newsletters also gives her authority when she talks to a potential client about their direct mail piece or print project.

Many platypuses like Rachel don’t have a straightforward resume to show for their work experience. They have a portfolio rich with projects, ventures, and accomplishments. They have proof of their commitments and stories to tell.

It may be harder to explain at times, but it opens more options and opportunities for you.

To the right future collaborators, your career portfolio will be more interesting, attractive, and persuasive than a traditional resume.

Here are some of the projects in my career portfolio:

• Graduating with my Master’s degree in Literature with a focus in creative writing and publishing my poems in literary journals
• Developing and eventually selling a portfolio of 30+ iOS and Android apps (Bright Newt)
• Completing a Nanowrimo challenge (writing 50,000+ words of a novel in a month)
• Cofounding a business training library of high-quality videos for freelancers (Kicktastic)
• Cofounding, raising money for, and attempting to scale a tech startup (Closeup.fm)
• Creating and teaching a travel hacking workshop
• Writing a guide on improving your credit in 30 days
• Hosting 9 retreats for entrepreneurs (SPACE Retreat)
• Speaking at TEDx, Pecha Kucha, and various conferences
• Creating and selling physical time management cards (FoFi)
• Hosting a virtual summit (Fix Your Pricing Masterclass for Freelancers)
• Co-founding a branding and marketing studio (Balernum)
• Productizing a one-on-one business coaching engagement for freelancers
• Creating and launching a business-focused course for freelancers (Freelance Cake)
• Creating various other programs, products, and smaller courses for freelancers (e.g., Morning Marketing Habit)
• Leading a private, paid community for advanced freelancers (Freelance Cake Community)
• Starting and growing a weekly email newsletter (Freelance Cake)
• Launching a podcast (Freelance Cake)
• Publishing a children’s picture book (Grabbling)
• Publishing a pricing and money mindset guide for freelancers (Free Money)

I finished each of these commitments in a meaningful way, and now I can point to a career portfolio and say to myself, if no one else, “Here’s what I’ve been doing with my life.”

Here are some questions to help you build your career portfolio:

• What passion project is worth finishing even if it never makes you money?
• What skills and competencies will be more valuable in the future?
• What commitment will help you develop one of them?
• What will you finish now to minimize regret later?

You may not know The Thing, but you can finish a bunch of different things. Through finishing you can learn how to do many things. You can be proud of what you have accomplished in your life and work, even if your career isn’t as easy to understand as running a veterinary practice or climbing the ranks in a corporation.

Tool #5 - Groundhog Day

Like the human race at large, platypuses want to get what we want, but what we want changes.

On any given day, it can be hard for us to define “success” and articulate what we are optimizing for. Control over our calendars? Autonomy over our work and livelihood? Higher income? Delight in the creative process? Intimate relationships? Health?

I’ll take one of each. Thank you.

Goals dance around our heads like butterflies, and that kaleidoscope only adds to the fundamental distraction and second-guessing problem. Goal fatigue is real.

So I’ll offer an alternative to that least helpful of words, success, and to goals that may be difficult to catch and quantify. Your good day repeated. Your Groundhog Day.

You generally know what your good day contains and feels like, right?

As Atomic Habits author James Clear noted, a good day repeated can become a metric for how well you’re doing with your work and life:

“I do think there can be a simple philosophy that you can carry around. Just have one good day. Just have one good day, then repeat it.” (source)

Human beings invented philosophy to help us understand what a good life is, and because we’re brilliant at overcomplicating things—which explains the existence of baseball and U.S. tax law—I want to get annoyingly specific about what a good day and good life is, using some first principles thinking:

• A life consists of days.
• Therefore, a good life is a collection of good days.
• Different individuals prefer to spend their days, or about sixteen waking hours, in different ways, so the definition of a good day varies from person to person.
• Some uses of sixteen hours we enjoy, and they make our lives qualitatively better.
• Other uses of our time we enjoy, but they make our lives qualitatively worse. We ignore these negative effects for any number of reasons, from a sense of duty to apathy to addiction to confusion to fear.
• Other uses of our time we don’t enjoy, but they make our lives qualitatively better. We ignore these positive effects for any number of reasons, from laziness to forgetfulness to poor planning to ignorance.

So if we want good days, then we must deliberately spend our time on things we enjoy that benefit us and things we don’t enjoy that benefit us while we reduce the time we spend on things that we enjoy but that make our lives qualitatively worse. When we put together enough good days, we end up with a good life.

That last paragraph may read like a bowl of oatmeal, but how often do we nurse dissatisfaction with our lives while also failing to change the makeup of their basic building blocks, our days?

You’ve surely heard the parable about the American executive who tries to persuade his Mexican fishing guide to build a fleet and business empire in order to get the simple life that the guide already had, one spent fishing, playing music, and enjoying his family.

There’s a near-universal temptation, at least in the Western hemisphere, to fall into this trap. We climb the ladder only to end up where we started.

We work hard to create a sense of abundance, security, and significance that was always available to us if only we paused to glance around. Do I really want a new car or do I want to invite old friends over for barbecue and stay up late talking?

Consider my several “bad” months of revenue in 2024 and 2025 when I still managed to pay my family’s bills. While we barely broke even, I spent less time on billable work and more time writing.

If a good day repeated had been my primary metric, then I would have seen those months of lower earning as remarkably good. Apart from bank accounts or other vanity metrics, I know I’m succeeding (or whatever) if I’m stringing together more and more days that do not include nonstop meetings, big egos, corporate politicking, and bureaucratic red tape; and days that do include various spiritual practices like prayer and reading scripture, exercise, eating healthy foods, reading, writing about what fascinates me, unhurried time with my family, and coffee with a friend. I already know what my Groundhog Day contains.

I am referring to the classic 1993 Bill Murray movie “Groundhog Day.” Murray plays Phil Connors, an arrogant, self-centered TV weatherman who keeps waking up on February 2 in Punxsutawney and repeating the same unpleasant day until he decides to use the loop to improve himself and help others.

When you have no other clarity to speak of, your Groundhog Day will guide you:

• What does the container of a good day hold for you?
• If money were no object, how would you spend your time? How would you spend your freedom? Take some time and describe what a satisfying day looks like for you.
• Will the path, pivot, or transition that you’re considering give you more days spent on those pleasures, people, pursuits, and beneficial discomforts and challenges?
• Will it take you there directly or is it roundabout?

As you think about where to go next with your work, optimize for days, not dollars.

Tool #6 - Clean Values

The word “values” is similar to the word “success.” We use it so much that it has lost its meaning. Rather than reach for a dictionary, I’ll make up my own definition: Values are the invisible principles and preferences that make us pick one option over another.

If predictability, safety, and comfort matter a great deal to Sally, then she will take on a big, high-paying project she doesn’t find all that interesting for a company she doesn’t believe in. Her values sent her that direction.

Sade may take on a smaller project with an apparel brand. It doesn’t pay as well, but she cares about sustainability, equity, and doing design work she’s proud to share. Different values, different direction.

Values are like fuel that we burn. If your fuel is dirty, then you will experience less peace and contentment. No matter what you achieve in your life, you will enjoy it less.

Entrepreneur and investor Brent Beshore was the first person I heard talk about “dirty fuel”:

“The world loves my false self. The world loves that fear-driven self. I can get an extraordinarily incredible amount done. A friend of mine calls it clean fuel versus dirty fuel. It’s very difficult to see. The car looks like the car from the outside. Very difficult to understand. Is it clean fuel or dirty fuel that’s operating the car? And I mean, that car can go fast. It can take a lot of people with it if I’m on dirty fuel. And in some ways dirty fuel is a more potent fuel in the short term for me. I get more stuff done quicker, and even sometimes with higher excellence, out of dirty fuel than I do with clean fuel. That fear is a heck of a motivator.”

Beshore goes on to point out the problems with dirty fuel:

“The problem is that it’s [dirty fuel] got all kinds of contaminants in it and you eventually torch yourself, and the car breaks down and you go off the rails and blow yourself up—whatever analogy you want to use. So getting back to the original question, What’s changed? I think that more and more, I’m trying to operate on clean fuel. I’m trying to be self-unconcerned. I’m trying to become an elder.”  (source)

My fuel has often been dirty. My wife would tell you that I have trouble sitting still—that is, not working—and if you asked me why I struggled to slow down, ignore my to-do list, and relax, I would have concocted a bogus answer about how my work and hobbies overlap.

The full truth was that my relationship with work was complicated and that I hadn’t taken the time to pull it apart and understand the ingredients in my fuel.

On the one hand, I worked because I wanted to do good. I wanted a better, more equitable world. I wanted to give people a hand up because I have suffered less and had more advantages than many.

I liked seeing my effort become concrete results. One of my early hospitality clients increased bookings 198% year over year. Another client, a prosthodontist, told me that his patients and colleagues loved the copywriting I had done. I liked knowing that my work had a positive impact on others.

I worked because I wanted better for myself and my family. I want my kids to have plenty of opportunities: You want dance lessons? Go for it, darling. I worked because I wanted more beauty and poignance in my life, more bedazzled moments.

On the other hand, I worked because I was afraid of what would happen if I didn’t.

I worked because I experienced betrayal, rejection, and profound loneliness in middle school, and without knowing it, I made a compact to achieve and achieve until no one could deny my worth, make me feel ashamed, or push me to the outside. Achievements would prove that I deserved love, respect, and belonging—a seat at the Cool Kids Table.

What was the result? I always had to be achieving something.

Work was camouflage and armor and anxiety made manifest. I worked to meet external measures of success not because they mattered deeply to me but because I was afraid of what people might think or say if they found out that I had quite ordinary problems.

I worked because my bank balances embarrassed me and because my family’s finances felt fragile. What would happen if we came up short too many months? I white-knuckled my calendar and to-do list to convince myself that I had more control over my life than I really did and burned out hard in 2015 and 2016.

Work was a hiding place and distraction from deeper questions. I often felt powerless to do something about the bigger problems in the world, and I couldn’t do much improve my wife’s health. People have always told me that I had great potential. Did my life reflect that potential, or had I wasted it? I didn’t love myself fully. I didn’t accept myself.

What was the result? I worked more than I wanted to, more than was good for me, in an attempt to silence the voice in my head saying, “You aren’t doing enough. You aren’t enough.”

Work was salvation. I worried that things would always be this way, that I would always feel like I was one bank deposit away from obvious failure, ridicule, and rejection. My life felt messy and chaotic, but here was one thing I could point at and believe I was doing well. “The rest of the house is a disaster, but the kitchen is clean.”

What was the result? I became too efficient, which meant not spending time on other things that nourish me. Fly fishing. Friendship. Poetry. Playing with my kids. Rest.

I worked too much to temper my disappointment in my compromises, my frailty, my limits, my smallness, my humanness.

Inside of me were two boys, one boy looking at the sky and dreaming and another with his innocence crushed like a flower under reality’s heel. Part of my journey has been welcoming both of those boys into my center, fully accepting how they helped me get to where I am, and soothing them the way I would my own children, “It’s okay to rest. You are cherished. Like the birds of the air, your needs will be taken care of. Trust God.”

If the main ingredient in dirty fuel is fear, then clean fuel must contain fear’s opposite, love. Love drives out fear. USC philosophy professor and theologian Dallas Willard put it this way:

“Love focuses on the promotion of what is good, and if you love a particular thing, then you focus on the particular good of that thing.” (source)

Love is clean fuel, a clean value, and when I’m feeling stuck, confused, or discouraged, I now know to ask, “What do I love?” I’ll ask myself yet again. “What is good for that person or thing? What am I capable of today?”

Here are other clean values that drive me: curiosity, enthusiasm, kindness even in the face of anger or spite, generosity, making beautiful things, relationships over incremental profits, joy as a posture and practice, and full presence in the vein of Jim Eliot: “Wherever you are, be all the way there.”

I doubt that our values will ever been completely clean. Moving toward love, curiosity, kindness, and joy will be a lifelong journey.

The sooner we examine our deepest motivations in our work, the sooner we know what type of fuel we burn most often—and the sooner we begin to separate our identity and sense of significance from anything we do or don’t accomplish.

This is how we have more peace, and this is how we redeem work.

So what drives you? And what type of fuel do you want in your tank?

These questions can help you find your way forward:

• What non-negotiables or guiding principles determine how you show up in the world and do business? What will you never do?
• What can you not imagine not still being true 10 years from now?
• What are you not willing to compromise on even if it means losing in the short term in business?
• What would go on the motivational poster on your wall, even if it seems cheesy to other people?
• What do you love for its own sake? Is my work promoting what I love?
• Beyond making money to pay bills, why do you work? What makes good work “good” in your mind?
• When you aren’t working toward a specific goal, what musts, oughts, and shoulds influence decisions and actions? What loves are etched in your bones?
• Which criteria and conditions in your business will leave you with the least regrets? What is required for you to do business with a clear conscience?
• What are you not willing to sacrifice under any condition? For example, I want to be the dad who's around so much that his kids complain about it to their friends. And I want to keep my marriage. And I want to protect the basic dignity of people I meet and do business with.

Our work and our businesses have a way of tying us up into knots and putting our heads on backwards. Ambition doesn’t heal inner wounds any more than money buys intimacy. Occasionally, we need our values to straighten us out and point us in the right direction.

Closing Thoughts (or, make clear commitments)

I’ve got some bad news: You may never know what you want to do with your life, and you still have to live it.

I’ve also got some good news: You may never know what you want to do with your life, and you can still live a beautiful life.

Uncertainty makes us feel fragile, and yet uncertainty traces the beauty of the human condition. We do not know and cannot know what will happen, tonight, tomorrow, or ten months from now, and this is true for platypuses and for Golden Retrievers, no matter how certain they may be about the path they’re on.

One bad knock on the head, and all of a sudden, you can’t do the work that defined your identity and fed your certainty.

Certainty is the racket we’re all participating in to varying degrees, and there’s nothing inherently wrong about wanting to feel more certain. Getting more intel and hardening it to insight is what wise people do. Wisdom is experience distilled to truth and made shareable.

However, we’ve got to choose and act even when we don’t feel wise, and that leads me to the remedy for uncertainty, which is commitment. Jim Dethmer, founder of The Conscious Leadership Group, talks about how we’re always 100% committed:

“Everyone is already fully committed. You can’t get more committed. Telling yourself or others to get more committed is a waste of time. The key is not more commitment, it’s clear commitment.”

Clear commitment means you don’t have one metaphorical foot out the door. Clear commitment means you’re all in for a certain amount of time.

In a way, the other six tools are the conditions for clear commitment. Use the magic word, next, to pick your next pivot or change in focus or direction, without knowing what you want forever. Timebox the choice with an expiration date. A single semester is fine to start with.

Use experiment framing to bring sharp intention and deliberate acts of observation to what otherwise might be a rather vague detour.

Think about how the results of the experiment can fit into your career portfolio and help you have more of the kind of day you want to repeat, your Groundhog Day.

And reconnect with your clean values so that the fuel that drives you isn’t contaminating your work and life but producing the good you intended.

If you remove any of those conditions, it’s much harder to make a clear commitment.

And if you’re confident that a new commitment meets those conditions, then your mind can relax into it, and you won’t be plagued by the self-doubt and second-guessing that grows up around unclear commitments.

You’re already 100% committed to the path you’re on, so if you want to take your work or your business a new direction, then take the time now to renegotiate the commitments you already have. Free up some attention and give it to your next experiment.

Above all, we must be honest with ourselves. We all know people who don’t do much of anything, and they try to convince themselves and us that caution and good sense are driving them. The truth is, they’re afraid—afraid to make mistakes, afraid to be ridiculed and rejected, afraid to find out they are wrong in their thoughts and choices, afraid to discover that the very people they criticized had the right of it, afraid of the grief caused by time wasted not on failures but on a purely theoretical pursuit of wisdom, growth, and excellence.

I still find fear in my fuel. You will too. The trick of growth is naming it faster and doing the next thing scared.

There is no courage without fear. There is no progress without mistakes. There is no change without pain. There is no certainty, only a more or less convincing illusion of it. There is only acting despite the fear.

The only choice that life’s mystery leaves us is believing. We act on faith, or we don’t act at all.