One of my favorite ideas is expressed in an oft-mis-quoted F. Scott Fitzgerald essay titled, “The Crack-Up,” published in Esquire in the 1930s:
“The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”
Usually, people stop the quote after this first sentence, but the rest of the passage gives useful context:
“One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise. This philosophy fitted on to my early adult life, when I saw the improbable, the implausible, often the ‘impossible,’ come true.”
I’m holding two opposed ideas in tension right now:
Having clear goals and making bold choices create powerful results.
Clear goals inhibit the achievement of greatness.
As an executive coach, my clients invest significant time, energy and resources into creating what they want in their lives, and into working with me to help them get to their next level of greatness. They have big, transformational goals: They want to transform industries. They want to create their next big dream after a successful exit. They want to lead their companies 100% authentically and powerfully as their companies grow at an improbable rate. To achieve these sometimes nigh-impossible goals, they need to make bold choices.
Often, potential clients say they want to work with a coach, like me, to ensure they remain accountable and diligent in reaching their goals and creating the life that they choose.
The goal math is simple:
Big Goals + Accountability = Success!
But the reality is more complex.
Sometimes these transformational changes take more than goals and accountability, clarity and dedication. Transformational changes in our life often entail transformational shifts in how we think, what we value and how we see ourselves.
And sometimes, real transformational change requires us to give up our goals and objectives entirely.
(Insert record needle scratch here.)
Wait…what?!
You read that correctly. I hear your skepticism and simply ask that you join me on this thought experiment for a few minutes and see if we can pass the Fitzgerald test and think differently without breaking our brains. At the end, you may be willing to free yourself of the need for specific goals for everything and leave open the possibility that curiosity, wandering and dreaming might be the key to a life worth living, and yes, greatness.
Truth One: We need bold choices to get anywhere
I was reminded recently of this amazing moment in Viola Davis’s interview on Hot Ones, a super fun web series where guests eat progressively spicier hot wings while answering questions from host Sean Evans. Evans had asked Davis (who is one of only three actors in history to earn both the Triple Crown of Acting and an EGOT!) about her Oscar-nominated performance opposite Meryl Streep in Doubt, in which her character appears for only about 10 minutes but is, as film critic Roger Ebert wrote, “the emotional heart and soul of the film.” Specifically, Evans asked about Davis’s perspective on the opportunity an actor has when their performance is limited to a single, and in this case pivotal, scene.
Davis’s response? Prepare everything you need to, and then take a risk.
“Whatever you're thinking in your mind, make a bold choice.
“Even if you think you're running in the wrong direction, make a choice so bold and so out there, and maybe it'll stick. Or maybe you'll fail—which I've done a lot—but maybe it'll stick.”
As Davis points out, when we’re given a rare opportunity, or a chance to go after a dream, it’s worth it to make a bolder choice and turn the wheel of chance rather than playing small. Those bold choices can transform our trajectories in big ways. Without taking these bold choices, we risk relegating ourselves to smaller, meeker paths, scant achievements, and paltry dreams. Or worse: we drift—we just go with the flow of life and never really get anywhere.
Or at least, that’s how the “bold choices” narrative goes. The implication is that without clear objectives and bold choices, we can’t really get anywhere at all. Inverting this truth, we can get another truth: Getting anywhere is better than drifting.
That idea is from Richard Hamming in The Art of Doing Science and Engineering:
“The accuracy of the vision matters less than you might suppose, getting anywhere is better than drifting, there are potentially many paths to greatness for you, and just which path you go on, so long as it takes you to greatness, is none of my business.”
So far, Davis and Hamming are lining up in the bold goals and choices camp! Making a big choice is better than making a small choice. Having a big goal is better than an itty bitty goal - because you might hit it big. Aim for the stars and you’ll reach the moon. Just reach for the moon…and that’s as far as you’ll get.
But Hamming’s ideas seem to open up a crack in the simplicity of goal math - maybe goals are less important than we think? He is proposing that vision and goals matter less than making a choice to keep moving forward, to never drift. And to stay open to the many paths before us. Davis says “the bolder the better" since maybe it’ll stick…Hamming seems to imply that boldness is only important in that boldness is a way of moving forward.
Truth Two: Objectives help us move in the right direction
Books like Radical Focus by Christina Wodtke popularized and clarified the “Management by Objectives” approach used at Google and other vanguard tech companies, underpinned by the Objectives and Key Results (OKRs) framework. In her book, Wodtke tells the novelized story of a young company that spreads itself too thin, spending too much time and energy focused on non-strategic initiatives instead of those that could create more profound business impact. The characters in Wodtke’s story make a lot of Davis-like bold choices but ones that are always running in the wrong direction, or just too many directions at once. Eventually, Wodtke argues, companies operating in this way run out of time, energy and resources and cease to be.
Instead, Wodtke suggests that teams align on what their objective is (a.k.a. what they define as greatness) and what it would look like when they achieve it—in other words, how could they measure that greatness? These measurements are the “key results” that help them to stay on track and even shift tracks, when necessary, to stay on course for greatness.
Hamming’s view aligns with the OKR approach: There are many paths to greatness, but we can’t try them all out at once, so let’s just pick one to start and see how we go for the next three or four months! We can change course if we need to after seeing the data.
These regular periods of setting OKRs and checking in on them are meant to keep organizations and teams on a path to greatness.
Defining what greatness is, for ourselves in our lives, and for our businesses, is no small task. This is something that I regularly help my coaching clients with, what I call “The Spice Girls Question”: What do you really really want? It’s essential to question our goals and ask why we want them. Is it because of cultural programming or parental wounds? Is what we want to create really, really aligned with our core values, beliefs and identity? After all, following a great goal for the wrong reasons is not likely to satisfy us once we get there.
It’s worth questioning the motivations behind our objectives and goals regularly, to make sure they are really really our own and will move us in the right direction.
Truth Three: Objectives rarely lead to breakthroughs
I apologize, since we’re now going to try to hold a few more than two ideas in our mind simultaneously
I’ve been reading Kenneth O. Stanley and Joel Lehman’s 2015 book, Why Greatness Cannot Be Planned, which picks apart what they call “The Myth of the Objective”. Reading this book, I found it surprising to hear the authors point out the deep flaws and contradictions they see in the notion of objectives, since they both have deep technology backgrounds, and the OKR framework is often deeply embedded in many modern tech companies and with folks of a technological bent.
Maybe there is no Fitzgeraldean paradox here. Stanley and Lehman suggest that objectives are useful for near-term, modest and conventional goals. And indeed, OKRs are often used for that specific purpose - near term goals, looking 3-4 months out.
But objectives fall apart (in their view) when we want to create something truly BOLD: shockingly, world-changingly, innovative.
Why? History is one guide.
The authors point out that in most significant technological advances in history, the “stepping stones” towards the breakthrough were usually unexpected. These breakthroughs didn’t come about by keeping a laser focus on one initial objective; finding these outcomes came from winding down unforeseen paths, sometimes completely unrelated to the initial objectives. Even the scientists who invented the laser were working on solving another problem entirely!
Stanley and Lehman give the example of vacuum tubes and computers:
The first computer, called ENIAC, was built in 1945 as a result of a two-year government contract. At 8 feet tall and over 100 feet long, it was 1,000 times faster than existing electro-mechanical computing machines at the time. Vacuum tubes made the innovation of this first computer possible. However, vacuum tubes weren’t created as part of the process of building a computer. They’d been invented 50 years earlier by people who did not have the invention of computers in mind at all; they were solving a set of very different problems.
Stanley and Lehman posit that, even with Viola Davis levels of boldness, if a scientist in 1943 had chosen to build a computer as fast as ENIAC the size of a coin—a capability we achieved decades ago – they wouldn’t have been able to. The stepping stones to get there weren’t at all obvious and were all arrived at serendipitously. They would have boldly and diligently sweated out the two years of the contract fruitlessly—which leads to the author’s broader point about objectives:
“Objectives are well and good when they are sufficiently modest, but things get a lot more complicated when they’re more ambitious. In fact, objectives actually become obstacles towards more exciting achievements, like those involving discovery, creativity, invention, or innovation—or even achieving true happiness.
“In other words (and here is the paradox), the greatest achievements become less likely when they are made objectives. Not only that, but this paradox leads to a very strange conclusion—if the paradox is really true then the best way to achieve greatness, the truest path to ‘blue sky’ discovery or to fulfill boundless ambition, is to have no objective at all.”
As the authors point out, the structure of human progress is complex: the only possible pathways to many discoveries are counterintuitive and cannot be planned ahead.
Remember the Adjacent Possible!
Transformation and innovation following these possible pathways are sometimes called “the adjacent possible,” an idea coined by Steven Johnson, who summed it up in a 2010 Wall Street Journal essay, “The Genius of the Tinkerer,” this way:
“The adjacent possible is a kind of shadow future, hovering on the edges of the present state of things, a map of all the ways in which the present can reinvent itself…
"The strange and beautiful truth about the adjacent possible is that its boundaries grow as you explore them. Each new combination opens up the possibility of other new combinations.”
If we become laser-focused on our goals, as many folks in the hustle-culture-sphere assert, we ignore all the potentially interesting possibilities that hover outside of our tunnel vision. And it is these adjacent possibilities that can unlock amazing potential.
There are so many stories of companies that pivoted into something much more interesting and much more successful than their original idea, often leveraging some forgotten side project. Just google the stories of Odeo, a podcast tool that turned into Twitter, or the tale of Flickr rising from the ashes an online RPG called Game Neverending…or Wrigley Gum, which started as a giveaway for a home goods company. The gum was more popular than the actual product and once Wrigley focused on that, he eventually unlocked a billion-dollar industry. If any of the folks behind these pivots had persisted in their objectives relentlessly, they might have missed the real opportunity.
It turns out that being laser focused on our goals can cause us to lose sight of some alternative, magical futures hovering just outside our field of vision, in the adjacent possible. And worse: goals can seriously backfire. Stanley and Lehman’s big take home is that greatness is often the result of serendipity - looking for a needle in a haystack and finding something better than you can imagine, something you weren’t looking for at all - like a magnet to find a million needles, or a pot of gold.
Truth Four: Goals can backfire
A goal or objective is the end towards which all our efforts are aimed. Stanley and Lehman point out that with an OKR framework, we’re always working towards better numbers for our key results. It’s like the childhood game of “Hot and Cold”—we all figured out how to move closer and closer to our goal as we got “hotter, colder, hotter!!”
Yet, goals and objectives are only about what we can measure. And much of life, including its ultimate purpose, can’t be well-measured. Viktor Frankl wrote about this in Man’s Search for Meaning:
“Don’t aim at success — the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it…success will follow you precisely because you had forgotten to think of it.” (emphasis mine)
Frankl lived through the holocaust in Nazi Germany. His philosophy of meaning would be striking in anyone, and is only more striking because he was able to persist in finding meaning through his horrific experiences.
So, what do we ultimately want? In other words, what’s our real goal in life? For many of us, it’s likely things that have no limitations and can’t be measured—“to live well” or what the Greeks call eudaimonia, flourishing. And yet, we often sacrifice flourishing for a smaller or more temporary goal, due to our relentless pursuit of a single-minded goal.
Emmanuel Acho knows this all too well. Acho is a former NFL player and current TV sports analyst and author. In 2023, he delivered a TED Talk entitled “Why You Should Stop Setting Goals (Yes, Really)” in which he asserts that “the surest way to fail in life is to set a goal.”
He tells his story of wanting to get into the NFL as a first, second or third round pick, but his Big Hairy Audacious Goal was *actually* to be a millionaire by 21; getting into the NFL was, he resolved, his surest path. So, he trained relentlessly in his senior year of college, bulking up and getting stronger and stronger. Two days before the NFL Combine (the “job interview” for the NFL, where potential recruits literally get put through their paces), Acho realized he had bulked up too much and needed to drop 10 pounds, which he did through ruthless fasting and sweating out water weight.
Dehydrated and stressed, he got on the starting line on the day of the Combine to do a 40-yard dash as all 32 NFL team owners looked on. In Acho’s words:
“The 40-yard dash is one of the testing metrics you use at the NFL Combine with millions of dollars on the line. The faster you run, the higher you get drafted.
“I take my mark.
“I proceed to run. I hear pop, pop, pop. I keep running. I think my heels are clicking. Pop, pop. I clutch my quad. I fall to the ground.
“It was my quad being torn off the bone. I rip my quad off the bone. I'm falling to the ground in agony in front of these 32 billionaires. I didn't get drafted in the first three rounds of the NFL draft. I made a decision that day, in that moment, to stop setting goals.”
It’s a horrifying story. Acho was so focused on his near-term goals (getting into the NFL) that he caused harm to himself and to his larger, longer-term goals.
Acho goes on to point out other ways our goals can harm us. If we fall short of a goal—for example, to read a book a month or grow your business 20%—we’re often very hard on ourselves. While we may have learned a lot from the seven, eight or even nine books we read in the year, we punish ourselves for not reading the additional three, four or five. While we may have restructured our business thoughtfully to be well-positioned to achieve rapid growth in the future, we easily dismiss or feel disappointed by the modest growth we wrangled so far.
Falling short of our goals often puts our focus on what’s missing, not what we’ve achieved.
Instead, Acho suggests picking goals that are more open-ended, like the Metallica guitarist Kirk Hammett whose goal is simply “to play my guitar a little better every day.”Such a goal doesn’t have much of a downside and has exponential upside. A little better every day compounds quickly.
Use Four layers of goals
I recently watched a video from Cassie Kozyrkov, who served as Google’s first Chief Decision Scientist, advising leadership on decision process design, AI strategy, and building data-driven organizations. She suggests setting a structured pattern of goals in three layers:
Outcome Goal: This is your North Star—something you really want to achieve that keeps you moving forward. This goal is not in your control (Acho can’t hire himself to the NFL, for example.)
Performance Goal: A way to measure success (that is ALSO not in your full control, but you can track how much stronger or faster you’re getting. For Acho, performance in the Combine was key.)
Process Goal: Something that you CAN put into your control that will help you achieve Goals 1 and 2. (For example, following a good training plan, which Acho did.)
Kozyrkrov points out that we ought to NEVER let a Process Goal take precedence over an Outcome Goal. Stubbornly running too much too fast, or running on an injured knee, according to the process plan, isn’t going to help your outcome goal. Trust the process, sure, but make sure you verify that the process isn’t moving you in the wrong direction from your North Star from time to time. Acho attempted to sacrifice short-term physical wellbeing for long-term financial wellbeing, and his gamble backfired.
In fact, we might need to add a FOURTH goal layer: anti-goals. Anti-goals would clearly describe the signs to watch out for that indicate you’re moving away from your ultimate Outcome Goal. In Acho’s case, he certainly did not want to tear his quads off the bone and spend months in rehab. It might have helped to have set an anti-goal around injury or markers of worsening physical health.
Truth Five: Goals can miss the bigger picture
Acho learned a hard lesson: goals can cost us, and sometimes more than we realize. We set goals as our current, present-day selves. Our present-day self knows only what we know now, and our vision for our specific goals is limited by that.
The 1985 classic Weird Science illustrates this point well (if bizarrely). Two computer nerds hack into the government mainframe and build “the perfect woman” inside their computer. A freak electrical accident brings their design to life. They name her Lisa.
Hijinks ensue, and Lisa helps the boys enjoy life a lot more. The boys get more mature, cooler, learn a lot, and eventually meet some real, live girls. Explaining Lisa to his new girlfriend, Deb, one of the boys says: “Deb, Lisa is everything I ever wanted in a girl—before I knew what I wanted. I know that if I could do it again, I'd make her just like you. Honest.”
The local maximum problem
Like Acho and the Weird Science boys, in setting goals with our current levels of thinking and being, we can easily choose a goal that is a local maximum. A local maximum is climbing a hill and ignoring the mountain beyond it. The builders of ENIAC didn’t know they were building a local maximum computer. For 1943, it was the top of the mountain, the best they could do…but there are always other mountains to climb.
In setting a goal we should slow down and take a look around…and ask if we’re setting the bar too low.
Goals are a Continuous conversation
Not surprisingly for someone who wrote a whole book on how conversations are the fundamental unit of change, and how conversations can and should be designed, I think goals and objectives are a conversation.
Normally, they are a one way conversation - present us, telling future us what we will accomplish.
It’s clear that we need to have a continuous conversation along the way to check in:
Are we achieving what we really, really want? Is our process of achieving our goal working for or against our real objective? Are we achieving our anti-goals by being single-minded in our approach?
The Weird Science example makes me pause - and ask a weirder question. What if goals were a conversation between my present and future self? Rather than a top-down process of goal-setting, what if we had a deep-dive conversation between our present-day self, the person setting the goal, and our future selves, the person who can see what the next mountain might be?
It’s worth pausing to ask some of these questions before setting any goals:
What does future me know that I don’t?
What does future me believe in their bones, or see clearly, that I simply can’t?
What are the BHAGS of my future self?
Fitzgerald's test of first-rate intelligence - holding opposing ideas while still functioning - offers us a framework for approaching goals: We ought to always hold our goals loosely, since we can’t always see around them to the next mountain. Goals are not just about what we want to achieve, but about who we want to become, to live a life we love. Viewing goals as an ongoing conversation between our present and future selves, rather than as fixed destinations, frees us to grow beyond our current vision. The true art lies not in setting perfect objectives and following plans with diligence, but in weaving a delicate balance between determined action and open-minded exploration. By leaving space for serendipity - those unexpected discoveries and adjacent possibilities - we might reach heights our present selves can't even imagine. Greatness emerges not from achieving our carefully planned goals, but from growing beyond them in ways we never could have predicted.