Introduction

My Journey from Full Time to Free Time

There is no way to happiness, happiness is the way.
—Thich Nhat Hanh

It is one p.m. on a Tuesday, and I am glued to the couch, procrasti-eating so that I don’t have to tackle the one thing I promised myself I would that day: Email Everest. As I polish off a pint of Ben & Jerry’s Strawberry Cheesecake ice cream, a fellow business owner texts:

“Do you ever have the feeling of just wanting to burn it all down?” she asks with a laugh-cry emoji.

Why yes! Yes I do . . .

“Funny you mention it! I’m at Hooky Headquarters as we speak,” I reply, “glued to the couch eating ice cream. I can’t seem to move or motivate myself to do anything at all.”

When invoked, burn-it-all-down mode (BIADM) means we have reached a point of weariness, burnout, frustration, or dread in our business, and we wonder (fantasize!) whether instead of pressing ahead in our chosen field we should just burn it all down and pivot into real estate.

Or fill in a vastly different fantasy alternative career of your choice, one that probably isn’t any easier in actual reality.

I have had many burn-it-all-down moments in business: everything from complete exhaustion while launching my first book and leaving corporate life; to a petrifying plateau two years into self-employment where I didn’t have enough to cover my rent; to overwhelmed exasperation watching the majority of my projected income vanish in March 2020 when the pandemic hit.

BIADM can be a passing fantasy during a crushing week, or a crucible you endure after years of veering slightly off course, until you realize you are completely lost. You might experience moments of BIADM in response to compare-and-despair while binge-listening to business podcasts, or during an exhausting social media infinity scroll. You might hear a fellow owner express wanting to burn it all down after losing their biggest client, or even landing their dream client that in actuality becomes a bureaucratic and logistical nightmare of paper pushing, hoop jumping, and people-pleasing.

No matter when it strikes, the impulse to burn it all down is a signal flare. When you are stranded on burnout island, your body and your business start sending distress signals. These torching fantasies are a sign you are not working sustainably. Something is off, whether your schedule, your projects, your margins, your clients, your day-to-day work, your team, your delegation, or a mix of all of the above.

These moments are also ripe for our biggest business breakthroughs. I will share a few of mine in a moment—the ones that inspired this book—but first, the breaking points.

⚙️ Business Stress Is a Systems Problem

Stress is a systems problem.

Not all stress, as there are terrible evils in the world and crooked societal systems wreaking havoc on people and planet. In the context of this book, however, many of the stresses of running a small business can be attributed to broken—or nonexistent—business systems.

It took me years to recognize this because stress often arrives mixed with success, and I had achieved successes that surpassed my wildest imagination. Still, they added complexity and raised the stakes higher. I knew the saying, “All business owners experience problems, just with more or fewer zeroes at the end,” but I also knew there had to be a more systematic way to tackle these challenges so they would not reoccur.

I was accustomed to riding a rollercoaster of career highs and lows in high-pressure, fast-paced environments. Early in my career, that was my default way of working. Having built businesses throughout my childhood, I was used to being a time task-master and requiring more, more, more of myself. At fourteen years old, I developed a compulsive disorder called trichotillomania. Like nail-biting, when stressed I literally pull my hair out, something I still struggle with today.

I also developed a deep desire to serve others by reducing their anxiety, because mine was so overwhelming. Perhaps because I saw how hard my parents were working to pay the bills, I strove to do whatever I could to free them and others from what I perceived—at least, as a child—as burdens. If I could make others’ lives easier, maybe I wouldn’t be a burden either.

Partly as a coping mechanism and partly out of intrinsic joy, creating order out of chaos has always soothed me. I love tinkering behind the scenes of my business, teaching myself and others new software, voraciously gobbling up business books to smooth the path forward. I love open-sourcing my templates and solutions, from book marketing to rapid course design. One of my mugs says “I heart spreadsheets,” and I color-coded my bookshelf long before it was a trend, with books stacked up to the ceiling in my New York City apartment. I procrastinate by tinkering in my business’s operations, looking for new areas I can organize or automate.

Still, for years this mix of ambitions, combined with an unconscious effort to assuage insecurity through achievement, meant my career eyes were often bigger than my stomach. My boss at a political polling start-up, my first job out of college, often joked that I was “hiding five Jennys” in my office because of how much I juggled, a pattern that persisted in taking on too many roles in my own business years later.

While launching Google’s global Career Guru coaching program in 2011, I was also putting the finishing touches on my first book, while taking two weeks off to attend a residential yoga teacher training. By the time Life After College launched six months later, I skidded into a sabbatical for a ten-city book tour. Days after the launch, when a friend asked how I was doing over burritos at Chipotle, I burst into tears. I was a frazzled mess. Clear that I could not juggle my side hustle and full-time job any longer, I gave my two weeks’ notice to Google that summer.

In those first two years of self-employment, I was the only one working in my business. Everything hinged on me. When I needed to take a step back to rest, or to envision the next phase of my work, my income ground to a screeching halt. As an empath, introvert, and what psychologist Elaine Aron calls a “highly sensitive person,” it was too much stress for my system. When running your own business, there is no reward for doing all of the jobs, other than burnout. I had to learn that the hard way, as so many of us do.

So I committed to building a better, more blissful business. One that would be heart based, systems focused, delightfully tiny, and fun. I strove to eliminate preventable stress—as much as I could, anyway.

I vowed to launch my second book, Pivot, with greater scale in mind. I sought the opposite life of that of an influencer. I resolutely did not want people to follow my work because of my looks, my lifestyle, or my ability to churn out ceaseless content, but for my bigger ideas. Soon, I stopped participating in social media altogether—a huge relief. No more keeping up with the infinite stream of content and comments, always feeling behind. By taking the focus off me at the center of my business, I could spotlight the programs and their value instead.

By the time Pivot launched in 2016, I was prepared with scalable streams of income. I trained a small group of people to meet the increased demand for one-on-one career coaching services, and eventually stopped doing one-on-one coaching myself. I built scalable corporate programs, launched a podcast that quickly became my favorite creative outlet, and streamlined my systems. I finally invested in “going pro” with software services to realize

their full functionality, instead of squeezing everything I could out of their freemium editions.

Creating this space helped me land train-the-trainer (TTT) and intellectual property (IP) licensing deals with several dream corporate clients who implemented Pivot programs globally, helping me pull in nearly $700,000 in revenue the following year, a figure I barely believed when looking at my balance sheet. Freedom-lover that I am, I did this without any full-time employees—including me—as I was working ten- to twenty-hour weeks on average. This time, I was not the bottleneck to Pivot making its way into the world. So long as I released my grip on things being “perfect” without me, I could teach others how to deliver the material. Companies around the world could open-source it and teach in their own language, with their own context and internal examples.

When you run your own company, “hard” work no longer has a direct correlation to the profit you generate. In the entrepreneurial realm, time is decoupled from money. There is no guarantee that pouring more time into your business will yield positive results.

In a small business, there is no place to hide. Hard work itself is meaningless. The work must work—it must be strategic and revenue-generating, or you will quickly go out of business, like I almost did.

📬 The Check Is in the Mail

Every one of my biggest business dips required imagining a new way forward, saying no to good opportunities, people, and pricing that no longer resonated. Each one sparked conversations with my team to clarify our priorities, increase our systems sophistication, and refocus on our strengths to serve the business best.

Even still, with all the progress I made on staying small while creating scalable programs, one of my biggest burn-it-all-down moments came three years after Pivot launched. Let’s call it the seven-year business itch, a time where once again I was juggling too much, personally and professionally. I got married, bought a condo in New York City, and started attending Union Theological Seminary to “put myself in the path of pivot” of new people and ideas, studying the intersection of spirituality and work, and the growing “spiritual but not religious” population. I was squeezing intense academic reading and essay-writing into the nooks and crannies of my time and energy, jumping into empty classrooms to conduct work meetings in between lectures.

Amidst all this, I landed an exciting corporate client that booked me for workshops internationally, with the promise of licensing the material if those pilots went well. This engagement represented a hefty chunk of my income for the next six months, which I desperately needed to help pay for school, health insurance, and the new carrying costs of an entire household.

However, their “check in the mail” took its sweet time, notching up my anxiety with every passing month it was delayed. While we had agreed on up-front payment, I started the work long before the deposit arrived, in an effort to be friendly and accommodating. Clearly, these are not the best values to lean on when negotiating corporate contracts! Negotiating was my Achilles’ heel as a recovering people-pleaser, but I hadn’t yet figured out how to delegate this aspect of my business or improve enough to get comfortable. I always had more skin in the game than the multinational companies, therefore less leverage when negotiating. I wanted their business too badly. One check could make or break my business, while the expense of hiring me was barely a blip in their budget.

The frustration of waiting month after month for the money to pay my mortgage, racking up credit card balances to swing me like Tarzan from one branch of bills to the next, all while traveling internationally delivering trainings for this client, sent me over the edge. At the time, I had a director of communications who was wearing as many hats in the business as me, and a virtual assistant. Both were ready to make their own transitions, which meant I needed to rethink my entire tiny team and how the work would flow through it.

Despite years of striving to create more distance between my business’s revenue and the time it would take me to earn it, I was back where I started in my first days as a solopreneur: stressed about money, overly reliant on one big client and one big check, and resentful at the boundaries I failed to set when negotiating the contract. Pressure weighed heavily. I still carried all the operational knowledge of how to run my business, juggling over ten streams of income that were legacies from years of experimenting.

No matter what I was delegating, the cognitive burden was still mine. It was the equivalent to one partner doing more household work than the other saying, “It’s not just that I need you to help do the laundry, it’s that I need you to help notice when the laundry needs to be done in the first place.” In many cases, it wasn’t that my team did not pull their weight on purpose, just that they didn’t realize what needed to be done from a more strategic, forward-looking vantage point. I was stuck delegating tasks, when what I really needed was for team members to own their larger roles, including project outcomes and results.

Again I fantasized about winning the lottery or burning it all down, whichever came first. Alas, I still knew deep down that I never wanted to work for someone else, if I could help it.

So I gave myself permission to hit pause. I took leave from seminary school, stopped taking on new coaching clients, and I suspended publishing the podcast and my newsletter for six months. Once again, I vowed to rebuild, even better this time.

I started restructuring my business systems from the inside out, with clearly articulated operating principles so my team knew the logic of why and how I did things, a Manager Manual with full documentation on how to run every aspect of the business, and I expanded into what I call a Delightfully Tiny Team of three part-time people, four including me. Thank goodness I made those changes. What I dubbed “Jenny Blake Enterprises (JBE) 3.0,” my business renaissance, occurred in the summer of 2019. In less than a year it would all be put to the test.

When the pandemic hit seven months later, I had unknowingly prepared by making these operational shifts. Six-figure contracts overdue to be signed were wiped off the table, and nearly every speaking engagement was cancelled or postponed two years into the future. Miraculously, I didn’t want to burn it all down any longer. The pause in client work clarified my strengths, what income streams were no longer a fit, and how I wanted to simplify my business. It was the first time in fifteen years that I was not traveling every two weeks for work, so my creativity started to return. Because I had already restructured my team, our systems, and our offerings, I was able to keep the lights on with monthly recurring revenue from leading a private community for small business owners. We exchanged much-needed emotional support during those rocky months. I doubled-down on the podcast and published daily for three months, one way to serve my community during a crisis.

I revamped my sales process for corporate clients, and documented every step and talking point so someone else could help land new business, something I previously felt would be impossible. Now, I no longer hold sales calls, coordinate scheduling, or negotiate contracts. I leave those to specialists who can make it their focus and are willing to “be the bad guy,” leaving me to do what I do best: using my voice in a one-to-many way. Specifically, to simplify complexity through what I call ongoing public original thinking, activities such as delivering keynotes, podcasting, sending my weekly(ish) newsletter, and writing this book.

This book would not exist if I had not found a way to reduce friction and return to creative flow again. Freedom, joy, ease, surrender, and serendipity became my new guiding success metrics. Now I know, deep within my bones, how non-negotiable it is to be present in my business and life. I know what enough looks like, what is worth pursuing and what isn’t. I avoid chasing the hungry ghosts of money, fame, power, and control, what I call the Four Horsemen of the Business Ambition Apocalypse.

This anecdote, shared by Vanguard founder John C. Bogle in the opening to his book, Enough, captures my sentiments:

At a party given by a billionaire on Shelter Island, Kurt Vonnegut informs his pal, Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel Catch-22 over its whole history. Heller responds, “Yes, but I have something that he will never have . . . enough.”

❤️ Heart-Based Business

“Are you ordering off yesterday’s menu?”

This inquiry stayed with me for weeks after encountering it in a book called Beyond the Known by Paul Selig. It called attention to where I was stuck maintaining legacy programs in my business, instead of creating work based on today’s menu of new options.

Where might you be ordering off of yesterday’s business menu? Where are you making assumptions that are keeping you stuck, working on the wrong things or in the wrong way?

For Kajal Dhabalia, founder of Wholesome Soul, this question became her guiding light during a time of transition in life and work: moving, reorienting her business post-COVID, and supporting aging parents.

“Giving myself time to think about my menu—what was lingering out of habit and what was really calling me—made me realize how much I wanted to shift into well-being,” she said, after unexpectedly closing her online art and gifts store business when the pandemic hit. A graphic designer by trade, Kajal took on design work to pay the bills, while researching wellness education programs.

“All along there was this resonant option there, but I just wasn’t able to see it,” she said. “But, now as I am in the middle of getting certified, I am excited to see how all my work is coming together even stronger than I could have imagined. I just had to let go of expectations around what I should be doing, and open myself up to the wisdom within that was there to guide me all along.”

It is time to ditch yesterday’s business menu. Instead of growth at the expense of your health and peace of mind, listen to the urges to simplify, streamline, and de-stress. Perhaps you, too, value small, agile teams that provide maximum freedom and optionality. On today’s menu, you can seek just enough support to make things easier, but not so much that it becomes a burden itself, where you are struggling to earn ever-greater revenue just to feed the overhead beast. You can be thoughtful about who you seek to serve, and the impact you are making. You can work with integrity, honoring the health and humanity of all involved.

I call this operating mode Heart-Based Business. When I was leaving Google, I was so afraid of going broke, failing at business, making the wrong move. Every time those fears arose, I started countering with: but what if I earned twice as much in half the time? In later years, I added “with ease and joy” to include how I was working, and “while serving the highest good” to ensure I stayed focused on what was best for all involved.

Over the last decade this evolved to become a central guiding question for Heart-Based Business, one that I have shared with thousands of small business owners to stay focused on possibility instead of worst-case scenario outcomes. Heart-Based Business means engaging with an ongoing inquiry (feel free to create your own version with wording that resonates):

How can we earn twice as much in half the time,
with ease and joy, while serving the highest good?

As Heart-Based Business owners, we know it is not about who can hustle, grind, and grit hardest to “beat” the competition. That type of business risks burning as an uncontrolled wildfire, destroying everything in its path. Compare that to a controlled fire, one that clears old underbrush, stimulating healthy growth in a contained, strategic, and systematic way.

Consider: does your business give you energy, or does it take energy?

If the latter, is it because of short-term efforts that are strengthening you for the long-term, or are you stuck in never-ending loops with no light at the end of the tunnel? Your business might have strong systems in place, but a few broken links that need fixing. Or, you may have the wrong systems set-up for what you are trying to achieve. Perhaps you have not yet created sustainable, repeatable systems in the first place, and are relying on fatigable human systems like willpower and memory.

You deserve to honor your life while you build your business.

Call it a “lifestyle business” if you want—a term I avoid for the pejorative tone many say it with—but what is the alternative? A non-lifestyle business where you are miserable by your own making, trading your precious present moments for a future vision that might not happen? What if you die before you mint those millions? Will you regret not investing more in the “lifestyle” ingredients of meaning, community, family, and vitality?

These ingredients are at the heart of life-giving businesses. Free

Time is not about working as little as possible. Nor is it about creating a lifestyle business purely for one’s own gain. Life-giving businesses energize everyone who participates in them, from the owner to team members to clients and community.

I don’t work full time, I work free time: by repeatedly applying the principles and systems throughout this book to happily, and strategically, work less. When you run your own business, working less is often harder than working more. It requires building sophisticated systems and trusting a team to take care of smaller details.

In traditional corporate environments, “part time” conveys working only part of an expected whole (role). Let’s redefine ten- to thirty-hour weeks as the new “full” time, as these hours, filled with engaged focus, allow us to have a fuller life outside of work. Of course, you will work more when needed during passionate sprints and for important deadlines, but you will also celebrate, guilt-free, weeks where you have achieved glorious spaciousness.

As much as I believe the typical, traditional corporate work-week needs restructuring, I would not dare prescribe what that looks like for you. I do want to give you a few permission slips. There is also a blank template for these in the back of the book, ready to prescribe to yourself or a friend. Many of us know, now, that what took us far in the early years—hard work fueled by adrenaline—is not what will carry us forward*.*

Forward, in this case, is not reaching a financial threshold or chasing vanity metrics while miserable. Forward is peace, harmony, progress toward a larger mission, abundant cash flow, healthy profit, and most of all—freedom. Freedom of choice around what to work on, when, and with whom. Free from the tyranny of your worst boss (hint, look in the mirror!) haranguing you day and night about your aptitude. Free from your secondary title, Chief Everything Officer, the roadblock to progress. Or perhaps you are far past these challenges, and you want to feel even freer to follow an exciting future that beckons.

Business-building is by nature a perpetual work-in-progress, but you can break down bottlenecks and bureaucracy by putting time-freeing systems in place. Even if you are a passionate entrepreneur for whom meaning is already deeply imbued in your mission, it can be hard not to get dragged under by the riptides of maintenance and minutiae.

What would be possible if you could follow a simple process today that would free your time far into the future?

Free Time Framework

Your mind is for having ideas, not holding them.
—David Allen

Free Time is a philosophy and a framework. In the context of running your business, Free Time has a double meaning:

As a verb: The continual process of freeing your time to do your best work through smarter systems; and

As a philosophy: Reimagining how we work, optimizing for freedom and Heart-Based Business values, instead of orienting toward money or growth at the expense of time and health.

In the concluding chapter of Pivot, I say: “We will all face many more pivots on the road ahead, big and small, planned and unplanned. My aim in this book is to teach you how to teach yourself to fish—to persevere and thrive—when navigating these changes.”

When I mentioned this to my friend Charlie Gilkey, founder of Productive Flourishing and former logistics officer in the Army National Guard, he took it up a notch: “Design it so that no one has to think about catching the fish, because there’s a system for that.”

We can extend this metaphor further. Wallace Wright, author of Learn Systems Thinking, encourages an even more holistic analysis:

Systems thinking requires that we look at the bigger picture. What if there aren’t enough fish left in the water source because of climate change? What if the water is polluted from the activities of corporations or individuals? Who controls access to the lake? How does the person who is obviously hungry afford to buy the materials necessary to catch the fish? What about the opportunities for expansion? Is there a local market for extra fish? Could this be a chance for a larger and longer-term investment?

This is just one thought exercise illustrating systems principles that can improve how we think.

The Free Time Framework (FTF) is a process you can continually repeat as you move from friction to flow (more on that in the next section). Anywhere in your business that you experience friction, cycle through this process—Align, Design, Assign—to free-up time. The book is structured according to these three stages.

In Part One: Align, you will start with your mind, releasing yourself from invisible and outdated ways of working that are keeping your time unnecessarily and artificially constrained. You are your best asset, and systems are a skill. Before optimizing any project, ensure the work aligns with three key areas:

Your values: Operationalizing what makes you and company unique

Your energy: Discernment about what to work on (and how) to achieve results

Your strengths: Doubling-down on your talents, intuition, and imperfection

This stage is also an important gauge: If you discover the work or opportunity no longer aligns, you will phase it out. No need to systematize what should not be done in the first place.

In Part Two: Design, you will design smarter systems for your time, including streamlined processes for tackling work. You will become more discerning about what you work on and when, automating tasks before you have to think about delegating them. It will be impossible to truly free your time as a business owner if you work entirely alone. Your best bet is creating a lattice of support, one that complements your strengths and provides coverage for the rest.

The Design stage involves defining three key areas before delegating the work:

Ideal outcomes: How you will know when the work is complete

Desired impact: Results that these projects will achieve for your ideal audience

Process: Tackling the work in an intentional, streamlined manner

In Part Three: Assign, you will focus on working well with an agile Delightfully Tiny Team, even if no one works full-time. You will strengthen your delegation muscles to collaborate more effectively, without becoming a bottleneck for questions and approvals. You will ensure that every task is captured with a clear owner (ideally not you), that every question “lives three lives,” and that each person in your business ecosystem is clear on three key things: who will do what by when, noting the “do not pass go” checkpoints along the way.

This Free Time Framework can help you navigate strategic projects as well as tactical day-to-day annoyances, starting with a simple diagnostic inquiry: Are you in friction or in flow? Wherever you encounter excessive friction, you will apply the Align-Design-Assign process.

🌊 Friction Versus Flow

The early days of any business are inherently scrappy, doing whatever it takes to create products and services that yield consistent cash flow. For many entrepreneurs, success can breed added stress.

When investigating the root causes among clients and colleagues, three common friction points arise:

• Pressure to take on new clients to meet escalating overhead and payroll;

• Prices that are too low, not reflecting the value delivered and increasing complexity of running the business, and

• Porous boundaries with team and clients that consume crucial recharging time.

If you are currently experiencing any of these, with strategic shifts you can move your business’s operating zone from friction to flow. By identifying where you are experiencing friction in your business, in areas large and small, you can apply the strategies throughout this book to simplify and streamline, freeing up time and energy. Let’s look at both sides in more detail.

Friction: Disharmony, things are not clicking easily into place. You are experiencing resistance, procrastination, overwhelm, or even dread when contemplating next steps. Too many mistakes happen, work falls through cracks, and things start going haywire. You feel guilty, even embarrassed, by the state of your systems, and you might be questioning if your ambitions match your business strategy. Even prolonged confusion or boredom can be a form of friction: nothing is motivating you to get out of bed.

Flow: You have eliminated most busywork and are focused on the vital few projects and clients. You spend the majority of your time working on tasks that you and only you can do, aligned with your greatest strengths, while delegating the rest. Mihaly Csikszentmihalyi, author of the seminal book Flow, describes this state as effortless achievement, a deeply immersive near-ecstatic bliss, where you barely notice time passing. According to a McKinsey study, executives report being five times as productive while working in a flow state. Synchronicities abound, and you are aware and engaged enough to create what Good to Great author Jim Collins calls “return on luck.”

Where are you beset by the burdensome B’s: getting bottlenecked, bored, burned out, or buried by bureacracy? Running a business does not have to be so hard, or stressful, or overwhelming. We all go through dips along the way, sometimes on an hourly basis, sometimes daily, sometimes seasonally. Friction indicates an opportunity to transform your business into the next more sustainable operating phase. If you respond intelligently rather than react impulsively, you can elevate your awareness and actions from fire-fighting to systems thinking.

After all, you cannot continue to build a business or a team that is carried on your back. What if you experience an unforeseen life crisis that takes you out for months? Or a global pandemic renders your current systems (or entire business) inoperable, or you or members of your family become ill? Must everything grind to a halt? No. Remaining at the center of everything, with all the most important knowledge only in your mind, puts your business at risk.

This prompts the next question: Beyond reducing friction to find greater flow, how will you measure success once you are there? Will you keep yourself beholden to what you should measure, even obsess over, or intentionally redefine what matters?

📊 The Missing Metric

Any friction-to-flow business transformation requires not only rethinking operations, but redefining what success looks like, shifting into a more holistic vantage point of time, health, spiritual, and financial abundance.

In the years after Pivot launched, I discovered the joys of operating this way. Instead of obsessing over goals and numbers, I was open to surprises. That’s when I realized that in all the statistics available to help us better understand small businesses and the owners that run them, there is one vital metric missing.

More on that in a moment.

First, here is what we do know about how small businesses structure their time, team, and earnings. The U.S. Census Bureau defines a small business as one with fewer than 500 employees. Side note: that does not sound very small to me! Small businesses are an integral part of the economy, employing nearly half of the nation’s workforce.

Out of the 31.7 million small businesses in the United States, twenty-five million have no employees; these are known as non-employer businesses. Just over five million small businesses have one to nineteen employees, and less than one million small businesses have twenty to 499 employees. That means that non-employer businesses make up the vast majority of small businesses, but it does not mean you have to work alone. It just means you may not employ anyone full time, other than you, the owner. According to VC firm SignalFire, more than fifty million people consider themselves content creators, the fastest growing small-business segment.

Let’s take a look at how small businesses stack up to traditional metrics:

• Only 40 percent of small businesses are profitable. Of the remaining 60 percent, half break even, and half are losing money.

• 52 percent of small businesses are home-based.

• 86.3 percent of small business owners make less than $100,000 a year in take-home pay.

• 19 percent of small business owners work over 60 hours a week, with 89 percent working on weekends.

The business press celebrates companies with rapidly climbing earnings. One of the most common reports business owners rely on is the profit and loss statement (P&L) with three key figures: gross revenue, operating expenses to achieve that revenue, and net profit.

But there is a key metric missing from the P&L: time. Specifically, the time spent by the business owner, leadership team, and employees to reach these figures. Too many companies celebrated for their success lead burn-and-churn cultures where employees develop chronic illnesses they can’t explain, too exhausted on weekends to enjoy what little “free time” they have.

In the remainder of this book, I am sharing an operating playbook that has worked for over a decade of running an agile tiny team that optimizes for free time, not just revenue. I track my time through an app called RescueTime running in the background of my computer and mobile devices. My intention is not bragging about earnings, but rather showing you one route to what is possible.

Analyzing combined data from the last five years, I work an average of twenty hours each week, with $505,000 in gross revenue. I earned an average of $257,250 in net profit; $330,250 if you include my salary, since I operate as an S-Corp. I am my sole employee. I spend an average of 832 hours per year at the computer—a traditional nine-to-five would be twice that at minimum—and I rarely check email or do work on my phone. Those extra thousand hours saved add up to 30,000 hours over thirty working years. I take two full months off each year, and do not schedule meetings on Monday or Fridays, or before 11 a.m. or after 3 p.m., with rare exceptions. I consider four to five deeply focused computer hours each day full, sandwiched between two-hour wind-up and wind-down rituals that are as vital as the work time within.

My three ongoing team members average five hours each week to achieve these numbers, up to ten for brief windows during our biggest launches. When working on new projects, I often partner with specialists, such as a brand strategy firm (itself a Delightfully Tiny Team) every five years or so. I also work with professionals such as an attorney on monthly retainer, and an accountant that I meet with quarterly. I spend approximately $1,500 per month on software to achieve greater efficiency.

You can see a list of the nearly sixty recurring software services I use to run my business (with the monthly investment for each) in the online resources that accompany this book at ItsFreeTime.com/toolkit.

Contrast this with many executives and business owners who work long hours every day of the week, barely breaking even after accounting for team overhead, from the smallest shops to the most well-funded venture-backed start-ups. Franchising expert George Knauf said that throughout his decades of consulting, the owners of septic tank businesses were by far the happiest he encountered. Who was the most miserable? CEOs of Fortune 500 companies. The latter were stressed, constantly on the road, buried in emails and meetings, and pulled away from their families. One study found that Fortune 500 CEOs averaged only twenty-eight uninterrupted, productive minutes a day.

My friend Edward, a seasoned media executive, confirmed this. The happiest person he knows living in the Hamptons is Bob, the man who owns a gunite pool installation company there, not the well-to-do Manhattanites hiring him. Edward met Bob during a business offsite on Parrot Cay, a private island resort in Turks and Caicos. Meanwhile, Bob was there with his family on a lavish vacation. After striking up a conversation at the bar, Edward described Bob as radiant. He was tan, fit, and retired by his early fifties, with a beautiful family and kids he proudly put through prestigious Ivy League universities.

Allow me to introduce a new metric: the time-to-revenue ratio (TtRr), or if you prefer, the time-to-profit ratio (TtPr). These figures reflect the idea that we can optimize for revenue, ease, and joy at the same time; they are not mutually exclusive. Calculating your time-to-revenue (or profit) ratio means evaluating not just what you earn, but how much time it took you and your team to achieve those results. A larger TtPr percentage is good; it means you are achieving a higher return on investment (ROI) on the time spent to yield those profits.

To calculate your time-to-revenue ratio:

1. Divide your company’s revenue* by 1,000

2. Divide that figure by the number of hours worked in that time period**

3. Multiply by 100 to yield a percentage

Revenue can be substituted for profit and/or owner pay. *You can run these calculations by owner’s time only or by hours worked by the entire team.

To illustrate this with a personal example:

Owner pay of $330,000 / 1,000 = 330

Owner time to achieve that = 912 hours*

330 / 912 = 0.3618

0.3618 x 100 = 36% TtPr

For contrast, if I had worked 40-hour workweeks: (330,000/1,000) / 1,920 = 17% TtPr

The number of hours you consider abundant is however many you define that to be; there are no minimum or maximum hours, and you are not a better or worse business owner for working more or less. Some businesses—restaurants, farms, brick-and-mortar shops—often require more time by nature than those that are information-based or working remotely.

Not all time spent is equal, either; more on that in the Design stage (Part Two). As I sprinted to finish writing this book, I ended some days on deadline bouncing with enthusiasm. During other weeks, where my primary goal was catching up on email, I left long days feeling drained and dejected, despite my best efforts to shift into a more positive mindset.

Assess your ideal TtRr by how long you are energized by meaningful work, eliminating as much busywork as possible along the way. Think of it like weeding a garden. Busywork weeds will always resurface, but you will get better at spotting them by measuring your TtRr alongside other key business metrics.

There may be some “busy” work that others hate, but that you happen to love; I say keep it! There is no sense in delegating away everything you enjoy. Notice, though, when you procrastinate with smaller items in your comfort zone instead of tackling the twofold challenge of trusting someone else with those tasks, and stretching yourself to do the harder, more strategic work.

When I shared the TtTr concept with Michael J. Consuelos, a military veteran and pediatrician who pivoted to medical consulting just before the pandemic, he immediately put it into practice. One of his clients, a three-year-old healthcare services company with forty employees and ten million dollars in annual revenue, was growing at breakneck speed. Michael noticed that their “all in” approach was relying on increasingly long hours. “I could smell the early smoke of burnout,” he said, as they struggled with prioritizing. “Everything needed to get done today.”

So Michael posed the TtTr question to their founder and CEO: What’s your time-to-revenue ratio? He explained that the ratio is improved by reducing time for the same revenue, or increasing revenue for the same amount of time spent. If you have too little time, or are making too little money, then there is room for improvement.

Michael also noted the time and opportunity costs of chasing initiatives that would not pay well, projects that distracted and detracted from work the company could perform better, faster, and with healthier margins. With this framework in mind, the CEO initiated conversations about his team’s time investments, reprioritizing as a result.

For a segment of business owners with deliberately small teams, and no intention to grow them, time freedom is the ultimate aim, as measured by this time-to-revenue ratio. In many cases, they would not accept opportunities that would double their earnings if they also required quadrupling their time investment—unless the project was particularly meaningful, or they were at a stage in life where they needed a capital infusion.

Consider a hypothetical, if you were already earning enough to live on: Would you accept one million dollars if it meant working seventy to eighty hours per week, doing work you did not enjoy, for one year (no cancellation allowed), with a demanding and bureaucratic client?

🏝 High Net Freedom

I encourage you to pose this “million-dollar bureaucratic client” question to others; the answers may surprise you. As one person pointed out, it’s a PG-rated version of the 1993 movie Indecent Proposal starring Demi Moore. Or for a twist, consider the premise of the History channel’s reality TV series, Alone. Would you attempt to survive one hundred days in the Arctic, alone, for the chance to win one million dollars?

As a small business owner, you are in a privileged position if you know you can earn this much through your own efforts, or you are someone for whom no exchange of money is worth trading time doing work you hate. In truth, to work at all is a privilege: to breathe, to live, to have clean drinking water, to get a full night’s sleep, to move comfortably in one’s body.

I wrote Pivot for a group I consider high net growth, those who are asking not only “What am I earning?” in any job or income stream, but “What am I learning? How am I growing?” When those needs are being met, often in parallel, they aim for also making a broader positive impact. If you are reading this in your free time, you are certainly high net growth. You are likely high net impact, and it wouldn’t hurt to be high net worth—inside and out, of course. But there is another core value that will supersede all of these: high net freedom.

High net freedom means you most likely do not want to become an operator of a huge business, with investors or shareholders to answer to, managing an org chart five layers deep. You want to be free to move, to do your best work. That said, emergencies happen. Sometimes force mejeur occurs, and you need to make sacrifices to survive.

The million-dollar bureaucratic client question sparked a fascinating discussion among my friends, family, and private podcast community.

Some would take the job, if they knew it was funding their bigger creative dreams. Others remarked that they had already worked this way earlier in their career at far lesser pay; at least this way they were ostensibly being recognized for their efforts. Some said if they knew their existing skills would never yield this much, an assignment like this could be game-changing.

For others, no amount of money was worth sacrificing their health and relationships. One person, citing the high opportunity costs of time away from his creative projects said, “No way. I would rather make thirty grand, with plenty of time to build my own million-dollar assets.”

Uzma Iqbal was faced with this type of decision in the early aughts, when she was graduating medical school to become an oncologist. She had two job offers: one for a $120,000 starting salary, and the other for $500,000. The former would offer intangible rewards beyond financial gain, while she knew the latter would box her in. She took the lower paying gig.

“Boy, I was right,” she said. “I never made much money in that first job, but I learned the skills to launch my own practice, perhaps now even making up for some of that money ‘lost.’”

She asks herself a version of this question every day, reflecting on what her number would be. “One million dollars is an attractive number,” she said, “But it’s not the one that I would give up what I am doing now for, or how I am working.” Uzma is content with how she is running her medical practice, with the flexibility to toggle her hours up or down.

Short of the hypothetical million-dollar client, the challenge for many business owners is ignoring the siren song of money for money’s sake, despite survival fears for yourself, your family, and the business. Forgoing money as the main driver requires trust, because it is counter-cultural to imagine freeing up time and energy first, so that you can attract new and better opportunities next. After all, most business advice centers upon cash flow for a reason: without it, your business won’t survive.

I challenge you to equally prioritize ease and joy on your path to profit. Not ease in the sense of laziness, though many successful entrepreneurs are known to tout “strategic laziness” as the secret to their success, but the ease of working in harmony with your strengths and your team. The intersection of revenue, ease, and joy is where you will find free time. Within your business, plot your current and potential revenue streams across these areas, looking for sweet spots that are abundant in all three.

I say and do this—aiming for the intersection of revenue, ease, and joy—as the breadwinner for my family. My husband, Michael, a contemporary artist, bootstrapped his way from Beirut to New York by running a graphic design business while doing voiceover work on the side, before completing his master of fine arts. My business is our main source of income. The principles I am sharing with you in this book support our household; my business is not a part-time supplement that requires a second full-time earner to be realized. As the primary earner, it would be tempting to take on the pressure of working around the clock, but I refuse to work this way, having hit burnout too many times before.

The Free Time Framework is a continual process to free your mind, time, and team. The specific software tools will change and evolve. By understanding the systems design process behind them, you can reduce friction and overwhelm. Following the Free Time Framework at a macro level for your business, and following it at a micro level within day-to-day work, will not eliminate burn-it-all-down mode forever. But it might just give you renewed hope for the future of your business, and your ability to steer your ship sanely and sustainably—dare I say—even joyfully.

🚀 Free Up Founder Time: Escape Velocity

Ideapreneurs require space and focus. You need time to wander, dream, reflect, and strategize. Every business owner is in the idea business: Your strongest asset is your mind, not your labor, at least once you move past the stage of solely delivering services. There is no scenario where a burned-out business owner does better than one who is energized, expansive,

and engaged.

If your tires are spinning in mud, failing to gain traction, you need more of what I call Founder Time. You do not free your time by earning it, getting “enough” done, or waiting until no one is asking you for things. You free your time by freeing your time. Make your Founder Time windows unavailable to others starting now.

Yes, right now . . .

Start by creating a two-hour Founder Time block on your calendar that recurs weekly, during a time of day when you are most energetic. As they say in personal finance, “pay yourself first.” Do not look for small segments sandwiched between others’ requests; reserve windows that suit you best. During that window, you can tackle strategies from this book, along with the projects that will make the biggest impact on your business (more on this in Part Three).

Remind yourself that Founder Time is the most indispensable resource you have for building everything else in your business. It is the essential element to achieve escape velocity. In technical terms, this is “the minimum velocity that a moving body, such as a rocket, must have to escape from the gravitational field of a celestial body, such as the earth, to move outward into space.” Constructing a Delightfully Tiny Team is an important vehicle toward free time, but freeing your mind comes first, by committing to building a business that runs smoothly without your constant presence.

One of my long-time friendtors, Michael Bungay Stanier, achieved Founder Time escape velocity, even if he sees his newest venture at an earlier stage. Michael exited the company he built for twenty years, Box of Crayons. He remains the owner and receives quarterly profit payouts, but he is no longer CEO, responsible for managing a growing team of over twenty people. Instead, he hired a president, training her over a three-year span of time, so he could transition out with confidence that she had the role covered.

Now Michael is focusing his energy and efforts on a new direction of creative expression by returning to a Delightfully Tiny Team of two to three core members (including himself), bolstered by a network of specialists for various projects ranging from a next book, a new podcast, a two-day literary festival, and yet-to-be-imagined projects that align with his best expression.

I had a fun Founder Time experience while working on the final edits for this book. I meet monthly with my business attorney, Francine Love, who had recently read an advance copy. When I moved our upcoming call to a Friday due to a conflict, she responded saying that day was newly unavailable.

“Sorry, I have started Founder Fridays for the summer (and hopefully beyond),” Francine wrote. “It was, in part, inspired by your book, so you can only blame yourself. :) Can we look at the next week?” I smiled. Although it meant waiting a few extra days, I was thrilled to know Francine was claiming her Founder Time!

Consider how you could free up Founder Time even more expansively. Graphic designer Stefan Sagmeister is famous for taking creative sabbaticals every seven years, closing his New York studio for one year. In a 2009 TED Talk on “The Power of Time Off,” he said:

We spend about the first twenty-five years of our lives learning, then there are another forty years reserved for working. Tacked on at the end are about fifteen years for retirement. I thought it might be helpful to basically cut off five of those retirement years and intersperse them in between those working years. That’s clearly enjoyable for myself. But even more important is that the work that comes out of these years flows back into the company and into society at large, rather than just benefiting a grandchild or two.

Sagmeister has become renowned for the ideas he develops during these sabbaticals, and the work his team produces in the years that directly follow.

Achieving Founder Time escape velocity by following the Free Time Framework means your business and personal needs are abundantly met by recurring revenue and a well-oiled team machine. You are no longer conflicted about what to work on, how to find the time, or how to train new team members. Nothing is ever static, certainly in business, and nothing is guaranteed. However, there is a point of mastery and maturity—of the leader, the team, the operating systems, and the work itself—that becomes a virtuous cycle of sustainable systems and meaningful creativity.

Now, let’s make sure you are building on solid ground.

🌊 Scale: Be Ready for a Big Break

“Overwhelm is the abundance you asked for.”
— Unknown, via Jasmine Star

Are you ready for your big break? Or would your business break? Would you gleefully ride the wave you have been preparing for, or would your business systems collapse under the crush of surging interest?

One thought exercise I encourage my team to ask regularly is, “Are we Oprah or Tim (Ferriss) ready?”

This is less about magical thinking, waiting for a lottery ticket success shortcut, but rather encouraging an ongoing systems audit by imagining interviews with hosts I admire. Would my team and I be ready to catch the wave of interest and incoming leads that either of their two podcasts would generate, without our systems crashing?

If you scale with sloppy systems, your problems will only multiply. Hence, the adage from Bill Hewlett, co-founder of Hewlett Packard, that “More companies die of indigestion than starvation.”

One of Tim Ferriss’s readers labeled this the “hug of death” resulting from outsize traffic due to products he recommends. If the small companies don’t see it coming, they sometimes run out of inventory, servers crash, or they experience other flubs. These are the last problems a company wants to face when meeting outsize incoming demand.

Make it easy and inviting for big (the biggest!) opportunities to come to you. Be ready before the wave, not scrambling or fumbling after the fact. In systems-thinking terminology, this is known as expanding service capacity and addressing limits to success. Service capacity refers to your team’s abilities to meet demand, the maximum level of service production; the latter can occur when achieving market saturation due to your success.

This “big break” thought exercise precipitates at least five categories of questions:

1. Do you have scalable streams of income that can capture the incoming interest heading your way, without you or anyone involved being the bottleneck?
   
   Can customers purchase courses and services without being limited by your time-for-money capacity? What if 1,000 people were eager to purchase something from you — could you handle that? In terms of revenue streams, are you selling products to support that? What if it were 10,000 or 100,000 people clamoring for your offerings?
   
   Tattoo artist Scott Campbell started minting his designs as non-fungible tokens (NFTs) based on blockchain technology. With his online marketplace, All Our Best, he experiments with transcending the typical time-for-money exchange, as many tattoo artists are paid by the hour for sittings. In contrast to artists who produce physical assets like paintings, tattoos are more ephemeral; they fade, and can’t be passed on from one recipient to the next.
   
   “Musicians don’t get paid by how long it takes them to create a song,” Scott said in a New York Times interview. “You’d never go to a gallery and think, How long did it take the artist to paint it? I’ll pay him for his time.” NFTs allow Scott and other artists to receive royalties each time their digital tattoo design changes hands, giving the work life beyond its application onto a human canvas. When someone purchases one of his NFTs, they also get scheduling priority for a tattoo sitting.
   

2. Are your team and systems prepared to handle this inflow of traffic and interest?
   
   Could your systems for customer service and fulfillment handle ten or one hundred times the load? How can you simplify so that team members with less skill and experience can complete related tasks?
   
   My brother, Tom Blake, is the co-founder of Flexible, a real estate investment company that makes it easy for property owners to sell, partner, or lease on their terms. His vision is to create a successful company that runs on its own, through sophisticated repeatable systems. A question he asks himself when upgrading his operations with scale in mind: “How can we design roles and responsibilities so a virtual assistant can have the same output as a rockstar?”
   
   Prior to documenting his marketing systems for handling leads, it seemed necessary to have experts handle these tasks, ones he paid nearly $150 per hour. With detailed systems and documentation in place, he is now able to work with virtual assistants to fulfill many steps in the process at $15 per hour, ten times less than his initial expenditure. This has a dramatic impact on his bottom line for a central business area, while ensuring Flexible is ready for interest surges.
   

3. Would you be proud of what people are seeing on your website landing page?
   
   Is there a clear call-to-action to sign-up for your newsletter or one next step to engage further, and is it relevant to the audience coming over? Are your welcome auto-responders fresh and current? Are your about page and bio updated?
   

4. Is there something special you would like to create for this audience in particular?
   
   One common technique is to say, “Welcome {publication} readers (or listeners),” briefly re-introducing yourself, and offering follow-up content related to what you were featured for on the larger site or show. Perhaps you would like to offer a special discount or opportunity to engage with you further, maybe even setting up a free workshop a few weeks out that this new audience can enroll in to get to know you better. In other words, how can you roll out the red carpet for this group?
   

5. Are you ready to filter out the scrutiny that an influx of strangers might spark?
   
   Going mainstream requires a thick skin. You will be exposed to new people who do not already know and trust you, who might be having a tough day, or who might decide for no good reason that they don’t like you. Create a plan for moving past, or ignoring, unhelpful criticism from the peanut gallery, people who would rather poke holes in your business than provide constructive feedback, while still making room for your inner circle to point out what you might be missing.
   

The point of this thought exercise — reviewing these five “big break” considerations — is not to pin all your hopes on one magical savior, but rather to foster an ongoing state of readiness that energetically invites — even courts — opportunities to come your way.

Are you the bottleneck limiting your income potential? Are there areas hiding in your operations where things could break at the worst possible moment?

Think through surges in advance, step by micro-step. Imagine you are running an emergency preparedness drill with your team: Does every person know what to do if and when a big interest wave hits?

This is an excerpt from my third book, Free Time: Lose the Busywork, Love Your Business (Ideapress, 2022). Get instant access to the Free Time Toolkit, and subscribe to the W3 award-winning podcast Free Time to set your time free through smarter systems, with episodes published every Tuesday and Friday.