part0013

KEEP FLYING BY ACCOUNTING FOR DRAG POINTS

I’m not afraid of storms, for I’m learning to sail my ship.

LOUISA MAY ALCOTT, Little Women

Engineers have to deal with a fascinating tension: the faster the vehicle they’re designing is meant to go, the more they’ll have to account for the different ways drag is going to affect it. In a way, drag is reality pushing against their designs.

In a similar vein, reality will push against the design of your project road map. Rather than gravity and wind resistance being the dominant forces creating drag, people tend to be the dominant sources of drag for your project.

The person who’s most likely to push against the momentum of your project, though, is you, so let’s start there.

YOUR NO-WIN SCENARIOS ARE KEEPING YOU FROM THRIVING

The more you do your best work and start thriving, the more you may start pumping the brakes. Many of us ingrain in ourselves a story that to be successful in our work or lives, we have to give up something important to us.

While the details of the no-win scenarios we create for ourselves vary, they tend to look like one of the three general stories that follow:

The Success Will Wreck My Relationships tale

The Success Versus Virtue myth

The What If I Can’t Do It Again? trap

If you don’t address the no-win scenarios you’re telling yourself, they’re going to be the unwelcome gift that keeps on giving because you’ll always put a cap on the level of happiness, success, or flourishing that you’ll allow yourself. Fortunately, once you see the no-win scenario you’ve created or accepted, it’s simple to defang. (Remember: simple doesn’t equal easy.)

THE SUCCESS WILL WRECK MY RELATIONSHIPS TALE

We all know someone who estranged themselves from their family, friends, and loved ones because of their (seemingly) single-minded pursuit of success. We’ve also experienced scenarios where somebody excelled and others were hurt, bitter, or envious about it, whether it was the smart sibling whose success was used as a yardstick for their other siblings, a friend who got the hot girl/guy that the others pined for, or the promotion that created a wedge in your work-buddy group. Because the fallout of these occurrences is so common and devastating, it’s easy to encode a story that looks like “If I win, I hurt someone.”

The difficulty with untangling this particular no-win scenario is that there are shared expectations that need to be addressed because relationships are shared expectations. One party may not want to let an expectation go or see that their expectation is preventing our self-actualization. Furthermore, we may be in relationships with people who consciously or unconsciously don’t want us to grow and flourish because of their own insecurities, needs, and shortcomings. We don’t get to define what type of spouse, friend, sibling, or aunt we want to be in a vacuum.

But we also can’t blindly accept the definitions and expectations others have of us either, for it’s all too common for people to expect or want us to be the supporting character in their story. To be clear, we’re all supporting characters in each other’s stories, but we’re not solely supporting characters, and too many people don’t allow themselves or get to be the stars in their own stories.

To untangle this no-win scenario, you’re going to need to practice intention, boundaries, and courage. You’re also going to have some hard conversations.

THE SUCCESS VERSUS VIRTUE MYTH

Another version of the no-win scenario is the Success Versus Virtue myth, and there’s a host of variations on this one.

Here are a few different variations on this theme:

The Starving Artist myth . This myth counterpoises creativity, authenticity, or craft with financial success. If your art starts selling well, it means you’ve sold out. So the story goes.

The Nice Guys Finish Last myth. Yes, this is very similar to the previous kind of scenario, but it switches the focus from harming others to harming your own integrity or virtue. Better to be a person of character and not win than be a winner who sacrifices their own character.

The Rich People Are Bad People myth . Rich people, the story goes, have cheated, stolen, oppressed, manipulated, or generally schmucked their way into wealth. That religious and spiritual traditions reinforce this only adds to the truthiness of the story.

In each case, some success state — wealth, achievement, fame, power, influence, etc. — is pitted against some virtue — honesty, generosity, authenticity, creativity, kindness, etc. To have the former, you have to compromise the latter. Or, even worse, if you work your way into having the former, you have to feel guilty or unsettled by it and work harder to make sure you’re being a good person.

JEFF GOINS THE MYTH OF THE STARVING ARTIST

The world usually doesn’t look kindly on those with creative dreams. We give these creative souls all kinds of well-intentioned advice. “Be careful,” we say, even if only in our minds. “Don’t risk too much. Be sure you have a backup plan. Because you could starve.”

What we often forget, though, is the starving artist story is a myth. And like all myths, it has the power to shape our lives — if we believe it. Those of us who believe the myth of the starving artist end up taking safer routes in life. We become lawyers instead of actors, bankers instead of poets, doctors instead of painters. We hedge our bets and hide from our true callings. Nobody wants to struggle, after all, so we keep our passions as hobbies and follow predictable paths toward mediocrity.

But there’s another story worth considering. The story of the thriving artist. What if you could do your best creative work and you didn’t have to starve to do it? What if you could thrive?

In the late Renaissance, artists were often well paid and as a result earned a place among society’s elite. Today, we’re experiencing a similar resurgence of talent — a New Renaissance of sorts — in which creatives of all types are waking up to their potential. They neither have to starve nor sell out. They can thrive. We all can. It just comes down to the story we believe.

Jeff Goins is a writer, speaker, and entrepreneur. He is the bestselling author of five books, including The Art of Work: A Proven Path to Discovering What You Were Meant to Do and Real Artists Don’t Starve: Timeless Strategies for Thriving in the New Creative Age . His award-winning blog, Goins, Writer , is visited by millions of people every year.

It’s true that we have plenty of examples of people who have managed to accrue success at the cost of their integrity. People will sell their soul or others’ bodies for a buck. People will step on other people’s necks to get four inches ahead. People will cut corners while still selling the square.

But there’s no necessary connection between the two. There are plenty of examples of people who are successful and have integrity. There are also plenty of examples of unsuccessful people who lack character.

To extrapolate the journalist and biographer Robert Caro’s point about power, success doesn’t alter your character — it reveals your character. It can also test your character simply because the more successful you become, the more momentous and impactful your choices will become at the same time that more people will want your attention and resources.

To untie this particular no-win scenario, then, requires reframing the tension.

Here are three simple ways to do so:

Who is a model of someone who has managed to be successful and virtuous? Your models will be different from mine, and they can be historical or present. If they were able to do it, why can’t you?

Consider what virtue you think is in jeopardy. What specific actions or behaviors would violate that virtue? Is it necessary to do those actions or behaviors in order for you to be successful?

How might winning or being successful allow you to be more virtuous? Would you be better able to support or engage with what matters most to you?

You’re too creative and resourceful to believe that you can’t be successful and a good person. Yes, be on guard for missteps of character, but don’t assume that you must take them to get ahead.

THE WHAT IF I CAN’T DO IT AGAIN? TRAP

The What If I Can’t Do It Again? no-win scenario is a particularly insidious one for high achievers since we continually find ourselves doing well without much effort and preparation — so much so that we approach projects knowing that we can coast through them. At the same time, we know that there’s a big difference between the results when we actually show up to win versus coasting, but this knowledge and practice ends up working against us. If we really stand tall and are seen for what we can do, we’ll set a high standard that — gulp — we may not be able to do again.

So in order to prevent the second failure, we pick a success level and amount of effort that ensures that we can top ourselves in the future. The convenient upside to this is that we also don’t have to choose what we’ll be truly excellent in. We can continue to dabble, be better than the average bear, and collect our hodgepodge of third-place trophies with the smug, knowing grin of how much harder the people who won first and second place worked to get there.

The reason this no-win scenario is so hard to untie is because deep under the top-line question of “What if I can’t do it again?” is a fear of losing the fun and freedom that comes with being a dabbler and polymath. Mastery and excellence require continual work, failure, and intention — we have to dig in to sweat the details and execution after it’s fun, to get to the different kind of fun and freedom that comes with being an accomplished master of our craft.

Additionally, the What If I Can’t Do It Again? trap overlooks that, along the way, we’ll accrue more experience, people, and resources to do it better next time. Of course, we’ll also escalate our goals and project scope, but that’s what it means to be in that arena. At any given point in our lives, we’re better than we were two months ago. Just as we should assume the sun will rise tomorrow because it rose today, we should also assume that we’ll be two months better two months from now.

So perhaps it’s true that this current version of yourself won’t be able to do it again. Luckily for you, the better, stronger, and wiser version of yourself, playing your best game, will probably be able to do it. Success is cumulative; the shots you take today don’t take from the shots you’ll have in the future — they add to them.

Have the courage and faith that when the next dragon comes, you’ll be able to slay it. Despite what it can sometimes seem, the fact that you’ve made it to here is evidence that you can make it to there.

And you might fail next time around, but better to try something with all your heart that might not work than to continue to go for the easy wins. Do you really need another third-place trophy?

TRANSCEND THE SAFE PLAY OF MEDIOCRITY

Let’s take a look at the two prongs of no-win scenarios the way we’ve been talking about them. Avoiding failure needs no real explanation — no one wants to fail or be embarrassed or humiliated.

But when you have one of the beliefs above about success — that it will cause relational harm, that you’ll have to be less virtuous, or that you’ll eliminate your ability to be free or have fun — then those are some dragons you’ll also want to avoid. The only way to avoid them is to be just successful enough to not risk them. If you stay far enough away from the dragons, they can’t bite you.

The sad truth is that there’s likely a small number of people in your life who will get mad, upset, or frustrated by your mediocrity, especially if your mediocrity is tied to your being attentive to their needs, priorities, or goals.

They will get mad, upset, or frustrated by your failures, and they may get mad, upset, or frustrated by your success.

Thus mediocrity is the safe play. No dragons can bite you, and you won’t create more dragons when you overcome the one in front of you.

Mediocrity being the safe play is only partially true, though. It’s true in the short term and in the day-to-day decisions and compromises you have to make: keep your head down, check the box, avoid the heat today.

But in the long run, it’s the worst thing for your thriving in life and your career. Whose work do you remember that’s a product of their keeping their head down, checking the box, and avoiding the heat? What important change in our culture has come from that? How many kids do you know who are thriving whose parents let them choose easy, safe options?

We’re no more able to thrive by being mediocre than a fish is able to thrive in a shallow puddle. Sure, the fish may survive, but until they connect back with the deep waters and others of their school, they will always be a sunny day away from disaster.

We don’t overcome no-win scenarios by choosing mediocrity; we overcome them by rejecting the stories that create them and doing our best work that creates success, happiness, and character.

SETH GODIN ONLY THE TALL POPPY GETS THE FULL SUNLIGHT

Why choose mediocrity?

After all, it seems more fun to be extraordinary. To search for excellence. To be the one and only, the best in your field.

And yet there’s a lot to be said for mediocre. Mediocre is another word for average. For fitting in. For doing precisely what’s expected of you — pleasing as many people as possible.

Inherent in mediocrity is a degree of safety. The mediocre alternative is the standard one, and if you’re the standard, it’s easy to defend your actions. In every herd of antelope, there are a few outliers, dancing around the forward edges of the herd, teasing the lions. And there are a few at the rear, a little slow, the first to get picked off in the hunt. But the antelope in the middle of the pack is reassured to know that it’s safe, isolated from the rest of the world.

We were taught this pack behavior in school. Middle school is a lot easier to survive if no one notices you, after all. And those lessons stick.

The problem? When our desire to matter collides with our need to feel safe. While being mediocre may feel safe, it no longer is. Because only the exceptional performers earn our attention, only the outliers have room to thrive and grow.

In many cultures there’s the myth of the fate of the tall poppy. They say that it’s the tall poppy that gets cut down, so you better not reach too far. The truth is, though, that it’s only the tall poppy that gets the sunlight, and only the tall poppy that reaches its potential and is able to contribute what it’s capable of.

Seth Godin is the author of nineteen international bestsellers, translated into thirty-six languages, that have changed the way people think about work, among them Unleashing the Ideavirus , Permission Marketing , Purple Cow , Tribes , The Dip , Linchpin , Poke the Box , and All Marketers Are Liars . He writes the most popular marketing blog in the world and speaks to audiences around the world. He is the founder of the altMBA, the founder and former CEO of Squidoo, the former vice president of direct marketing at Yahoo!, and the founder of the pioneering online startup Yoyodyne.

DON’T BE DOWN WITH OPP (OTHER PEOPLE’S PRIORITIES)

If our project and priorities existed in a vacuum, they’d be far easier to get done. While we’d still thrash along the way and have to show up to do our work, we wouldn’t have to manage our inner battles along with others’.

Alas, our priorities and projects exist alongside other people’s priorities and other projects. Other people’s priorities (hereafter OPP) seem similar to competing priorities, but the significant difference between OPP and competing priorities is that competing priorities are about our own accepted priorities rather than other people’s priorities that we accommodate, acknowledge, or accept. If we accept OPP as our own, then they do become competing priorities, at least until we do some internal reflection and realize that there’s value or intention misalignment.

For instance, many people follow pathways that make their parents and family happy. Whether it’s assuming the family business or becoming the praiseworthy doctor or lawyer, many people grind through educational gauntlets, jump through political hoops, and fit themselves into clothes that never hang right because they’re advancing someone else’s priorities. Burnout, red convertibles, and broken hearts are predictable outcomes for pursuing OPP for too long.

Less extreme examples abound in our work and personal lives and at the project level. It could be that your boss’s priorities shift and the project they once were behind gets kicked to the Island of Deprioritized Projects. Your partner’s health and sanity may take a dive and your partner needs additional quality time with you. Your parents’ downsizing project might become a storage problem for you as heaps of random stuff become yours to process.

Here are a few rules of OPP to consider:

The longer your project takes you to complete, the more OPP you’ll have to contend with.

The more important your project is to you, the more OPP you’ll have to contend with.

There will never be a day in which OPP will go away. The world won’t align so that everyone takes their priorities from your plate and makes your priorities their own. Consider how much OPP you end up managing on your birthday; if any day is going to be the day in which OPP subsides, it should be your birthday.

If you aren’t clear about your priorities with yourself and other people, you’ll continually be beset by OPP.

The more you bend and accommodate OPP, the more you’ll have to bend and accommodate OPP.

The rules of OPP and boundaries are heavily interlinked. Maintaining strong boundaries helps sway the daily disruptions of OPP, since you have the right yeses and nos already set up to defer to. If it’s well established that you spend Saturday doing planned adventures with your kids and family, then even if there’s a really good reason for someone to ask you to do something on Saturday, it’s a different conversation than if there’s a history of co-opting you on Saturdays. Similarly, if you have a positive boundary such that you work on creative projects in the morning, people know that you can’t be co-opted in the morning.

Here’s how to address OPP as it comes up during your project:

For OPP that you accept or will accommodate, create the space and time in your schedule to do so . This gives you a “yes and when” response that’s less murky than “I’ll get around to it.” For example, if your dad calls you because he wants to talk, but it’s actually not urgent, you can let him know you’ll call him Wednesday night when you can give him your full attention. If you know that weekly is the right communication pulse with him, creating the positive boundary such that you talk with him every Wednesday may also prevent in-the-moment negotiations.

For OPP that you don’t or can’t accept, be clear that it’s a no rather than a maybe. It’s better to establish this earlier rather than later. If it’s a relationship that matters, you may need to find an acceptable alternative. That said, remember that “no” can be a complete sentence.

For OPP that you can’t authentically accept and also can’t outright reject or renegotiate, your best bet may be to go covert and advance your project in your own personal time. For instance, your boss may not like the fact that you’re working on a side hustle or nonprofit, but they can’t say much if you’re working on it during your lunch break or off-hours. If you go this route, it’s important to avoid any discussion about your project with or in the presence of derailers (more on derailers to follow). If talking to your dad about how your book is coming along derails you, when he asks how your day or week has been, avoid mentioning anything about how your book is coming along, even if it’s been a good week.

CAN YOU WEAVE OPP INTO YOUR PROJECT?

The above strategies assume that there’s a conflict between OPP and your priorities and projects, but it’s often the case that you can weave OPP into your project. The advantage of doing this is that you may be able to add some people to your success pack who may have otherwise been on the sidelines. In many cases, when people are kept on the sidelines of projects that matter to you, they tend to gravitate toward being derailers and naysayers; when they’re on the sidelines, you’re choosing your projects and priorities over them, and people are incredibly sensitive to what appears to be a loss of status. In our attention-starved world, there’s even more of a relationship between attention and status than there has been in the past.

For instance, let’s say you’re working on a project that requires working when your partner wants to focus on her health. Rather than assuming that your partner’s doing their thing and you’re doing yours, there may be a way that you can exercise with your partner while talking out what’s going on with your project.

Or maybe your boss wants you to focus on a different project than the one you’re working on. You may be able to do your boss’s project but in a way that increases the skills, expertise, contacts, or credibility that can be leveraged for your project.

Weaving OPP into your project isn’t always possible, but “How can I weave OPP into my project?” is always a good question to ask. That said, be careful that you don’t accommodate or weave OPP into your project so much that it becomes so unwieldy in scope or so difficult to negotiate that you can’t finish it. As a rule, projects with fewer people involved tend to be finished faster, but projects fueled by more robust success packs are easier to finish.

The above strategies for handling OPP address the people in your life who are generally supportive of you and what you’re working on. Alas, these strategies are inadequate for your derailers and naysayers. We’ll turn to them next.

DERAILERS AND NAYSAYERS

If your success pack is the rocket fuel that propels your project, your derailers and naysayers are the winds actively working against you. Not every project has them, but the more your project challenges the status quo, the more likely it is that you’ll have some derailers and naysayers. Someone benefits from status quo, and they rarely relinquish those benefits without a strong protest or fight.

But the fact that they work against you doesn’t mean that derailers and naysayers are the same thing: derailers are sometimes well-meaning people whose “help” and “feedback” throw you off course, while naysayers are people who are actively against you and your project. It’s the difference between a dog that gets too excited and bites you versus a dog that’s a biter; the end result is that you’re bitten, sure, but you may be able to enjoy being around the too-excited biter.

HOW TO HANDLE DERAILERS

The most challenging thing about derailers is that they often don’t know they’re derailers. From their perspective, they’re trying to help and want you to be successful. From your perspective, you either have to armor up to interact with them or emotionally reset after talking to them.

Your derailer could be your mom, an editor by trade, who proofreads and corrects your online writing without asking. It could be your partner who’s the frugal one in your relationship that questions and critiques every purchase you make or are even thinking about making. It could be your uber-successful sibling who thinks your idea is an adorable pet project but isn’t worth taking too seriously. In a professional context, it could be an overly critical boss who expects you to have a fully formed idea before you talk to them about it or the “devil’s advocate” guy who picks apart your idea without ever evaluating and praising its merits.

Assuming that your derailers are well-meaning and want you to be successful, here’s how to go about interacting with them:

Confirm that they want you to be successful with your project . Sometimes a simple “Hey, I sometimes get the feeling that you don’t want me to be successful with this project or idea” is enough to start a good conversation. It’s typically not useful for you to have an exhaustive catalogue of the ways they’ve derailed you, but listing general themes (as I did above) is helpful. In a professional context, you may need to cloak the request as a collaboration technique to depersonalize it. The end goal of this conversation is to get buy-in confirmation and an agreement to try a different way of interacting.

Request the type of feedback or partnership you’re looking for . If you need your partner to not critique every purchase for the next few months, put that on the table. If you want the “devil’s advocate” guy to evaluate the merits of your idea first, then request that. What rarely works is doing what they do to you back to them; they’re better at it than you are, and it may signal that that’s how you want to interact. Plus, being passive-aggressive is never a good look.

If they continue to do their derailing thing, don’t vote them off the island or put them in the naysayer camp yet. Remind them of their agreement to try a different approach or “collaboration technique.” Your request is likely interrupting deeply ingrained habits or unconscious patterns. Try a three-strike rule before you move to the next strategy.

If they continue to do their derailing thing, your second fallback is to be more strategic about when you have conversations with them. For instance, it may be better to talk to your fully-formed-idea-first boss after you’ve run it past your success pack; in this case, you’re more likely to get praise for such a well-thought-out idea than criticism for a half-baked idea.

If they continue to derail you after step 4, then follow the suggestion I gave for dealing with OPP you can’t accept or reject: do your project covertly and avoid talking about it anymore . People get tripped up here because they want to celebrate progress or accidentally slip into discussing setbacks vis-à-vis the covert project, but that’s the door for the derailer to walk through. If the derailer specifically asks how the project is going, a generic “good” or “it’s coming along” is your best bet, even if it’s not going well. The only exception to this is in the (very) off chance that their derailing pattern is actually what will help you get unstuck.

I’m fully aware that the steps above look like a lot of work and, yes, it will require courage to have some of the conversations. The payoff is in line with the fact that learning to include rather than sidestep your derailers removes some of the active force against you and your project as well as potentially upgrades them to success pack members.

HOW TO DEAL WITH NAYSAYERS

Naysayers remind me of the parable of the scorpion and the frog. In case you’ve never heard of it, the scorpion asks the frog to ferry him across the pond. The frog objects, claiming that the scorpion will sting him. But the scorpion replies that it would make no sense to sting the frog. The frog, seeing the reason in the scorpion’s argument, relents and lets the scorpion on his back. Midway across the lake, the scorpion stings the frog and, before they both drown, the frog asks why the scorpion stung him. The scorpion’s response: “It’s in my nature to sting.”

For whatever reason, it’s the nature of a naysayer to naysay. Singer-songwriter Taylor Swift had it right that “haters gonna hate.” Some people are equal-opportunity naysayers and put down everything equally. Some people’s naysaying is particular to their relationship with you. Others may feel a responsibility and see their naysaying as vocally and proactively asserting standards.

It’s rare that the one naysayer in a thousand people will bear any weight on your success unless you overfocus on them. The exception, of course, is when a naysayer is part of the much smaller circle of people who can approve, reject, or tank your project. If one of your naysayers is on your dissertation committee, that’s a real problem. Similarly, if your boss or boss’s boss is a naysayer, that’s a real problem. In the former case, you need to get them off your committee, and, in the latter, you’ve got to win them over (unlikely) or get out of their chain (probable). 1

JEFFREY DAVIS LET WONDER INTERVENE WITH DERAILERS

It takes .5 seconds from the moment your brain receives unwanted input to the moment you close down or armor up.

But a Wonder Intervention can trip your wiring and open you up to opportunity. A Wonder Intervention is an evidence-based practice that brings more openness and purpose to our work and relationships.

To discover opportunity in a derailer’s input, try this:

Observe and reverse. Before you react, recalibrate. Rub your temples. Repeat to yourself, “Open up instead of size up.” Doing so reverses the closed state both in mind and body.

Normalize instead of pathologize . Observe your reaction as a common biological defense and refrain from internal storytelling about the other person or your project. Say something clear and curious to yourself such as, “That’s an interesting reaction.” No obsessing, please.

Open to collaborative input. Ask the person a clarifying question such as, “What prompted your input?” Or “Could you elaborate on X?” Ask them a more open-ended question that could elicit their genuine curiosity versus criticism: “Could you see the project this way?” “What if X happened?”

Listen with your feet. Drop awareness to your feet. This prompt lets you receive without defense. Doing so has helped numerous managers, startup founders, creatives, and team players forge wholly different, more productive relationships on behalf of projects greater than their egos.

You would be surprised by what could happen. The derailer suddenly could become an ally, advocate, and ambassador for your project because you shifted the dynamic. It’s possible.

Jeffrey Davis is CEO of Tracking Wonder, a consulting firm that equips creatives, leaders, and organizations to brand with integrity. The Wonder Interventions at Work programs help entrepreneurs as well as teams override implicit biases, boost daily creative problem-solving, and foster more open workplaces. A speaker and author of four books, Jeffrey writes for outlets such as Psychology Today.

Fortunately it’s relatively rare to have a personal naysayer who has that much power over you and your project. What’s far more common are the ghost naysayers that we turn into dragons. The only way to beat these kinds of dragons is to realize that they’re illusions and projections.

Think about your chosen project. If you’ve sat with it long enough, you’ve probably generated some naysayers. The naysayers that are easiest to dismiss are the ones that take some form of anonymous people “out there” (on the internet, in your city, in some cubicle in a galaxy far, far away). If you can’t replace the “they” in “What if they don’t like it?” with a real name, you’ve got ghost naysayers. (Try it.)

The second kind of naysayers are actual people who have responded to you or your work. These naysayers are likely people from your past, such as that fifth-grade teacher who embarrassed you by critiquing your writing, or Jimmy from eighth grade who teased you when you couldn’t climb the rope. Past naysayers are ghost naysayers at this point; the only power they currently have is what you give them.

When you see ghost naysayers for what they truly are — your own head trash — you’re not likely to have many real naysayers to contend with. But in the case where you have real naysayers, here’s what to do:

Don’t engage with them. No matter what you do and what they say, you’ll end up stung and drowning.

Stop trying to make them happy or alter your project to meet their approval. The worst case is that you actually do so, because now you’re beholden to pleasing a naysayer and have probably done so by dismissing or neglecting your yaysayers.

When you have the urge to engage with a naysayer, engage with a yaysayer instead. They’re in your success pack and probably all around you.

In the extremely unlikely case that a naysayer ceases their active naysaying, do not think that they’ve joined your success pack and you’re now BFFs. They’ve now been promoted to derailer, at best. Better yet, focus on your yaysayers and success pack, since that’s probably what led to you getting the naysayer’s approval anyway.

The hardest naysayers to deal with will be people from your nuclear birth family, as you’re literally bound to them by blood. Few things cut as deep as naysayer-level rejection by your parents or siblings. The strategies above are just as valid for family naysayers as any other, with the only alteration to the strategies being in the first: don’t engage with them about your work. Thanksgiving dinner isn’t the time or place to defend your project or work. Follow the covert project strategy as well.

Every ounce of energy you use grappling with a naysayer is much better spent on working on your project and interacting with your success pack.

Choose the people who have got your back, not those who never will.

HOW TO DO A PROJECT PREMORTEM

How many times have you sat through a meeting or conversation where you discussed what led to a project going sideways or into the gutter and thought to yourself, “It would’ve been nice if we had talked about this before we kicked off the project”? Or how many times have you realized midproject that, if you had taken a second to think about it, you probably could have avoided or planned for whatever you’re now bumping up against?

A project premortem is the process of considering all the ways that a project might go south so you can actively work to prevent those things. Doing a premortem doesn’t assume that the project is going to die but rather that every project will have some challenges along the way. Known, planned-for challenges don’t tank projects; surprises and willful insanity — repeatedly doing the same thing while expecting that this time it’s not going to trip you up — do. The converse is true: failing to do the things you know work and wondering why you’re struggling is also willful insanity.

Now that you know the universal kinds of drag points and hopefully see that you’re not somehow uniquely defective because they plague you, you can make a checklist to walk through your premortem. You neither have to recreate the wheel nor repeatedly climb out of the same hole. Huzzah!

You’re doing a premortem at this point because you may need to alter the timeline based on drag points that are likely to come up. For instance, if you accidentally put a derailer in your success pack — it’s really easy to do — subbing them out for someone who’s more supportive or placing them later in the process may alter how long something will take. If you baked in OPP in your estimate as to how long something would take but now see that you may be able to co-opt the person, you may alter the timeline or build in some additional time because, while it may take longer to do, best-work projects are better with friends and loved ones.

Let’s return to your project. Though we’ve been discussing drag points and ways your project can go sideways on you, let’s refocus on the fact that you’ve picked an idea that matters to you, converted that idea into a SMART goal, and assembled a success pack that will help you stay on course. You already have what it takes to be successful, and what you might lack now you can acquire on the journey. (It’s important to do premortems from a grounded, resilient, and positive perspective.)

Now use the following questions to do your project premortem:

Have you created any no-win scenarios for yourself? How might you detangle them?

Have you picked a method of doing your project that’s especially hard for you? How might you start from and leverage your GATES?

What OPP do you need to account for? How might you align OPP with your project?

Are there any derailers and (real) naysayers you need to account for? List them by name and how you’ll address them.

Are you carrying any projects that you can let go of to keep them from bogging you down?

Are there any bad or unhelpful stories you’re telling yourself — you’re a flake, you’re not good at planning, who are you to think you can do it, and others — and what will you do to counteract those stories?

If you’re honestly engaging with the questions above, you’re likely to have a range of emotions that vacillate between feeling daunted to feeling eager to overcome your drag points. If you’re mostly feeling daunted and overwhelmed, great! Sit with it and return to your premortem after a few days, as you’ll likely have generated some solutions and breakthroughs when you return. If you’re mostly feeling eager to overcome your drag points, great! Do a metaphorical victory lap and know that we’re going to get nitty-gritty in the next chapter about getting your project on your schedule.

CHAPTER 7 TAKEAWAYS

Drag points are the natural places where reality will push against your plans.

There are three kinds of no-win scenarios we often tell ourselves: the Success Will Wreck My Relationships tale, the Success Versus Virtue myth, and the What If I Can’t Do It Again? trap.

We choose mediocrity (in the short term) because we don’t want to succeed due to the no-win scenarios but we also don’t want to fail — mediocrity is the space between success and failure.

OPP (other people’s priorities) create conflict with our best work, but there are often ways to weave OPP into our work and convert conflict into cooperation.

Derailers are well-meaning people whose “help” and “feedback” throw you off course; naysayers are people who are actively against you and your project.

Project premortems help identify and avoid the challenges that may kill or slow your projects.