The Brutal Cost of Keeping Your Options Open | (#101) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Welcome to the Beyond Success Podcast: Psychology and Philosophy for Achievers on the Bigger Question Behind What You’re Building.

So, you’re probably pretty good at time management, like you have an actual system and everything, and that system probably works pretty well for you, and maybe you’ve kept it working for years, which is where almost everyone else falls off. You’ve read the books. You’ve taken the trainings. You’ve run the methods, the ones with all those acronyms and maybe the methods without the acronyms. You’ve built a calendar that holds up under pressure and you defend it, and probably, you get more done before 10 in the morning than most people manage in a whole day.

But every one of those systems answered the same question, which was, “How do I fit more in?” That’s true of the good methods and it’s true of the ones that you abandoned halfway through, but none of them really answer what deserves to have your time in the first place and how you would know. [00:54.6]

Time management assumes that your problem is throughput, that there are too many tasks being asked of you and not enough capacity in you, so you go and build more capacity, but, actually, throughput was never the real problem. The hours are finite and no method anyone has ever invented for time management has ever produced more hours.

You can get faster at spending those hours, but they’re the same 24/7 that everyone else has, so optimizing ends up being what you do instead of deciding the bigger questions, and probably, you’ve gotten very good at that optimizing, which is why it’s taken this long for anyone, including you, to notice what it’s actually been replacing.

By the end of this episode, you’ll be able to tell a time problem from a decision problem, and you’ll stop applying time solutions to what’s actually a decision. You’ll know what it takes to make a commitment that you can’t easily reverse, which is, as far as I can tell, the only way anything meaningful in a life ever gets built, and you’ll understand why keeping your options open for as long as you have been has been costing you the very thing that you are keeping them open for. [02:04.3]

Okay, so first the math and I’m going to be drawing here from Oliver Burkeman’s awesome book Four Thousand Weeks, which is on my recommended reading list on my website. Live to 80 and you get roughly 4,000 weeks. That number isn’t there to frighten you, though it might do that. It’s there to end an argument, because once you accept that your weeks are a finite number, the excuse of “I’ll get to it when things settle down” stops being a plan and, instead, becomes a decision you make. You’ve decided not to, and you’ve simply declined to admit it to yourself or to say it out loud.

The stakes here are not complicated—the next 20 or 30, or 40 years, are going to be spent either way, so the only question is whether the way that you spend them is how you would actually decide to spend them if you were to look back from the end. [02:58.5]

Now, the story you’ve been telling yourself is that being busy is a phase that you’re passing through on the way to somewhere else better, and that there’s a version of you on the far side of, I don’t know, this quarter or this round, or this raise or this exit, who finally has the room and space and can take a Thursday off without three people calling you.

Burkeman spent years inside all of the different productivity systems, so he can speak to this with some authority, and what he found was that if you get better at answering email, you get more email. Efficiency doesn’t empty the queue. It simply raises the throughput and then the queue refills to match that raised capacity—so, there is no far side, and that room that you’re waiting for isn’t actually coming, because what’s generating the volume is not actually inefficiency. [03:56.4]

Let’s stay with the systems for a minute, all those productivity systems, the time management methods, because that’s probably the part that you’re most familiar with, and because Burkeman knows this better than almost anyone else writing on the subject. He wrote a weekly column on this, on productivity and time management, for The Guardian for 14 years from 2006 to 2020, and he wasn’t like a skeptic looking at it from the outside, taking potshots at people who color-code their calendars.

Instead, he was a believer in this, and he was running the “getting things done” method, the inbox zero method, and all of the different testing, all of the different apparatuses, experimenting on himself in public and charting it out week after week. At the end of all that, he concluded that the whole project was misconceived, and he says so in the first pages of this book that time management, as it’s commonly practiced, has failed, and he describes the conventional version of it as a narrow affair concerned mainly with cranking through as many work tasks as possible. [05:03.8]

Now, for most people, that’s the easy version of the argument, and you could easily nod along to it without anything in your life changing. The harder claim is what we’re actually going to tackle here. The systems weren’t failing at their job. They were succeeding at a different job, which is to keep you occupied with a problem that you could solve, so that you never had to sit down with the problem that you can’t—and this is actually Burkeman ‘s account of it, not my interpretation of Burkeman.

He writes that the productivity obsession was serving a hidden emotional agenda and that it kept certain frightening questions at bay for him, and the same thing operates in so many achievers, but it’s almost impossible to see that from where they’re standing, because someone who is genuinely overloaded and someone who is avoiding an important key decision look exactly the same from the outside. Both of them are busy, both of them are working late, and both of them can give you a completely honest account of where the last four months went, with meticulously detailed spreadsheets. [06:12.4]

There is a key difference between them, of course. For one of them, the volume is genuinely there, but for the other, a good part of it exists because he hasn’t decided on something important. For example, he’s kept three options alive that he could have narrowed down to one a year ago, and keeping all three alive generates more meetings and research, and conversations and discussions, and a certain amount of anxious rereading of the same information. If you picked one of the three, two-thirds of that would stop existing, and it wouldn’t get delegated to anybody else either—which, of course, raises the obvious question: Which one are you? [06:54.4]

Nobody watching from outside could tell you because, from the outside, the two cases produce the same evidence, your board can’t tell you, and your partner, girlfriend, boyfriend probably has a theory, but he or she is working from the outside, too. There is a test, though, and it doesn’t depend on how any of this makes you feel. It’s simply two questions with concrete answers, and I’ll give them to you once we’ve dealt with why the volume keeps refilling in the first place.

So, why does it refill? Burkeman’s answer is that productivity is actually a trap and he means that fairly literally. Becoming more efficient makes you more rushed rather than less, and clearing the decks just makes them fill up faster. His reasoning is that efficiency will never produce the feeling of having enough time, because demand will always rise to absorb whatever gains you make. So, you get things done, and then getting things done generates new things to do. [07:58.0]

The reward for being the person who handles things is more things, and the reward for being reliable is more reliance. You built a company where your judgment is the constraint, which was probably the correct decision at the time and may still be, but it means that every decision of consequence now routes to you and every efficiency you install simply increases the volume that routes to you. You got faster, so now more can arrive. You solved the wrong equation, but you solved it beautifully.

Now, there are founders whose overload is genuinely like a bad quarter and like a payroll problem and nothing else, so if that’s you, then me telling you that you’re secretly avoiding some decision would be wrong and insulting. So, here are those two diagnostic questions I promised and you’re the one who will answer them—first, if your calendar were cleared tomorrow, would there be less to do in a month, or would the same volume find its way back in through a different route? Second, is there a decision that you’ve been gathering information on for longer than the decision itself would take to make? [09:10.7]

Okay, if the volume refills and there’s a decision that’s been pending for a long time, maybe a couple years, then what you’ve got is not a scheduling condition. Okay? So, no scheduling solution is going to resolve that. But if the problem doesn’t refill and there’s no decision sitting there, then this episode isn’t actually for you. Your system is fine and you should probably keep at it and go have a good quarter, okay?

For everyone else still here, most people, there’s a deeper claim, and Burkeman makes this in his book, and you’re probably going to resist it. That point, that claim is, you don’t have time. Now, he’s drawing on Heidegger here. The idea is that we don’t get time or have time. We are time. We’ll never get the upper hand over the moments of our lives, because we’re nothing but those moments. [10:04.2]

Treating time as a resource means treating it as something separate from you, something you deploy well or badly, the way you would deploy capital, but the hours aren’t an input to your life. The hours aren’t what make up your life, which means a well-managed decade and a decade are actually the same decade.

There’s a tragic joke buried in this, which is that the better you get at the system, your productivity or time management system, the more of your life that system covers, until, eventually, that system is what you did with the 4,000 weeks. You spent your life getting ready to spend your life.

Burkeman has a term for the condition that all of this arises from. He calls it existential overwhelm, and he means the gap between everything that genuinely seems worth doing and what any one person can actually do—his point is that this isn’t a personal failing and it isn’t fixable, because it’s the permanent condition of being a finite creature in a world containing more good things than ours that we have. [11:15.3]

For those who have read or heard my work on death anxiety, this is a manifestation of trying to deal with death anxiety, which brings us back to where the last episode left off. The late Clayton Christensen of Harvard Business School showed you that you had been measuring the wrong things. Burkeman goes a step further and says that even once you’ve got the right method, you still have to give things up.

Now, the Latin is useful here and people don’t usually say this about Latin. The word “decide” comes from desidere, which means to cut off, and Burkeman points out that it’s a cousin of homicide and suicide, which share that same ending and mean roughly what you would expect. So, a decision, if you take the word literally—“literally” literally—isn’t the selection of an option. It’s the killing off of the others. [12:09.7]

Burkeman put the consequences more gracefully than I would. He says that any finite life, including the best one you could possibly imagine, is a matter of ceaselessly waving goodbye to possibilities, so every yes you say is a no to a very large number of other things that you’ll now never do, and most of them might have been perfectly fine.

But he does something more interesting than end there with a mere shrug, because he takes that fear of missing out and flips it into its opposite, which is the joy of missing out, JOMO, and the reasoning here isn’t just cute or sentimental. His grounds are that giving up the alternatives is precisely what makes the thing you end up choosing mean something at all, because if you never had to foreclose on the others, then you never committed to this one. You just had a preference. [13:09.4]

Now put that in your own terms for a second. You’ve been treating optionality as an asset, and in business, it very often is. Whether that’s keeping three suppliers in play or not signing the exclusive, or staying liquid, or waiting for better information before you commit more capital, and most of the time that’s exactly right and it’s part of why maybe you’ve done so well. But if you take that and apply it to a life, that same habit is the reason nothing in the personal column has actually been built properly.

It’s one instinct producing opposite results in two different important places, and you probably haven’t connected them, because one of them has been rewarded for 20 or something years, like you cannot half-marry someone. There is no such arrangement available. You cannot keep a deep friendship on a maybe, because the friend can tell, and eventually, the friend acts accordingly. [14:10.8]

Everything that pays off over decades requires the cutting off first. It requires you to foreclose the alternatives before you have any way of knowing for sure whether you were right, which is maybe an appalling deal to you, but it happens to be the only deal on offer that would work. So, the weeks are numbered and this is what deciding costs, which is everything else you might have done instead. So, what deserves those weeks? [14:43.5]

Sometimes, the real problem isn’t more effort or more motivation. It’s knowing the right direction. A lot of people listening to this podcast are capable and driven. Things still look fine on paper, but life still feels strangely flat. When that happens, more advice usually isn’t the answer. Clarity is.

I’ve put together a short assessment that takes about two minutes. It’s simply a way to see which area deserves your attention most right now, whether that’s relationships, decision-making, or how pressure is being handled day to day. Based on your responses, you’ll be sent a short set of master classes related to that area.

If that sounds useful, you can find it at DTPhD.com/quiz. That’s “dtphd.com/quiz.”

In this episode, I’m not going to answer that directly. That question needs a whole episode of its own and it’s coming up, so hit subscribe and stay tuned. What this episode establishes is that the question has a price that’s paid in alternatives that you’ll never get to have, which matters especially for achievers who maybe are good at a lot of different things, because most people who ask, “What deserves my life?” are asking it as though the answer were free, as though you could identify the right thing and then simply add it into or along with what you’re already doing, but you can’t just add it in. You can only trade for it. [16:08.1]

Let’s talk about what you’ve been trading and what you’ve been getting for it. Maybe you haven’t married yet—and if that’s where you are, I’m not saying this as a criticism. It’s just the situation, just pointing it out—and the friendships that mattered most to you 10 years ago have probably thinned out by now, which isn’t the same as saying that they’ve ended, because nobody really ends these things, right? Nobody falls out with anybody, really. They just went unattended for a long stretch, which is what happens to anything when there’s nobody scheduled or assigned or responsible for attending to it.

There’s nothing broken about you. You’ve just been deferring, and you’ve been deferring on the perfectly reasonable-sounding assumption that deferral is free, that whatever you’re putting off just sits there in the same condition that you left it, waiting for you to come back to it when the quarter is over. [17:02.1]

Let’s look at the relationship first. You’re waiting for the timing to be right, right? Which means after this round or after this exit or this raise, or after whatever the next thing turns out to be, and I’d point out that the next thing has so far always been followed by another next thin. But you’re not holding those years in reserve while you wait. You’re spending them and they were the ones that you had, and there’s no magical account somewhere, where those years that you kept putting off are piling up on your behalf while you’re busy.

The math on this is completely unsentimental. If you want a marriage that’s good at 20 years in, you have to start it, and there’s no way to have a 20-year marriage if you start it this year, not for any mystical reason, but because of time in the calendar. [17:51.2]

So, what actually changes if you act on this? You’d stop treating the relationship as if it were the prize that shows up after all the building and the perfecting of yourself is finally finished, and you would start treating it as one of the things that you’re building. Fund it now out of the same budget, competing for the same hours as everything else, which means it stops being a feeling that you have about your future and becomes a line item where previously there wasn’t even one.

Now, as an important side note, let’s look at the second column of the ledger. Those years were also hers in that relationship. A woman who waits out a man’s timing is spending her 20s or 30s or whatever years it is inside his optionality. She’s living inside a decision that hasn’t been made by him, and she doesn’t get those years back either because the 4,000 weeks are hers, too, and some number of them went into waiting for you to be ready. [18:53.2]

You weren’t doing anything to her. You were treating a decision that involves another person’s life as though it were yours alone to schedule, and that’s the part that optionality hides from you—it feels like a position that you’re holding privately, something happening to you inside your own head, but it isn’t private at all, because whoever else is involved in that relationship is standing inside the consequences of it with you.

Then there’s friendship, and this one might have a harder edge to it because it can’t be repaired with money. The friend who knew you before any of this building can’t be acquired later at any price. A 20-year friendship takes 20 years. You could offer someone $10 million dollars to have known you in 2009, but it would be logically impossible for that new friend to take that deal. Again, there’s the other side of it. That friend has been on the receiving end of every unanswered message and every dinner that you rescheduled twice and then forgot about, and at some point, he just stopped initiating. [20:02.1]

You might have noticed that and then just read it as him getting too busy as well, or drifting or just life happening, but in this case, it wasn’t neglect on his part. It was a conclusion that he drew, a reasonable one, about where he stood with you, and he worked it out from the evidence you were giving him and the evidence was sound.

So, deferring a friendship doesn’t leave it sitting there intact and just waiting for you. It teaches somebody that he’s optional, and people who learn that tend to believe it and then they will act on it, which is what you’ve been watching happen, and is completely reasonable from their side.

Burkeman has an argument about this that runs directly against many people’s instincts. He argues that individually controlling your own schedule can cost you the ability to coordinate it with anybody else and his phrase for it is that “your time can be too much your own.” Your time can be too much your own. [20:58.0]

Think about what you’ve optimized for: autonomy over your calendar, control over your calendar. Nobody else’s rhythm is dictating it, nobody else’s claim on your Tuesday or Thursday. That was the goal, let’s say, and let’s say you’ve achieved it. But autonomy over your calendar is actually what makes it possible for no one to be on it, and the freedom and the emptiness are produced by that same arrangement. A life doesn’t get assembled out of what’s left over after the important things are done, because what’s left over is never enough, and it’s never the good part either.

Now, none of this asks you to be less ambitious. This is not me telling you to want less. What it asks of you is that you fund the slow things, slow important things, on the same conviction that you once funded the company before it had revenue. You put substantial money and substantial years and time into something with no evidence yet that it will work, because you have decided that it was worth building, and that’s the right approach that you need now to apply to your life. [22:05.8]

Okay, so that’s the approach and I’m going to tell you now what to do with it, and you’re probably going to hate the word that best encapsulates it: “settle,” though settle in a good way, so stay with me here. Burkeman builds this on an argument from the political philosopher Robert Goodin, and the argument goes something like this—you have to settle in a relatively enduring way on something that becomes the object of your striving, or else, the striving does not count as striving at all. It’s just mere motion.

Okay, then Burkeman escalates that and this escalation is really important, because he says that, ideally, you settle in a way that makes it hard to back out. As an example, you could do this by moving in together or marrying, or having a child. A dear friend of mine, Henry Chung, gave a speech at my wedding and he cited this beautiful quote from Rumi, “A thousand half-loves must be forsaken to take one whole heart home.” It kind of makes the point for me I think. [23:05.7]

Now, why would irreversibility be the point rather than an unfortunate side effect? Because an irreversible commitment makes you answerable to a particular person. Somebody can now hold you to something. She can say, “You said you would,” and the sentence has force because you can’t simply withdraw at low cost and go back to how things were easily, which is also what you’ve been avoiding and it also happens to be the entire value of that arrangement.

A promise that you can withdraw cheaply is not a promise. It’s a stated preference held down by nothing but your current mood. What makes the striving count is that somebody else is now entitled to rely on it. There’s evidence that this makes people happier actually. Daniel Gilbert, famous psychologist, ran a study with posters, where some people chose and could swap later, but some chose irreversibly, and the ones who couldn’t swap ended up happier with what they had chosen. Burkeman applies this directly to marriage that spouses committed for better or worse spend less of their marriage pining after alternatives. [24:17.3]

Okay, but here’s a limit of that evidence because I don’t want this to be misunderstood or misused. Gilbert explains why irreversibility feels better afterwards. He doesn’t give you a reason to do it, though. A man who marries because irreversibility improves his own satisfaction has put the cart before the horse. He has learned a technique and hasn’t made a real promise to anybody.

The example running the other way is Kafka. He met Felice Bauer in 1912, and over the next five years, he sent her more than 500 letters, and they met in person only a handful of times. They got engaged in May 1914 and it was broken within weeks. Then they got engaged again in July 1917 and then broken by that December. Burkeman’s reading is that the correspondence preserved every possibility by realizing none of them. [25:09.5]

Let me add something more about Felice, which turned up in my research, because the story usually treats her as mere background scenery. She’s the passive victim here, right? But she wasn’t ruined by any of this. She had an executive career at a Berlin firm selling dictation machines. She ended up marrying in 1919 after all that and had two children. She got her family out of Germany to Switzerland in 1931, into the U.S. in 1936, and then she died in New York in 1960 at 72, having built a life.

What she doesn’t get back, though, are those five years spent inside a correspondence with a man who could not choose. Five years of a finite life were spent anyway, which is really the point, because deferral doesn’t have to ruin a person in order to have taken something from her. [26:03.6]

Now, the honest objection is whether any of this is just noble-sounding resignation, because if you tell an ambitious person to accept his limits, you may have handed him a philosophy for stopping. That objection has been made. The law and religion professor John Inazu read Burkeman’s book as merely an argument for the power of giving up hope. Okay, so this deserves an answer rather than just a dodge.

I am not recommending less action. I don’t think Burkeman is either. I’m recommending that the action be irreversible. Keeping your options open is the passive posture, but committing is the demanding one, and the person who won’t settle, or maybe a better way to put it is commit, isn’t holding out for more. He’s declining to spend, but that account expires. You were never going to get all of it, and nobody ever has. The only people who got anything worth having got it by giving up the rest on purpose, early on enough. [27:07.5]

Let’s review what we’ve covered so far. You’ve got roughly 4,000 weeks in your life and no time management or productivity method has ever produced more time. Efficiency raises your throughput, but the queue refills to match, which means those systems were never solving the real problem. They were occupying you, keeping you busy inside of it, instead of solving the real problem.

Deciding means cutting off, which is why the personal private column has stayed empty, while the options stayed open—and the corrective for that isn’t more discipline or willpower, which you already have in quantities that most people would envy. Instead, it’s a commitment that you can’t easily reverse made before you can possibly know for sure whether it was the right one to somebody who is then entitled to rely on it. [27:57.8]

Okay, let me illustrate this with a case study for my own practice. This is a composite so that we can maintain confidentiality here. The substance is accurate. Okay, a founder in his mid-40s came to me with an unusually good relationship to time. He was genuinely disciplined, lots of willpower, and his system that he would start at the beginning of the week with multiple hours every week worked for him.

So, what he brought to me, ironically, was a kind of scheduling question. He wanted to know how to make room for a relationship without losing the operating rhythm that he had spent over a decade building and perfecting and honing.

What he concluded after we had examined it for a while was that he’d had room actually for years. He had been running a search rather than making a choice. He had kept several possibilities open on the reasoning that more information would eventually produce more certainty, but the years that he spent gathering that information for that certainty were the years—and that was his conclusion, by the way. It wasn’t just a verdict I handed him. He came to that conclusion. [29:07.5]

Nothing about him was failing, right? He had applied this time management productivity method that works so beautifully on the solvable problems in his career and work to a problem that only resolves through commitment.

So, let me tell you what happens if you do nothing with what we’ve covered, okay? If you keep the options open and nothing forecloses, which, I get it, is appealing, but it’s also a trap and it operates on you whether or not you’re even paying attention to it or even know about it, because the weeks spend themselves regardless of whether you assign them to anything meaningful.

Ten years of staying available is still 10 years, and at the end of it, you will have the same optionality you have now, but 10 years less time to use it on. The friendships will have thinned to maybe nothing, without a single moment that you could point to and identify as the turning point when it happened. That’s what happens by default when nobody takes responsibility and intervenes on it. [30:09.3]

There’s one more very important but ironic thing. Listening to this on its own changes nothing, or almost nothing. Now you’re informed. An episode about postponement is the easiest possible thing to postpone with. You can finish this, agree with every word I said, feel the weight of the math sitting on your chest, and then do absolutely nothing. The feeling of having addressed it is the most reliable method ever devised for actually not addressing it.

Understanding that the weeks are finite is not in itself a use of the weeks. The only evidence that any of this will have affected you is something that you have committed to by Friday that you can’t undo. So, let me tell you what it looks like if you do put this into action. [31:00.2]

Picture the person who stops trying to fit a life into the margins of the career, who cuts off the alternatives on purpose, who commits to the person or the friendships or the place before the evidence is certain, the same way he committed to starting that company back when it had no customers or revenue yet. He doesn’t build less. He builds his career and his life with the years that he’s actually got. He assigns them to something meaningful, and he does this alongside people who can count on him for a stretch that’s long enough to matter.

That’s what the 4,000 weeks are actually for. They’re not for just fitting more in, therefore, spending them deliberately on a small number of things that takes decades to become good and that you’ve decided are meaningful to you. [31:51.0]

So, you know the weeks are finite now, and you know that choosing costs, and that the commitment has to be one that you can’t just walk back easily. Now the natural next question is “What deserves that time, those weeks?” because the goal that you’ve been playing toward has a finish line and the parts of your life that matter most don’t have a finish line. I’ll unpack what that means and why that matters so much in the next episode. I look forward to seeing you there. David Tian, signing out. [32:23.4]