Business & Economics

Start Finishing: How to Go from Idea to Done

By Charlie Gilkey

This book will launch on Nov 29, 2019. Currently, only those with the link can see it.đź”’
Synopsis

How much of your time and attention lately has been focused on things that truly matter to you?

Most people's honest answer is: not enough.

Everyone is buried by busywork, responsibility, distraction, and fatigue.

The joy-producing, difference-making ideas are waiting for when the time is right, when the current project is over, when they have a little more money, when the kids are grown, or when they get a more understanding boss. They are waiting for someday.

The trouble is someday never comes on its own.

Start Finishing presents a 9-step method for converting an idea into a project by addressing the challenges you'll face and getting the project on a reality-based schedule.

You are not incapable, wired to struggle, or fated to be unable to get your act together. With a few key steps, you can change the way you show up, how you plan, and how you respond when things get tough.

You can Start Finishing the work that matters most to you.

Includes original contributions from Seth Godin, Susan Piver, Jonathan Fields, James Clear, and many other teachers.

PICK AN IDEA THAT MATTERS TO YOU

The day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.
–ELIZABETH APPELL, in a promotional pamphlet for John F. Kennedy University, 1979


We’re paradoxical creatures. On the one hand, we all want to do our best work. On the other hand, we often avoid doing it.

This paradox only makes sense when we acknowledge that there’s a lot happening in our inner landscapes that’s keeping us from choosing to do our best work—and that makes choosing an idea that matters tricky. Unfortunately, with all the meetings, commutes, notifications, and things to do, we’re not often privy to everything that’s happening inside our hearts and minds.

What we can often see is that we’re doing a lot of work around our best work but not getting anywhere with it. Hours, days, and weeks can go by with us researching, mulling, procrastinating, and touching our best work just enough to keep it warm but not enough to push it along.

To pick an idea that matters, the part of you that wants to thrive and do your best work will have to overcome the part of you that wants to play it safe, be comfortable, and not ruffle any feathers. It’s time to embrace the thrashing you’re doing.


THE MORE IT MATTERS, THE MORE YOU’LL THRASH


Thrashing is the term I use for this emotional flailing and metawork we do when we don’t fully commit to our best work. What’s really going on is that we’re working out our own head trash—the fears, impostor syndrome, and (sometimes) unconscious perceptions of our own inadequacies. When we’re thrashing, we’re like the rocking chair that moves a lot but doesn’t actually get anywhere.

But generating all that motion can be more exhausting than actually making progress. Even worse, at some level, we know we’re thrashing and can’t figure out why.

Here’s the thing, though: we don’t thrash about taking out the trash or doing the dishes. We don’t have an existential crisis of varying degrees of intensity when it’s time to cook dinner or go to the library. (Though if you’re anything like me, having to decide which books won’t be going home with you can invoke a mini crisis.)

If you’re familiar with Steven Pressfield’s notion of resistance, you might think that thrashing and resistance are the same thing. They’re not. Resistance is the inner voice or actor that’s often the mouthpiece for all the head trash we carry with us.

Thrashing is what we do in response to resistance.

That may seem like a minor difference, but what I find useful in the distinction is that we can notice when we’re thrashing and decide that we’re going to do something different, even as the resistance yells at us ever more loudly and forcefully. Additionally, knowing about thrashing allows us to tell others what thrashing looks like for us so they can call us on it, rather than leave it for them to guess what’s going on inside our head and heart.

We only thrash about the things that matter to us: getting married for the first (or third) time; leaving a comfortable job to start our own business; writing a book; starting a nonprofit; doing an open-mic event; sharing our art with a new audience; kicking off a disruptive strategic project. Each of these can get us thrashing, and many people never actually get beyond thrashing.


The more an idea matters to you, the more you’ll thrash, precisely because its success or failure is deeply important to you.


While most of us don’t care about how perfectly aligned our trash cans are when we put them out on the curb, we do care about how perfectly presented our best work is. Our best work is a representation of our internal character, competency, and excellence in a way that the curbside trash cans aren’t. (At least, that’s the story we tell ourselves.)

Every project that matters to us will entail some thrashing, but where we’ll thrash is often quite particular to us.


Some of us thrash:


• Before we start working on an idea. “Who am I to do this project?” “Does this project even matter?” “Is this original enough?” “Can I actually do this?”


• In the middle of the project. “How the hell do I get this project back on track?” “Why is this project so hard for me?” “Is anyone even going to care if I finish this?” “Is this really the best thing I can be doing right now?”


• At the end of the project. “Is this good enough?” “What will people think of me?” “What about the haters, trolls, and naysayers?” “What if I miss something important?”


• Throughout every stage of a project. We’re masters of the flailathon.


A natural response to thrashing is to pick easier ideas to work on. Sheer exhaustion, frustration, and the desire to actually get something done make switching projects seem like a good idea. Ain’t nobody got time to wear themselves out for half of the day and not have anything to show for it.

You’re most likely to start reaching for an easier project when your project goes into a void. When your project is in a void, it can seem like it can keep going nowhere forever and there’s not a clear way to get the project out of the void. Best-work projects are particularly prone to have one or more voids, which is yet another reason they too easily get pushed to the side for an easier project.

Beware the siren call of the “easier” idea, though. If you switch to an easier project that matters, you’ll end up thrashing anyway, and it will probably be in about the same spot as the current project you’re thrashing with.

It’s not like switching to an easier project automagically means you’ve addressed what caused you to thrash with your previous one. And if it’s an easier project, you might finish it, but you won’t feel nearly as satisfied as if you had finished the one you bailed on. And you’ll still be haunted by whatever undone project you switched from.

Thrashing is thus not a sign that you can’t finish the project or that you’re doing the wrong project. It’s a sign that you’re doing something that matters to you and that you’ll need to show up powerfully to get it done. It’s also not something you’ll ever get away from—as you become more powerful and accomplished, the ideas you’ll grapple with will scale with you, in scope, breadth, or difficulty.


AVOIDING YOUR BEST WORK LEADS TO CREATIVE CONSTIPATION


Your best work is always going to be challenging because it’s the work that matters to you. And because it matters to you, you’re going to be thrashing along the way. Best work is starting to look suspiciously like hard work, and our natural reaction is to avoid doing hard work and to instead find something easier to do.

When it comes to your best work, not doing it comes with two major costs: (1) you won’t be able to thrive, and (2) you’ll be stricken with creative constipation. Since I’ve already discussed the link between thriving and your best work, let’s talk about creative constipation, or the pain of not doing your best work.

Creative constipation is exactly what it sounds like.

We take in ideas and inspiration that get converted into aspirations, goals, and projects, and at a certain point, if we’re not pushing them out in the form of finished projects, they start to back up on us.

And like physical constipation, at a certain point, we get toxic. We don’t want to take in any more ideas. We don’t want to do any more projects. We don’t want to set any more goals or plans. We’re full and fed up.

That inner toxicity becomes the broth that flavors all our stories about ourselves and the world; our head trash gets more pronounced and intense, and what we see in the world goes from bright to dark. Creative constipation leads to behaviors in which we lash out at the world—and sometimes even more intensely at ourselves. We become resentful of others—even people we love—who are doing their best work.

Our ability to feel positive emotional peaks is diminished at the same time that our ability to feel negative emotional troughs is amplified. You’ve no doubt encountered the tortured, depressed soul who’s creatively constipated—and you may have been there yourself.

There’s a reason that nearly every spiritual tradition links creativity and destruction: the same energy that fuels creation also fuels destruction. The Jewish, Christian, and Muslim God creates and destroys; “beating swords into plowshares” works equally in reverse. The Hindu god Shiva is seen as a destroyer who makes way for creativity. Creativity and destruction are seen as a continual loop in the Taoist concept of yin and yang.

Spiritual insights such as these also show up in our everyday lives. Think about how often you’ve engaged in retail therapy—and thus destroyed your time and resources—because you’re unsatisfied about something in your life. Think about how often you’ve indulged in emotional eating because you’re not creating the change you want to see in your life. Think about how many people blow up their lives in a midlife crisis because the career and life they’ve made haven’t satisfied their deep needs.

Now think about the people you know or have read about who are doing their best work. Notice how they’re healthier, happier, (usually) more financially comfortable, and in good relationships with others? Doing their best work creates meaning for them at the same time that it cocreates who they want to be in the world. And these folks know that doing their work in the world is the wheel of change, meaning, and growth, more so than merely being stuck in their heads.

So at both deep and practical levels, we can choose to channel our energy to do our best work and thrive, or we can choose to leave it unharnessed to gradually destroy ourselves, our relationships, our resources, and the world around us.

Better to do the hard work of creation than the hard work of repairing the destruction we’ve wrought.


WE ARE MADE TO SLAY DRAGONS


Your best work is hard work during which you’ll thrash, and if you don’t do the work, you’ll be feeling a different kind of pain. “There be dragons” on the journey to thriving and doing your best work. You can avoid some of the dragons—especially the ones you create for yourself—but you shouldn’t expect to avoid all of them.

It’s far better to be skeptical about doing the easy work or always picking the low-hanging fruit. Too many of us wake up after doing years of work that doesn’t stretch us or make us really show up to do it, and we realize that we’ve been phoning it in. Easy work can be like fast food: it’s quick, easy, and cheap, but it’s not fulfilling and too much of it can lead to dis-ease.

But here’s the deal: we are made to slay dragons. We have survived for hundreds of thousands of years using our creativity, grit, imagination, and cooperative spirit. We’ve harnessed fire and metal and the very energy of the universe to alter reality. We’ve survived countless plagues, wars, and famines. Physically, we’re the weakest and least capable of every predator and yet we’re the apex predator on this planet.


We’re simply the latest in the line of generations of dragon slayers. We’re resilient, adaptable, ingenious, and triumphant folk.


So what if there are a few dragons on this journey? They have always been there and likely always will be there. Lesser people than us have tussled with them and won, and we can too.

Dragons aren’t a signal that we’re on the wrong road but rather that we’re on the right road. So the next time you’re dismayed or hesitant because of a dragon guarding the way forward, embrace that it’s there precisely because it’s the way forward and charge headlong at it. You were made to beat dragons.


THE GIFT OF FAILURE


You may be made to slay dragons, but it doesn’t mean you’ll always be able to do so. Failure is inevitable, and if you’re not failing and making the occasional bad decision, you’re not doing your best work. Really showing up and dancing with the uncertainty that comes with doing your best work means you’re going to underestimate, underprioritize, and underprepare for a challenge that then gets the best of you.

But failure isn’t a mark of character but rather a sign that something was out of alignment. Maybe you . . .


• Charged ahead by yourself rather than asking for help.


• Said yes too quickly when you were already overcommitted.


• Had a streak of easy wins that unlocked a new level of challenge that you weren’t ready for.


• Chose an idea that didn’t match your actual priorities, and the projects that relate to your priorities won out.


• Put the wrong people on your team for the wrong reasons.


• Needed to spend more time honing your skills or collecting your resources.


• Had a beautiful plan that reality shattered in wonderful or terrible ways you couldn’t anticipate.


Your past failures are in the past. They aren’t predictive of what you’ll be able to do in the future. Your best bet is to follow this Cherokee proverb: don’t let yesterday eat up too much of today.

But that’s not to say the sting of failure isn’t real. A corollary of “the more it matters, the more you’ll thrash” is that the more it matters to you, the more it will sting when you fail. This truth is another reason we choose to avoid our best work.


Chelsea Dinsmore: What to Do When Life Changes Your Plans

There are many things in life out of our control, and when life changes our plans it’s hard not to feel helpless. I learned this the hard way when my husband, Scott, was killed in an accident while we were hiking Mount Kilimanjaro. Not only was I having to process this sudden and tragic loss but I was also doing it in front of the global community we had built. What happened was out of my control, but my response to it was not.
This is why I encourage people to have a practice that allows them to intentionally respond rather than simply react to any given situation. We must first accept that what happens around us isn’t what dictates our feelings; it’s our thoughts that create them.
We go in and out of emotions based on our thoughts, which often come as a result of what we focus on. Our circumstances may be facts, but our emotions are fleeting—focusing on what we can’t do creates hopelessness; focusing on what we can do creates motivation.
When we begin to notice the thoughts that create painful and pleasurable emotions, we reveal patterns, understand triggers, and gain insight into where we can better direct our focus in any given moment. The better we can learn to manage our minds, rather than react to them, the better we can handle any situation, regardless of the level of difficulty.
This is a power no circumstance can take away from you!

–Chelsea Dinsmore is the owner of Live Your Legend, a business that helps people discover how to live their lives with a deeper sense of purpose, meaning, and mindfulness.


The gift of failure is that it reveals what matters to you, shows you when you’re out of alignment, and reveals a growth edge.


Each day is a new day to try again with the lessons of yesterday as a guide, not a straitjacket.

Failure is thus like that friend who tells you what you need to hear rather than what you want to hear. But it’s not the only friend keeping you on your game.


DISPLACEMENT IS YOUR FRIEND (AFTER IT’S YOUR ENEMY)


One of the biggest dragons seems to be time. There’s never enough, and we don’t get it back.

The more years I spend on this planet, the more I see that we need the constraint of finite time for the meaning making that matters the most to us. That constraint creates displacement, and taking displacement seriously allows us to make better choices. Displacement is simply the reality that every action we choose to do displaces countless others we could have done in the same space and time.

That’s all very general and spiritual, I know. To make it more concrete, let’s consider Whole Earth Catalog creator Stewart Brand’s idea that significant, impactful ideas will require at least five years of focused action to complete.(1) Subtract your current age from eighty-five and divide by five—that’s how many significant projects you have left to do.

By the time this book is published, I’ll be cresting forty, so that means I have nine significant projects left. That’s only so many nonprofit boards I can serve on, pillars of my body of work that I can build, ways I can serve my community and nation, and places I might move to and truly experience. Yes, knowing I only have nine buckets to pour my life energy into feels like the universe is sitting on my chest. But it also makes me extra discerning about what significant projects I choose to do and how my days go toward those projects.

No matter how we choose to spend our hours, we each get twenty-four of them each day. That finite limit is a hellish constraint for many of us.

But that finite limit can be a gift of heaven just the same. Consider how much more we waste when we have more to waste. How many times have you looked back over a day or week that had too much unplanned time and been frustrated that you squandered that time precisely because it was too open? Or how many times have you clicked over to Facebook because you were bored—that is, you had open time where you weren’t engaged?

Another major gift of displacement is that it can help you assess the cost of being spread across too many projects and responsibilities. For example, I’d like to write more than one book every five years, but to do so, I’ll have to do like other prolific authors and cut more things out of my life to do so. If I decide to cut or not take on something that consumes ten hours per week, I could then apply those ten hours to a book. In that scenario, I’d be able to write one book a year pretty easily. There’s even a helpful constraint there as well, in that there’s only so much creative energy available per day and it’s far less than many people think.

We could quibble about whether Brand’s correct about impactful ideas taking five years to complete or what counts as a significant project, but doing so wouldn’t change the fact that we have a finite amount of time and whatever we do in that time displaces other things we might do.

As you get better at using the five keys and focusing on your best work, displacement will become an even better friend. When stuff that really doesn’t matter and isn’t worth your time, energy, and attention shows up, you’ll feel it right away, and you’ll also feel the potential cost of letting your current project go. We’re wired to feel the pain of loss more than the pleasure of possible gains. Losing the grip and momentum you’re currently building will make it easier to wick away the drops of nonmeaningful stuff as if it were water on a rain jacket. Your fear of missing out (FOMO) will shift from missing out on what other people are doing to missing out on what you could be doing with time well used.

But in the beginning you’ll fight and thrash against displacement. That’s just the infinite part of yourself straining against its bindings. Part of the struggle of the human condition is being an unlimited sentience trapped in a limited body; part of the beauty of the human condition is being an unlimited sentience that gets to use its power through space and time.

I’m highlighting this tension with displacement because we’re heading toward a choice that will catalyze that tension. At the end of this chapter I’ll ask you to pick one idea to start working on and to use it as the lens to understand the ideas ahead. You’ll likely struggle with choosing, and a major part of that struggle may be resistance to the premise that you have to or should choose.


When that time and struggle come, remember these three things:


• Everything you do displaces something else you could have done.


• The work that really matters will require a concerted amount of time to finish.


• The more you channel your energy toward one project, the faster you’ll finish it and therefore can move on to the next project.


Not choosing is a choice that costs you far more in the long run than choosing and finishing one significant project at a time. We can’t run away from displacement, but we can use it to start finishing our best work.


TO TRADE UP, YOU HAVE TO LET GO


While we’re on displacement, it’s useful to think about all the ideas and projects you’re carrying and what they’re displacing. You’re currently carrying a mixed bag of projects and responsibilities, the majority of which aren’t related to your best work or the activities and ideas that are most going to move you toward thriving. The minority of stuff that’s close- ish to your best work is likely stagnant, existing in the same progress status as that closet you stuff full of things you don’t want to process right now but can’t outright get rid of.

I’m not judging. As I’ve been saying all along, it’s far too easy for stuff that doesn’t matter to end up on your to-do list while the stuff that does matter languishes as you wait for days where you won’t have the rest of the stuff to do. Those days are coming, we all swear, despite the lifelong evidence that they won’t.

While we will begin to eliminate some of the work that doesn’t matter, we’ll need to start with that closet of ideas and projects we really want to do. This may seem like a counterintuitive place to start. Wouldn’t starting with the bigger list of stuff that doesn’t matter as much give the biggest bang for the buck? After all, if it’s 80 percent of where our time is going, and we remove 25 percent of it, then we can apply that time, energy, and attention to the stuff in the closet, right?

Probably not, for two reasons. First, the stuff that’s currently on our list is there for a reason, and if it were so easy to let go of, we would have done it already. We either had it imposed upon us or we accepted it at some point in the past. In either case, it has some energy and story attached to it, and it will take some active effort to dissipate the energy and rewrite the story.

The second reason why it’s unlikely that we’ll automagically start doing our best work is because our existing pattern is to fill the space with stuff that doesn’t matter as much. If you’re a people-pleaser, you’re more likely to fill that space with stuff that “pays off” the people- pleasing you haven’t been doing because you’ve been too busy. If you’re a perfectionist, you’re more likely to go about shoring up something you feel you half-did in the past, regardless of whether it’s still alive or not.

If we don’t consciously make the effort to change things, our default habits and patterns will keep filling the holes we make. We have to start by filling those holes with work that does matter. This is how displacement can be a gift. We can put something that’s harder to displace in those cracks and holes, and, with practice, we can replace the go-to chicken wire and duct tape of ephemera with the more solid brick and mortar of our best work.

But to get some headway with your best work, you have to fight the natural inclination to work on all the things you’ve hidden away in that closet. That road ends with your being unsatisfied by your lack of progress and focus, with a strong possibility that you’ll just shove even more undone stuff back in the closet. You’ve probably walked this road before and don’t want to walk it again.

Instead, you must decide from the get-go that you’re just going to let some of those ideas go.


The best way to finish something is often to just drop it, midstream and undone, even while feeling the sting of remorse, regret, and sadness of not seeing it through.


And let’s not pretend as if the choice of letting some of those projects and ideas go is primarily a mental activity. It’s an emotional activity—your soul, emotions, and creative energy are tied up in those ideas. Sometimes there’s money and social skin in the game as well, and none of us want to walk away from money we’ve sunk into something or feel the shame of not seeing our commitments through. Better to hold on to them, as you might get around to them someday.

This reminds me of my dad, a brilliant and industrious jack-of-all-trades. Dad would often salvage things from the construction sites and jobs he worked on because he was “fixin’ to” use them on some unspecified project he was going to work on. He’d kept almost every vehicle he ever owned because he was “fixin’ to” fix them up and use them. He’s going on eighty and currently has dementia, and my siblings and I are left with over an acre of stuff collected over the last sixty years that Dad never could let go of because he just knew someday all that “fixin’ to” would turn into something he actually did. Even now, on bad days, he thinks about all that stuff and how he’s going to get to those projects. How much of his soul is tied up in things he’ll never get to?

My father is a product of his time, when physical stuff was what was collected in order to build real stuff in the world. In the near eighty years since he was born, our society has shifted from atoms to bits—to use entrepreneur, TED Conference curator, and author Chris Anderson’s phraseology.(2) More of us work in intangibles, including services, than in tangibles anymore. We don’t have an acre of unprocessed stuff, but we have the same analogous amount of space in our souls occupied with things we’re “fixin’ to” get to.

In the next section, I’ll be asking you to pick one idea or project to work on or use as an anchor to apply the insights from this book. But in this section I’m asking you to pick some ideas that you won’t be working on anymore so you can free up that energy to fuel what you do work on. It’s a hard ask now, but it will make the next exercise easier because you’ll be working with a shorter list.

So let’s start to unpack that closet of ideas and projects.

Here’s how I suggest doing this:


• Give yourself two uninterrupted hours for this exercise.


• Do it somewhere other than where you work most of the time. Coffee shops and libraries are particularly good settings.


• Use a pencil and paper. Use a pencil so you can erase when you need to—and you’ll need to. Use paper so you don’t collapse into fiddling with technology and checking stuff that doesn’t need to be checked right now. Mindmapping can be more useful than a linear list, but this is not the time to learn how to mindmap if you’re not familiar with the process.


• List all of the ideas and projects you want to do. Think beyond “professional” ideas and projects—yard and house projects, community initiatives, events with your community, traveling to Nepal, sorting your finances, or getting a puppy all count. It can be items on your bucket list, but they don’t have to be bucket-list level.


Once you have this list, start asking yourself the following questions and put an asterisk behind items that meet the criteria of the questions:


1. Which of the items wouldn’t actually hurt at all if you cut them? Be on the lookout for projects and ideas that some previous version of yourself put there that aren’t relevant for where you are right now. For instance, this could be a degree or certificate to get a job you no longer want or that you already have. It could be a creative project that past-you desperately needed to prove yourself that current-you no longer needs because you’re no longer seeking approval.


2. Which of the items would you feel relieved to no longer be carrying? Pay more attention to how it will feel once it’s no longer on your plate than to what you would need to do to let go of it.


3. Which of the items are “shoulds” or items that relate to OPP (other people’s priorities), but you don’t see how they’ll directly lead to your thriving?


4. Which of the items are good ideas but don’t relate to something that frustrates, annoys, angers, inspires, nourishes, or calls to you? You can’t build the flame to temper your project from a good idea that doesn’t have an emotional spark to start with.


Susan Piver Should You Break Up with Your Idea?

Conventional wisdom says that success is dependent on your intelligence, skill,
drive, connections, and resilience. Should you encounter obstacles, just work harder. When things seem hopeless, hustle more. Eventually your idea is bound to work.
But this is simply not true. There’s something missing from this view.
Obstacles aren’t merely stumbling blocks to be gotten around; they’re a source of wisdom. Sometimes the wisdom shows you a better way, but sometimes—and this can be very hard to accept—the wisdom is telling you to stop. Give up. Move on.
How do you know when you should push harder or let go? To discover the answer, it’s useful to take yourself out of the center of the equation. We all think our work is about us and our talents and aspirations. It turns out that this is only partially true, because in order for your project or idea to work, it has to, at some point, spark. A relationship with the world—whether that world is the consumer marketplace, a business sector, or a single client—has to arise.
Ideas are like blind dates. Either may appear perfect on paper—smart, interesting, and attractive—but if there’s no chemistry, it won’t work. You can go out on a million more dates, but that will never change. It’s a matter of history, timing, and the mysteries of destiny. What looks good on the surface is only the beginning.
When the world falls in love with your work, you’ll know it. In the meantime, stay strong and confident in yourself, but develop the capacity to read the signs clearly, respond fearlessly, and remain open to what comes next. It may be better than you ever dreamed.

–Susan Piver is a Buddhist teacher and the New York Times bestselling author of nine books. She is founder of the Open Heart Project, the largest virtual mindfulness community in the world.


If you really engage with the questions, you’ll be able to eliminate a lot of items from your list. How many depends on how long you’ve crammed stuff in that closet without purging it. If you’re a frequent purger, you may have a short list. If it’s been a while, you may have a long list.

Now the important part:


eliminate those items rather than defer

and put them back in the closet later.


Whenever that later comes, they’d be asterisked all over again. You’ve done the hard work of making the evaluation once—don’t do it again.

Some people find it helpful to do a send-off process for each item. Think about the item, how you came to it, how it’s helped you, and how sending it off will open up more energy for something that’s relevant now. A simpler process would be to say something such as “I release you” or “we’re complete.” Burning the list has been particularly cathartic for me and others I’ve led through a similar process. How you do it is less important than making the clean, intentional break.

Now that you’ve let go of stuff that matters less, you can trade up to what matters more. To prep for that, rewrite the list you started with so that it only includes ideas and projects that made the cut. For the projects you’ve let go, there’s no need to see them anymore.


FIVE QUESTIONS TO HELP YOU SORT THROUGH WHAT MATTERS MOST


If you did the exercise above, you may have been surprised to see that what you originally thought was important to you really wasn’t, and what you pushed aside as unimportant really was. If you’ve experienced a roller coaster of emotions, great—that means you’ve been open and honest with yourself. You’re right where you should be.

Much as we learn to live by living, we learn to do our best work by doing our best work. And the best way to do our best work is to pick a specific idea to work on, which means it’s time to choose that specific idea. Your task is a lot easier if you followed the exercise above and have let go of ideas and projects that aren’t as important. A bunch of little, less important ideas can add up to overwhelm in the same way that a bunch of little, less important requests can.

Before we get to the questions that will help you pick the one idea to work on, know that “not now” isn’t the same thing as “no.” By picking one idea, you’ll be saying “not now” to others—this is displacement in effect—and it can often feel like “not now” means the same thing as “no.” Intentionally not working on an idea typically feels more uncomfortable than unintentionally not working on it, but deciding not to work on an idea frees up that energy and focus to intentionally finish and work on another. Better to use the five keys (especially courage and discipline) to intentionally finish one idea than to not use them and unintentionally not finish a bunch.

You may also avoid choosing because you’re afraid you’ll pick the wrong thing. Remember, if you finish the idea sooner, you can move on to something else sooner without the baggage and debt of the current idea and will thus finish the next idea faster.


Take the short list from the section above and use the following five questions to pick the project that matters most.


1. Imagine that you’re celebrating with a friend or loved one the most important thing you’ve done over the last year. If you could only pick one of the items on the list, which would it be?


2. Which of the items on the list causes the most gut-level anguish when you consider cutting it from the list completely? If you’re not sure of what I mean by gut-level anguish, imagine your most cherished object being destroyed in a fire. Which item, if removed, causes that feeling the most?


3. Which of the items on the list are you most likely to wake up for two hours earlier, stay up for two hours later, or steal time elsewhere to create two hours to do?


4. Which of the items on the list, if finished, will matter the most in five years, in terms of having done it or how it sets up your future self for thriving?


5. of the items on the list is worth claiming one of your remaining “significant project” slots? Recall from the section on displacement that you have a number of significant project slots equal to (85 minus your age) divided by 5 (rounded down).


Ideally one idea will emerge as the clear winner, but in the real world, one or three might be relatively tied depending on which of the questions gets the most weight. In the case of this kind of tie, go with the idea that wins on question 3, not because question 3 is the most important one, all things considered, but because it’s better to get momentum on one idea that you’ll create time for than others that you won’t.


Once you’ve made the choice, do the following three steps:


1. Circle the idea you’ve chosen to work on.


2. Put a date on the top of the piece of paper you’ve been working from so you know when you made this choice.


3. Take a picture of the piece of paper so you have a digital record of it and put the physical piece of paper someplace where you’ll see it a few times a week. This could be on a corkboard or whiteboard, your refrigerator, or framed on your desk.


The three steps above will free up a significant amount of energy in the long run because (a) you won’t have to make the choice again; (b) if you lose your list, you have a backup; and (c) you’ll be reminded of the ideas you didn’t choose at the same time that they’ll get some background incubation while you’re finishing the one you did. The few minutes it will take to do the three steps above will give you weeks and months in the future.

It’s time to start finishing your idea. If “finishing an idea” sounds funny, you’re ahead of the game, for we don’t do ideas, we do projects. Converting your idea into a doable project that you’ll finish is what we’re getting into next.


Chapter 3 Takeaways


• The more something matters to you, the more you’ll thrash, precisely because its success or failure is deeply important to you.


• Not doing your best work leads to creative constipation—at a certain point, you’re too toxic to take new ideas in because you’re not getting them out.


• We are but the latest in the line of gritty problem-solvers—we were made to slay dragons.


• The gift of failure is that it reveals what matters to you, shows you when you’re out of alignment, and reveals a growth edge.


• Displacement—the fact that doing something now excludes doing anything else—can help you focus on what matters, but only after you accept the limitations of time and energy.


• You have to let go of projects and ideas that aren’t allowing you to thrive so you can trade up to the projects that do.


• “Not now” isn’t the same thing as “no.”




(1) Wired magazine founder Kevin Kelly attributed this to Stewart Brand in Tim Ferriss’s Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers (New York: Houghton Mifflin Harcourt, 2016).


(2) See Chris Anderson, Free: The Past and Future of a Radical Price (New York: Hyperion, 2009).



About the author

Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the forthcoming book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast. view profile

Published on September 24, 2019

Published by Sounds True

70000 words

Genre: Business & economics

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