189: Deadlines are Magic

189: Deadlines are Magic


Don't sleep on the power of attaching a timeline to your goals, big and small

This issue of Cultivating Resilience is brought to you by the world greatest social writing cohort and a new group coaching program for outliers in transition run by yours truly. More at the end.

The streets were heavily snowed and iced over when I first arrived in NYC just over 10 year ago. But in recent years, snow has gotten more and more scarce, and barely there at all last winter.

I say all that to explain that I'm trying to stay grateful for the snow that has arrived in the last few days. It's thick, fluffy, and actually sticking to the ground. Anyways, onto today's newsletter

We've all experienced the power of deadlines.

"Our Uber will be here in 5 minutes" is a deadline, as is, "We have review the new budget with the board on Friday", as is "You have 3 weeks to make your quota for the quarter" as is "America will put a man on the moon by the end of decade".

Each of these statements describes a time in the near future (relative to the task at hand) where something is expected to occur, and where real consequences are at stake.

I believe there's a magical power in deadlines.

Our brains need these kinds of deadlines, especially if you have ADHD like me or many of the clients I work with. In particular, deadlines help us with the two important things we have to do:

  • Getting work done
  • Making a decision

Deadlines are a kind of extra motivational juice. They provide clarity, visibility, and urgency to a task or decision and help bring it to life.

Uncertainty and the Quarter-Life Crisis

Deadlines and their cousin, timelines, provide a sense of clarity in a chaotic world.

I'd argue one of the reasons many twenty-somethings feel lost is that they go from a world that's full of deadlines: homework, problem sets, papers, quizzes, major requirements, rush week, grad school applications, are all activities and events with explicit deadlines.

Then you enter the workforce and slowly the deadlines disappear. You join a company along with a bunch of other people who might be your age, maybe some are older. They are on different timelines, have different goals, and start diverging in their activities and life choices.

You won't get promoted at the same schedule, nor will someone tap you on the shoulder and tell you its time to change roles, move cities, or stop buying IKEA furniture.

God forbid you quit, get laid off, or are fired and find yourself unemployed. There's no set time for long it will take to get a new job, how much time you have to apply to a job before it closes, etc.

This level of uncertainty can be incredibly disorienting and anxiety-inducing.

Deadlines and Startups

Uncertainty is also something strikes startup founders. There's no set amount of time for raising your next round of funding. No deadline that says if you don't reach product market fit by a certain date you're dead. And no length of time that guarantees you'll have made a key hire into your business.

There's a reason that startup accelerators emerged to create structure from an inherently unstructured process. By setting a deadline—10 weeks of intense work followed by a golden opportunity to pitch startup founders—Y Combinator, Techstars, and other programs help emerging entrepreneurs do far more than they otherwise could imagine.

There's even the concept of the Post Demo Day Slump, an phenomenon that strikes founders who find themselves oddly less motivated and focused without a deadline to push towards.

Setting a Deadline for a Pivot

A number of my clients have considered changing the direction of their product, and what we often get to is, you guessed it, setting a deadline.

In my book The Path to Pivot, I call this a "pivot pilot", meaning a structured time frame for exploration before making a final decision. So before you go all in on your pivot, you pilot the pivot. You put your main business on maintenance mode while you really push on the new direction for 2, 4, or even 6 weeks.

This approach does a couple of things

  • It helps people get comfortable with the idea of the change, because it's not like a full commitment, it's a test commitment.
  • Whether it's you, your co-founders, your team members, your investors, this deadline period is sort of a liminal space between the full change, and it helps us all psychologically get more used to it, and get more information as well before making a final choice.
  • It makes the final decision feel more binding and real, because there was a extended period of time before where the decision was being carefully weighed.

Deadlines Beyond Business

You can apply the magic of deadlines to just about anything. Trying out a new habit or routine? Set a deadline to reevaluate in a month.

Yes the ever popular 30 day challenge is a kind of deadline. It says that you will commit to a certain behavior or way of being for 30 days before getting a "break".

  • Flossing
  • Journaling
  • Cold showers
  • Taking a photo
  • Learning to code
  • Posting on social
  • Walking 10k steps

Knowing you can take a break in certain amount of time is key.

In middle school I would go running to improve my cardio with an older gymnast my mother coached named Juliana. I hated running and dreaded these training sessions, but worst of all, Juliana would never tell me how long we were running for.

There was no deadline, which made the runs drag on, and I'm sure I complained something awful.

Compare that to the workouts of Crossfit or Apple Fitness or Peloton. They all have built in deadlines. In Crossfit, almost every workout follows one of 3 deadline styles:

  • AMRAP- As Many Rounds as Possible (within a certain timeframe)
  • EMOM- Every Minute on the Minute (you start again at the top of the minute)
  • FT - For Time (you do the assigned workout as quickly as possible)

How to Make Your Deadlines APAP (As Powerful As Possible)

At this point you've either bought into the power of the deadline or you've stopped reading. So I'll leave you with some important strategies that make the deadline

  • Keep the Deadline Short: You need a deadline that's not too far away. Research shows we accelerate our activities once cross half to the deadline, and its easier to get off track if you have an extended "slack off" period
  • Set More Deadlines: If you've got a big goal, set multiple deadlines. You can think of them as milestones towards your final objective.
  • Commit to the Deadline: Once set, resist the urge to adjust the goal or make the decision prematurely. Allow the process to unfold within the designated timeframe.
  • Invite Accountability: Share your goals and deadlines with others to create a sense of commitment and receive support. Invite people to a 15 mins calendar event to announce the final result of a decision or where you got to
  • Visualize the Timeline: Use calendars, progress bars, or daily check-ins to keep the deadline in sight and maintain focus. The more you can keep the deadline in mind, the more effective it will be.

Lastly, don't beat yourself up over not hitting the deadline. By all means, try your absolute best to hit it, but realize that even if you fell short, you probably got more done than you otherwise would.

And if nothing else, you calibrated your own brain for the next deadline you're going to set, so you'll be more accurate next time.

So that's what I got this week, the magic of deadlines. I hope this is helpful, and I'll see you next week.


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How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.