Dream in Years, Plan in Months, Ship in Days

This guideline pops up often inside Automattic via folks like Matt, or me, on internal memos when discussing how best to balance product planning, strategy, and execution. With a bias toward action, we aim to learn more quickly by launching directly to users and customers.

Source: I first saw this message in 2015 via a tweet by Luke Wroblewski.

Luke later shared a poster version on Twitter in 2016, which I purchased for my office Zoom background (buy on Startup Vitamins).

DJ Patil, US Chief Data Scientist during the Obama administration tweeted an expanded version in 2017:

Here’s the full text from DJ’s hand-written note on White House stationery.

Dream in years
Plan in months
Evaluate in weeks
Ship daily

Prototype for 1x
Build for 10x
Engineer for 100x

What’s required to cut the timeline in half?
What needs to be done to double the impact?

DJ Patil

I love this philosophy for product strategy and execution because it puts the right balance on each activity.

Dreams take time and effort to accomplish, and a clear product vision means looking ahead enough to inspire and motivate people to join the mission.

When we don’t know an accurate launch date at the beginning, monthly plans split the work into smaller projects and tasks that’ll bring improvements out to the public quicker. This means we learn faster, measure the immediate impact of a launch, and track usage as close as possible to real-time.

Speed matters in marketing, business, and product development. Sometimes we aren’t confident the current change is the right one, yet shipping before we’re fully confident leads to a smarter set of next changes — informed by the people using the product.

Ship daily, measure weekly, and plan in months to find out what works sooner than later.

🚀

Manage During a Crisis: Deliberate Calm + Bounded Optimism

Enjoyed this timely and practical organizational leadership guide from McKinsey.

Key elements include priorities, roles, time, and energy.

Deliberate calm: How to steer into the storm.
Bounded optimism: How to mix confidence and hope with realism

As human beings, we can practice integrative awareness before, in, and after the moment.

Screenshot from the McKinsey study on personal operating models.

Six steps:

  1. Adapt your personal operating model.
  2. Set your intention.
  3. Regulate your reactions.
  4. Practice reflection.
  5. Reframe your perspective.
  6. Manage your energy.

Leadership in a crisis like this is an enormous responsibility, yet it can also be seen as a great privilege. Integrative awareness keeps leaders centered in the storm, giving them the focus they need to take care of themselves and the people and organizations they lead.

Lead with purpose!

Deal With Unresolved Grief By Looking Outward

Grief is inevitable. Unresolved grief doesn’t have to be. To overcome grief, leaders must become consciously aware of the problem; accept the pain of the loss; and take actions to first let go of the past, and then to find new meaning from the experience.

Via The hidden perils of unresolved grief (McKinsey)

The outward shift described here resonates with me as an action I can take every day. Under my control to break the inner gaze — the running loop of emotions in my mind — with frequent pauses to stop the cycle. Like an athlete would: train, play, rest, and recuperate to replace depleted energy. Same thing, but mentally.

Opening up emotionally allows those who have suffered from unresolved grief to restart the process of bonding with other people. As their focus shifts outward, their internal dialogue shifts from defensive to positive. This brings calm, clarity, gratitude, and even playfulness.

Thought-provoking prompt from McKinsey for anyone feeling overwhelmed, grief-sick, and exhausted: Hidden perils of unresolved grief. Food for thought for leaders and our teammates alike. “Grief can be a creative force that turns loss into inspiration.”

Kathleen Eisenhardt on Simple Rules To Unblock and Make Faster Decisions

When analyzing my work with teams, projects, and my own contributions I often try to find the bottleneck in the system. What’s blocked? How could we move faster? What’s are the important decisions?

Kathleen Eisenhardt is a professor at Stanford University who dives deep into these questions, and more. Below are two examples that share insights from her work around complex systems, decision making, and how simple rules can make all the difference.


Kathleen Eisenhardt: What Are Simple Rules? — We’re more likely to remember and act on 2-5 simple rules.


Kathleen Eisenhardt: Effective People Think Simply — You can make decisions faster when the rules are simple.

Start from both ends — open versus closed, and structured/complex versus chaotic.

What are the likely scenarios?

  • Product development teams that are highly complex might launch the wrong product very efficiently.
  • Product development teams that are highly chaotic — and anything goes — have a great time launching nothing.

Questions to ask:

  1. What are we trying to achieve?
  2. What’s the bottleneck in the process? What keeps us from achieving our goals?
  3. What are the rules? For example, understand your own data while also bringing in outside experts.

You can make decisions faster when the rules are simple.

“Stopping” rules are the hardest to learn. People are good at starting! Bad at stopping.

One of the biggest mistakes business people make is staying in something too long. A stopping rule helps you get out of that.

Kathleen Eisenhardt

Involve people around you to determine the rules — they shouldn’t just be from the top.

I hope you learn as much as I did from Kathleen Eisenhardt’s work.

SOUL-mate Decision Framework

I love this “SOUL-mate decision-making framework” shared by Aman Bhutani, CEO of GoDaddy. How do you know if a current, or new, role fits well?

Something you want to do.
Opportunity to help people more than yourself.
YoU should bring something special and unique to the role.
Learning is key, there has to be something you’re learning in the role.

Hat tip: Matt.


The S is for Something you are hungry for (not just interested or passionate about – truly hungry for). This will make sure you wake up every morning ready to succeed in the new role.

The O reminds you that there should be opportunity for everyone and not just you. Successful people do a lot of things right, and luck plays its part, but they also ride waves.

The U means that YOU must bring something special to the table. There must be a reason you are a match – you should have a competitive advantage over others.

Finally, L is for learning. If you are not going to learn anything, don’t take it. Remember that this often comes from the people just as much as the role itself.

Aman Bhutani on Twitter

Leaders Shorten the Distance

Our job as leaders is to close the gap between the inconceivable to some but inevitable to us.

Paraphrased from Nancy Pelosi’s 2020 commencement address as Smith College (emphasis mine).

During this crisis and in the days, years, and weeks that will follow, the world needs your leadership too,” Pelosi said to the graduates. “Our goal as leaders is to shorten the distance between the inconceivable to some, but inevitable to us … Because Smithies are relentless and persistent, I’m confident in your ability to do so,” she continued.

Boston.com

From Panic to Bewilderment

“The first step is to tone down the prophecies of doom, and switch from panic mode to bewilderment. Panic is a form of hubris. It comes from the smug feeling that I know exactly where the world is heading — down. Bewilderment is more humble, and therefore more clear-sighted. If you feel like running down the street crying ‘The apocalypse is upon us!’, try telling yourself ‘No, it’s not that. Truth is, I just don’t understand what’s going on in the world.”

Yuval Noah Harari in 21 Lessons for the 21st Century.
Bewilderment is more humble

Via Book Freak Issue #51 by Mark Frauenfelder, a newsletter with “short pieces of advice from books.” Hat tip, Matt.

Beginnings

It is always hard to believe that the courageous step is so close to us, that it is closer than we ever could imagine, that in fact, we already know what it is, and that the step is simpler, more radical than we had thought: which is why we so often prefer the story to be more elaborate, our identities clouded in fear, the horizon safely in the distance, the essay longer than it needs to be and the answer safely in the realm of impossibility.

This very simple step is all that is needed for the new responsibilities ahead.

From Consolations by David Whyte.

Review: Everything is Figureoutable

Everything is Figureoutable

Everything is Figureoutable by Marie Forleo.

My Goodreads rating: 4 of 5 stars.

This is a powerful, pragmatic, and motivational reference that I’ll revisit again each year.

The basic premise throughout is that any problem, dream, goal, or task are figureoutable. Meaning that if I break it down into achievable steps, face my fears about starting it, and truly want to say “yes” to it — and then take full responsibility for failing and learning from the experience — I can and will “win” because I learn and grow.

All you need is one core meta belief, a master key that unlocks every imaginable door in the castle of your consciousness. It’s like throwing a switch that instantly illuminates a field of infinite potential. If you haven’t yet guessed, the whole purpose of this book is to inspire you to adopt the supremely powerful belief that everything is figureoutable!

Marie Forleo

The book is full of coaching tips, motivational stories, and testimonials from people who follow Marie’s teachings on MarieTV and her B-School course for entrepreneurs.

Read on Kindle, free from my local library.

View all my book reviews, and see my books on Goodreads.

An Advice Process Paves the Way for Clear Decisions

In Brave New Work Aaron Dignan describes a wonderfully clear way to use an “advice process” to make better decisions.

Watch a short video on YouTube where author Aaron Dignan illustrates the advice process (at minute 4:45).

Start with consent by asking for agreement. Get buy-in and move things forward. This not consensus or everyone is 100% happy with it, instead it means it is safe to try.

Use an advice process. Whenever you’re about to make a decision that’s irreversible or could damage things, go seek advice from those who’ve done it before. And, seek advice from those affected by it.

This replaces the waiting and expectation for a leader to do something—top-down decision making—with your own judgement and responsibility.