Last week I crossed the six month mark being a full time entrepreneur, and there’s no going back. I’ve been committed since the beginning, and the last six months have only strengthened my resolve.
I’ve quite possibly reached the point of being unemployable 🤣
It’s way too fun being in charge of myself. I have so much freedom and breadth to explore. Relatedly, this quote came up in my Readwise review, from the Founders podcast about Haruki Murakami:
Go for freedom. Freedom allows you to control what you work on. If you control what you work on, then you can work on what you love. If you love it, you’ll do it for a long time. And if you do it for a long time, you’ll get really good at it and money will come as a result.
That’s the path I’m following! I have the freedom to work on what I love. I continue to refine what I love by experimenting with a lot of things, and the money is coming.
Last month was my biggest revenue month of the year. I’ve proven to myself that I can make money doing a variety of different things. Each win makes the next one slightly easier.
My biggest challenge? Business development / customer acquisition. All of my customers became customers because they either know me, or came to know me through an introduction. I’m working on how to scale that.
A smaller challenge is the sheer number of projects I’m working on, some of which are not paid. For example, I’m working on putting on a one-day conference here in Austin in November. I’m also working with people on building a non-profit angel investing group. Those non-paid projects either pull time away from paid work and business development, or, I don’t put as much effort into them, which detracts from my reputation.
Since all of this is fun and I’m learning, I want to do it all. But I can’t do every project under the sun. I can’t help every customer. I can’t start all the businesses. 😁
I may build a physical Work In Progress (WIP) board, with a fixed number of spots - including only so many unpaid projects - just to remind myself of my own capacity! I’m only allowed to say yes to a new project if I complete an old project, or new capacity comes online.
What’s nice is that these are fun challenges to have! So, I’m going to keep working on them. 😁
What challenges are you working on? Are they fun, in addition to being hard?
Kevin
A Quote
“
If we do not give ourselves permission to dream, how do we give ourselves permission to thrive? So give yourself the allowance to think about that thing that feels too big and too far to touch.
— Luvvie Ajayi Jones in "Professional Troublemaker"
This is a new game by Tim Ferriss and Elan Lee (of Exploding Kittens fame). You play with cards, but this is a very physical and cognitive game. We’ve had several laugh out loud moments playing together as a family. At only $10 (or $13 at Amazon), it’s a really inexpensive addition to the game cabinet.
I’m gaga over ESPN’s new app; not because of anything special they’ve done, but the fact that it’s been unbundled from cable, which I haven’t had for 20 years. I signed up last week and it immediately brought me back to college, watching GameDay on Saturday before college football. Last Saturday I watched three games at the same time, which surprised my family - who is this new sports-watching person?!
If you want an easy-going houseplant, this is the one for you. It’s been a champ for me, no matter how I treat it. Everything else is so finicky, but this has been solid, and has been rewarded with a primo spot on my work desk.
(please enjoy this 6️⃣ minute read)
Deep Dive on What Needs to be True
A leader is someone who leads people to a future that doesn’t exist yet. To get there, a leader will need to solve many problems. A leader will have to imagine what is possible, even if it’s not true today.
And one of the best questions to aid a leader in that process is: “What needs to be true?”
If you’re looking for a good question to build momentum in your business, you’ve come to the right place.
Ignore whether it’s possible
It’s quite easy to poo poo new ideas. “That’ll never happen because of [x].” 💩
“Whether you think you can, or you think you can’t—you’re right.” - Henry Ford
If you don’t think something’s possible you won’t try, which makes it a self-fulfilling prophesy!
The “What needs to be true” question is great because it ignores whether something is possible or not.
You’re just asking what would have to be true for something to work. It breaks you out of a self-defeating mindset.
Therein lies the power. You’re momentarily ignoring feasibility, and just asking, for the future you’re imagining, what would need to be true for it to exist.
Just by exploring what needs to be true, a few things start to happen. a) You’ll get more creative ideas. b) By saying things out loud, you’re making it feel more real.
It’s a creative powerhouse question. It’s a momentum builder.
It’s not as hard as you thought
By listing out what needs to be true, you often find that the list isn’t as hard as you imagined before you started.
This is one of the reasons that journaling through anxiety is so powerful. You get a tangled mess of thoughts that feel overwhelming out of your head and onto a piece of paper. When you stare at your thoughts on a piece of paper, they lose their power. They become abstract things you can deal with.
The same thing is true for your leadership.
The list of what needs to be true becomes the plan of attack. And seeing it on paper makes it much easier to develop a plan than when you were trying to keep everything in your head.
Groceries, and how this question can be nested
As a simple example to illustrate how this works, think about your weekly grocery trip. What needs to be true to buy groceries? - You need to know what to buy - You’ll need a place to buy them - You’ll need transportation to the store and back - You’ll need a way carry the groceries - You need money!
None of these break the laws of physics, so you can build a plan of attack. - You’ll need a list. - Look for the closest store - Drive, or get a ride - Bring bags - And your wallet
Simple. Most of us do this without even thinking consciously about it.
Chillin' after a successful grocery trip.
And then someone like Instacart took the same concept, and asked, what needs to be true for customers to buy groceries without going to the store? - You’ll need a database of food. - You’ll need real-time availability. - You’ll need people to shop for groceries, check them out, and drive them to each house. - You’ll need a way to accept payment. - And likely a hundred other things.
This thought process makes it possible to start solving each of these problems. You might have already noticed that “What needs to be true” can be applied at each layer.
What needs to be true to get a database of food? What needs to be true to get real-time availability? What needs to be true to have a full capacity of trained staff? What needs to be true to accept payment?
Think about how the people at SpaceX needed to use a question like this. Or how the current crop of robotics companies are thinking about this.
This question breaks down a complex and uncertain future and starts to make it tangible and real - so you can make progress on getting there.
Please, use this in your long-range planning work!
There’s a nuance with the “What needs to be true” question: Even though part of its power lies in letting you ignore what’s possible, the act of answering this also reminds you what must be possible for you to succeed.
This is often a huge failure in long-range planning exercises, often accompanied by OKRs or another goal-setting methodology.
Leaders treat this exercise as a wish list. They’ll put down all the things they want to be true, and ignore what needs to happen to make it true.
After the wish list gets published, the teams in charge of executing that plan begin the work of making it feasible, only to find out that there are conflicts, insufficient resources, or myriad other issues that immediately insert risk into the plan.
Don’t be the type of leader who is disconnected from reality.
Planning work isn't the time to put yourself in the clouds.
Incorporate this question into your planning cycles. One of the four things that go into making a good KR is that they are “aggressive, yet realistic.” You can’t ignore the realistic part.
The application of this question in strategy work also shows up in the excellent book, “What a Unicorn Knows” by Matthew E. May and Pablo Dominguez:
1. What must be true about the openness, structure, and dynamics of our chosen spaces?
2. What must be true about what our company, channels, and customers value?
3. What must be true about our critical capabilities and relative costs?
4. What must be true about how our competitors might react to our strategy?
Answering these questions should result in multiple assumptions and preconditions for success. The most uncertain of these—those that are most worrisome—may in fact be giant leaps of faith, critical risks and potential obstacles that must be tested and validated to the level of collective confidence that produces a belief that the What Must Be True is actually true.
Be humble and curious with your team
Imagine your team comes to you with a new idea. They’ve probably been working on it for weeks. They’re excited, they need your approval, and they can’t wait to walk you through it.
You, on the other hand, have never seen this work before. You’ve been in back to back meetings all day. You’re tired and stressed.
Most leaders in this situation will be tempted to rely on their intuition when evaluating the team’s idea. Maybe your intuition tells you this is a bad idea and it’ll never work. But your intuition is unreliable in your stressed state.
Instead of the telling the team, “No, because…” and listing out what you think is wrong, ask them, “What needs to be true for this to work?”
Two things will happen; either the team will educate you on why this is amazing and is totally going to work, or they’ll realize they haven’t thought through all of the challenges and have some more work to do.
It’s win-win! If you were right anyway, all you lost is a few minutes of discussion. If you were wrong, you learned something and still reinforced a positive, psychologically safe interaction with the team.
This also works on your behavior and identity
So far all of today’s examples and discussions relate to practical applications at work. Solving problems and getting things done. But this can also apply to your mental world as well.
Let’s say you’ve gotten feedback that you need more “leadership presence” - a nebulous concept, but one that appears on many people’s development plans. Ask yourself, “What needs to be true for me to have more leadership presence?”
You might generate a list that looks like this: - My points have structure (3 beats) and an example. - I name the decision, owner, and next step out loud. - My voice projects, I speak slower than my default, with clean pauses. - I open meetings by naming purpose, stakes, and decision rights. - I close with a crisp recap and commitment check.
So much presence, she glows.
Just like before, you can turn that list into actions and examples: - Example opener: “We’re here to decide X. The options are A/B/C. I lean B. Let’s surface objections for 7 minutes before I make a decision.” - Example closer: “We decided on B. The DRI is Priya. The go-live must be by Oct 1. My action is to unblock legal by Tuesday.” - Swap language: “I think maybe…” becomes “I recommend… because…” - I set my posture with intention before meetings start.
Use this for any type of behavior or identity issue you want to develop. Just like with our practical examples, ignore whether you feel like you can do any of those things at first, just list out what would need to be true. Once you get the list, you’ll see that it’s not as hard as it seems - it just takes practice and consistency.
Call to Action
The question “What needs to be true” has many helpful use cases. It can open up a world of possibility. It can develop a plan of attack. It can create positive interactions with your team.
You can use it for long-range planning and OKRs. You can use it for small projects. You can even use it to modify your behavior and identity!
Where are you feeling stuck? What feels impossible?
Break out this question and brainstorm for a little bit - and watch yourself get unblocked.
