This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.

Peter Thiel studied philosophy as an undergraduate.

Peter Thiel has $7.36 billion.

Peter is a world-ranked chess player, has a legal degree, and has written profitable novels.

In 1999, he co-founded PayPal with Max Levchin, which merged with X.com.

Peter Thiel made $55 million after selling the company to eBay for $1.5 billion in 2002.

You may be wondering…

How did Peter turn $55 million into his now multi-billion dollar net worth?

One amazing investment?

Facebook.

Thiel was Facebook's first external investor. He bought 10% of the company for $500,000 in 2004.

This investment returned 159% annually, 200x in 8 years.

By 2012, Thiel sold almost all his Facebook shares, becoming a billionaire.

What was the investment thesis of Peter?

This investment appeared ridiculous. Facebook was an innovative startup.

Thiel's $500,000 contribution transformed Facebook.

Harvard students have access to Facebook's 8 features and 1 photo per profile.

How did Peter determine that this would be a wise investment, then?

Facebook is a mimetic desire machine.

Social media's popularity is odd. Why peek at strangers' images on a computer?

Peter Thiel studied under French thinker Rene Girard at Stanford.

Mimetic Desire explains social media's success.

Mimetic Desire is the idea that humans desire things simply because other people do.

If nobody wanted it, would you?

Would you desire a family, a luxury car, or expensive clothes if no one else did? Girard says no.

People we admire affect our aspirations because we're social animals. Every person has a role model.

Our nonreligious culture implies role models are increasingly other humans, not God.

The idea explains why social media influencers are so powerful.

Why would Andrew Tate or Kim Kardashian matter if people weren't mimetic?

Humanity is fundamentally motivated by social comparison.

Facebook takes advantage of this need for social comparison, and puts it on a global scale.

It aggregates photographs and updates from millions of individuals.

Facebook mobile allows 24/7 social comparison.

Thiel studied mimetic desire with Girard and realized Facebook exploits the urge for social comparison to gain money.

Social media is more significant and influential than ever, despite Facebook's decline.

Thiel and Girard show that applied philosophy (particularly in business) can be immensely profitable.

Managers spend much time in 1:1s. Most team members meet with supervisors regularly. 1:1s can help create relationships and tackle tough topics. Few appreciate the 1:1 format's potential. Most of the time, that potential is spent on small talk, surface-level updates, and ranting (Ugh, the marketing team isn’t stepping up the way I want them to).

What if you used that time to have deeper conversations and important insights? What if change was easy?

This post introduces a new 1:1 format to help you dive deeper, faster, and develop genuine relationships without losing impact.

A 1:1 is a chat, you would assume. Why use structure to talk to a coworker? Go! I know how to talk to people. I can write. I've always written. Also, This article was edited by Zoe.

Before you discard something, ask yourself if there's a good reason not to try anything new. Is the 1:1 only a talk, or do you want extra benefits? Try the steps below to discover more.

I. Reflection (5 minutes)

Context-free, broad comments waste time and are useless. Instead, give team members 5 minutes to write these 3 prompts.

1. What's effective?

2. What is decent but could be improved?

3. What is broken or missing?

Why these? They encourage people to be honest about all their experiences. Answering these questions helps people realize something isn't working. These prompts let people consider what's working.

Why take notes? Because you get more in less time. Will you feel awkward sitting quietly while your coworker writes? Probably. Persevere. Multi-task. Take a break from your afternoon meeting marathon. Any awkwardness will pay off.

What happens? After a few minutes of light conversation, create a template like the one given here and have team members fill in their replies. You can pre-share the template (with the caveat that this isn’t meant to take much prep time). Do this with your coworker: Answer the prompts. Everyone can benefit from pondering and obtaining guidance.

This step's output.

Part II: Talk (10-20 minutes)

Most individuals can explain what they see but not what's behind an answer. You don't like a meeting. Why not? Marketing partnership is difficult. What makes working with them difficult? I don't recommend slandering coworkers. Consider how your meetings, decisions, and priorities make work harder. The excellent stuff too. You want to know what's humming so you can reproduce the magic.

First, recognize some facts.

• Real power dynamics exist. To encourage individuals to be honest, you must provide a safe environment and extend clear invites. Even then, it may take a few 1:1s for someone to feel secure enough to go there in person. It is part of your responsibility to admit that it is normal.

• Curiosity and self-disclosure are crucial. Most leaders have received training to present themselves as the authorities. However, you will both benefit more from the dialogue if you can be open and honest about your personal experience, ask questions out of real curiosity, and acknowledge the pertinent sacrifices you're making as a leader.

• Honesty without bias is difficult and important. Due to concern for the feelings of others, people frequently hold back. Or if they do point anything out, they do so in a critical manner. The key is to be open and unapologetic about what you observe while not presuming that your viewpoint is correct and that of the other person is incorrect.

Let's go into some prompts (based on genuine conversations):

• “What do you notice across your answers?”

• “What about the way you/we/they do X, Y, or Z is working well?”

• “ Will you say more about item X in ‘What’s not working?’”

• “I’m surprised there isn’t anything about Z. Why is that?”

• “All of us tend to play some role in maintaining certain patterns. How might you/we be playing a role in this pattern persisting?”

• “How might the way we meet, make decisions, or collaborate play a role in what’s currently happening?”

Consider the preceding example. What about the Monday meeting isn't working? Why? or What about the way we work with marketing makes collaboration harder? Remember to share your honest observations!

Third section: observe patterns (10-15 minutes)

Leaders desire to empower their people but don't know how. We also have many preconceptions about what empowerment means to us and how it works. The next phase in this 1:1 format will assist you and your team member comprehend team power and empowerment. This understanding can help you support and shift your team member's behavior, especially where you disagree.

How to? After discussing the stated responses, ask each team member what they can control, influence, and not control. Mark their replies. You can do the same, adding colors where you disagree.

This step's output.

Next, consider the color constellation. Discuss these questions:

• Is one color much more prevalent than the other? Why, if so?

• Are the colors for the "what's working," "what's fine," and "what's not working" categories clearly distinct? Why, if so?

• Do you have any disagreements? If yes, specifically where does your viewpoint differ? What activities do you object to? (Remember, there is no right or wrong in this. Give explicit details and ask questions with curiosity.)

Example: Based on the colors, you can ask, Is the marketing meeting's quality beyond your control? Were our marketing partners consulted? Are there any parts of team decisions we can control? We can't control people, but have we explored another decision-making method? How can we collaborate and generate governance-related information to reduce work, even if the requirement for prep can't be eliminated?

Consider the top one or two topics for this conversation. No 1:1 can cover everything, and that's OK. Focus on the present.

Part IV: Determine the next step (5 minutes)

Last, examine what this conversation means for you and your team member. It's easy to think we know the next moves when we don't.

Like what? You and your teammate answer these questions.

1. What does this signify moving ahead for me? What can I do to change this? Make requests, for instance, and see how people respond before thinking they won't be responsive.

2. What demands do I have on other people or my partners? What should I do first? E.g. Make a suggestion to marketing that we hold a monthly retrospective so we can address problems and exchange input more frequently. Include it on the meeting's agenda for next Monday.

Close the 1:1 by sharing what you noticed about the chat. Observations? Learn anything?

Yourself, you, and the 1:1

As a leader, you either reinforce or disrupt habits. Try this template if you desire greater ownership, empowerment, or creativity. Consider how you affect surrounding dynamics. How can you expect others to try something new in high-stakes scenarios, like meetings with cross-functional partners or senior stakeholders, if you won't? How can you expect deep thought and relationship if you don't encourage it in 1:1s? What pattern could this new format disrupt or reinforce?

Fight reluctance. First attempts won't be ideal, and that's OK. You'll only learn by trying.

The holy grail of plain text task management is finally within reach

Plain text task management? Are you serious?? Dedicated task managers exist for a reason, you know. Sheesh.

—Oh, I know. Believe me, I know! But hear me out.

I've managed projects and tasks in plain text for more than four years. Since reorganizing my to-do list, plain text task management is within reach.

Data completely yours? One billion percent. Beef it up with coding? Be my guest.

Enter: The List

The answer? A list. That’s it!

Write down tasks. Obsidian, Notenik, Drafts, or iA Writer are good plain text note-taking apps.

List too long? Of course, it is! A large list tells you what to do. Feel the itch and friction. Then fix it.

• But I want to be able to distinguish between work and personal life! List two things.

• However, I need to know what should be completed first. Put those items at the top.

• However, some things keep coming up, and I need to be reminded of them! Put those in your calendar and make an alarm for them.

• But since individual X hasn't completed task Y, I can't proceed with this. Create a Waiting section on your list by dividing it.

• But I must know what I'm supposed to be doing right now! Read your list(s). Check your calendar. Think critically.

Before I begin a new one, I remind myself that "Listory Never Repeats."

There’s no such thing as too many lists if all are needed. There is such a thing as too many lists if you make them before they’re needed. Before they complain that their previous room was small or too crowded or needed a new light.

A list that feels too long has a voice; it’s telling you what to do next.

I use one Master List. It's a control panel that tells me what to focus on short-term. If something doesn't need semi-immediate attention, it goes on my Backlog list.

Todd Lewandowski's DWTS (Done, Waiting, Top 3, Soon) performance deserves praise. His DWTS to-do list structure has transformed my plain-text task management. I didn't realize it was upside down.

This is my take on it:

D = Done

Move finished items here. If they pile up, clear them out every week or month. I have a Done Archive folder.

W = Waiting

Things seething in the background, awaiting action. Stir them occasionally so they don't burn.

T = Top 3

Three priorities. Personal comes first, then work. There will always be a top 3 (no more than 5) in every category. Projects, not chores, usually.

S = Soon

This part is action-oriented. It's for anything you can accomplish to finish one of the Top 3. This collection includes thoughts and project lists. The sole requirement is that they should be short-term goals.

Some of you have probably concluded this isn't for you. Please read Todd's piece before throwing out the baby. Often. You shouldn't miss a newborn.

As much as Dancing With The Stars helps me recall this method, I may try switching their order. TSWD; Drilling Tunnel Seismic? Serenity After Task?

Master List Showcase

My Master List lives alone in its own file, but sometimes appears in other places.  It's included in my Weekly List template. Here's a (soon-to-be-updated) demo vault of my Obsidian planning setup to download for free.

Here's the code behind my weekly screenshot:

## [[Master List - 2022|✓]]  TO DO

![[Master List - 2022]]

FYI, I use the Minimal Theme in Obsidian, with a few tweaks.

You may note I'm utilizing a checkmark as a link. For me, that's easier than locating the proper spot to click on the embed.

Blue headings for Done and Waiting are links. Done links to the Done Archive page and Waiting to a general waiting page.

Read my full article here.

Decentralizing Web3's soul

Our tech must reflect our non-transactional connections. Web3 arose from a lack of social links. It must strengthen these linkages to get widespread adoption. Soulbound NFTs help.

This NFT creates digital proofs of our social ties. It embodies G. Simmel's idea of identity, in which individuality emerges from social groups, just as social groups evolve from people.

It's multipurpose. First, gather online our distinctive social features. Second, highlight and categorize social relationships between entities and people to create a spiderweb of networks.

1. 🌐 Reducing online manipulation: Only socially rich or respectable crypto wallets can participate in projects, ensuring that no one can create several wallets to influence decentralized project governance.

2. 🤝 Improving social links: Some sectors of society lack social context. Racism, sexism, and homophobia do that. Public wallets can help identify and connect distinct social groupings.

3. 👩‍❤️‍💋‍👨 Increasing pluralism: Soulbound tokens can ensure that socially connected wallets have less voting power online to increase pluralism. We can also overweight a minority of numerous voices.

4. 💰Making more informed decisions: Taking out an insurance policy requires a life review. Why not loans? Character isn't limited by income, and many people need a chance.

5. 🎶 Finding a community: Soulbound tokens are accessible to everyone. This means we can find people who are like us but also different. This is probably rare among your friends and family.

NFTs are dangerous, and I don't like them. Social credit score, privacy, lost wallet. We must stay informed and keep talking to innovators.

E. Glen Weyl, Puja Ohlhaver and Vitalik Buterin get all the credit for these ideas, having written the very accessible white paper “Decentralized Society: Finding Web3’s Soul”.