A System To Do Hard Things + a Bonus: The Freedom of Low Expectations

Apple | Spotify | Youtube

Sponsor: Byldd

Byldd is a startup studio offering MVP development services for startups. They’re focused on helping early-stage founders launch revenue generating businesses. Talk to Ayush ([email protected]) and tell him you came from the pod.

This Newsletter:

We’ll send it out with each episode now - hope it’s helpful. Share it with someone who’d like the pod!

Why This Episode Exists + Nerdy Stuff Not In The Pod 💡

Today’s episode is straightforward: Humans are meant to do hard things, we’re happier when we do hard things, and we’re capable of far more than we think. And, systems help.

Rather than dig deeper, I’m posting last Sunday’s newsletter to the Tacklebox members below. If you like the pod, you’ll enjoy it.

Reply “Sunday” to this email to get these regularly.

The Freedom of Low Expectations

There’s a minute and a half long video that a few people sent to me that I mostly like - here it is.

The CEO of Nvidia is talking about low expectations and resilience and suffering and, sure, he’s hamming it up a bit and he’s got the leather jacket and the dramatic pauses and he’s going for something (and it’s working).

But, the bit I want to zoom in on is the connection between talented, successful people and the expectations they have when they start a business.

If you’re getting this email, you’re in the top 5% or 1% or whatever of “achievers.” Which means you’ll naturally have high expectations because you’ve been successful in the past.

Unfortunately, high expectations are a disaster for entrepreneurship because of the fundamental way entrepreneurship works.

No matter how much domain experience you’ve got, the first set of things you do won’t work and they aren't supposed to. Because whatever you try first will be the same things everyone else with a similar idea would have tried first. We think we're all unique snowflakes but everyone's first three ideas are usually the same. And if one of those things could work, it would’ve. And it’d exist and the problem wouldn’t be there. Capitalism is efficient. There are no $20 bills on the sidewalk. 

The business you'll be successful with exists somewhere past where most people have already looked. Which means it takes time to get to. You’ve got to get all the crappy approaches out of the way first - the ones people have tried. 

And, while we try to speed this up as best we can at Tacklebox, it’s unlikely we’ll be able to skip the false starts. They’re where we learn what will work. You can’t jump the line.

Here’s what it looks like:

Basically, you need to try lots of things to be successful, and very few people try lots of things. 

Expectations are the culprit because they're the key (only) variable for happiness.

The happiness equation is simple: 

Happiness = Reality - Expectations

If your reality exceeds your expectations, you’re happy. It it doesn’t, you’re not.

Back to startups.

If you expect to be immediately successful with your startup, then you’ll be sad. Because the first 20 things you try won’t "work." And that's where the conflict shows up - trying things that don't work mean you're moving along that graph towards the successful business. This is a good thing. But, it makes lots of people sad.

And if you’re sad, you’re less likely to stick with your idea long enough for it to succeed.

Here’s a very scientific graph I made on happiness and startup expectations:

Low expectation people win, easily.

They’re happier fastest which means they’re able to stay in the game the longest. They've got alligator blood - they'll hang around until they get to a successful business.

The fastest way to be successful and happy is to lower your expectations. That doesn’t mean don’t work hard or don’t have high standards - just expect that what you do probably won’t work right away and know that the important part isn't that everything works immediately - it's that after it doesn't work, you hang around. Every thing that doesn't work is a step closer to the thing that does. 

Success is on the far right side of the graph - your job is to get there. Low expectations help. 

Pod References

• Byldd

• Tacklebox

Pod Timestamps:

00:24 Doing Things You Don’t Want To Do
02:45 Why the Eisenhower Box Doesn’t Work for Entrepreneurs
03:30 The Al Pacino Problem
04:45 Creating Content
08:00 Smooth Jazz
08:30 The Costanza Swap
10:15 One Out, One In
11:20 The Three Levers of Resilience
12:40 Scheduling
13:24 Committing
14:30 Dissecting
17:40 The Failure Case
21:15 Happiness

Transcript - Feel Free to Read it Like a Long-form Article:

Today, we’re going to help you do things you don’t want to do when you really don’t want to do them.

This is a core behavior of great entrepreneurs for two huge reasons.

First, none of us have done any of this before - 95% of the things you’ll be doing to start a startup are new. It’s like if someone said “hey, you’re going to host a barbecue next weekend for 350 people” and you said “there’s gotta be some mistake, I’m an accountant,” and they said “hey I’m just following orders” and walked away and then you had to find a venue and learn how to cook in bulk and rent a smoker and send out invitations and figure out tables and chairs and parking. Except in that scenario you’ve got plenty of information.

Your startup scenario has way more ambiguity.

Here’s an example.

Maybe you decide that a good way to test demand and build some awareness early on is to create a landing page and share it on a Slack channel where your customers hang out. Great.

This could be a good strategy, but you’ve never created a landing page before. So, you need to decide on wix or squarespace and figure out what to put in your header and whether you put a price on there and should you have a blog and do you make up testimonials and do you need to have a business incorporated to do this? Should you pretend the business is running or say you’ve got a waitlist?

Then, if you do get something up and on the Slack channel, now what? If you get one sign up… is that good? Bad? What if you get zero? Should you stop? Everything is new.

And that’s a problem, because new is uncomfortable and our core human drive is to avoid things that are uncomfortable. Literally, that impacts every decision you make. What option is least likely to cause discomfort.

So, entrepreneurs succeed when they do things their instincts are begging and pleading them not to do. This is a herculean task.

At it’s core, a startup is a collection of new, uncomfortable behaviors you’ll have to adopt and excel at, all while your inner voice is anxiously poking you and saying “hey, this seems risky… why don’t we just go watch a couple episodes of Monk instead?”

The second reason doing things when you don’t want to do them is a core successful entrepreneurial trait is because lots of things that could provide a ton of value but you don’t want to do won’t be urgent. So, you won’t do them.

Lots of entrepreneurs live by the Eisenhower Box as a productivity tool and decision maker. If you’re not familiar, it’s a simple four-box matrix with urgent on one axis and importance on the other. The point is to only do things that land in the two quadrants on the right - important and urgent, and important but not urgent.

The problem with this for entrepreneurs is they never end up getting to things that are important and not urgent because there are always plenty of things that are important and urgent, either relating to your startup or your day job or your personal life. And the non-urgent stuff is proactive, not reactive, which makes it more uncomfortable. Urgent is often easier and you can explain it away as your best use of time.

I call this the Al Pacino problem because most people only have time for the six inches in front of their face. I’m not going to do his voice from Any Given Sunday but just know I do have a great impression in my back pocket. Maybe later.

Anyway, this is useful to know when you’re choosing a customer to build for - your customer will only pay attention to stuff that’s immediate and urgent and solves a clear, obvious, painful problem - stuff six inches in front of their face, or what I, from this moment on, will call Al Pacino Problems. hooah,

But, it’s something we need to design for and overcome as we work on our startup, because to be different we need to spend time on the stuff that isnt right in front of our face, the important but not urgent stuff - this is usually the work that compounds - the stuff that doesn’t have much impact in six days but might fundamentally change our business in six months. The stuff other entrepreneurs avoid. The stuff that isn’t just right in front of us. The stuff with long feedback loops and no guarantees of success.

Most founders make decisions based on the floor - doing things that minimize the worst possible scenario. Startups work when founders aim to maximize the ceiling - what can happen in the best case scenario? But lots of those opportunities aren’t urgent, so they aren’t chased.

One of my favorite examples of important but not urgent - and wildly uncomfortable - tasks is creating content. And I’m not talking about content that you can outsource to chatgpt to improve your SEO - that’s all well and good and if you want to put up a token blog that no one reads for that reason, go for it.

I’m talking about content that could become a pillar for your business, or, maybe, the business itself. Content that can live in three different places of your all important funnel - content that helps people discover you, content that converts customers, and content that gets shared to help you grow organically.

Your first instinct is probably to lean away - you don’t want to make content because everyones got a blog or podcast, right?

No. Basically no one does. You probably don’t have a single friend with a consistent podcast or a blog. Your instincts are simply pushing you away from the idea because it’s extremely uncomfortable and it’s so easy to view the floor - the downside - and so hard to see the upside because it’s likely so far away. For the downside, you’ve probably never done it before so you don’t know what it takes, it’s a tangible thing people can judge you on and they might say it’s terrible, it might even be so bad people make fun of you, and it’ll take a long time to get any traction, anyway. These are all emotional and make believe.

But the upside could be massive and very real.

1. From a customer perspective, it’ll help you focus and think clearly and make choices. The key with content is picturing it as a tool to solve a specific, painful problem. The dam in the river that you’ll help your customer navigate to build trust. This framing forces you to think of a specific problem in a specific moment for a specific customer and to solve it persuasively in 700 words or a 4 minute video. It forces you to think up a compelling title that ideally describing the place you’ll get them to after the content is done solving their problem. It forces you to find your customer and drop this piece of content in their lap.

2. From a product perspective, a good piece of content acts as a lead magnet on your website to get emails, a trust builder in a cold email sequence, and something for your customers to share with each other so you grow organically. You might even get an industry publication to post it. This is a durable piece of work that could be used thousands of times.

3. From a business perspective, maybe the content becomes part of it. Maybe people pay for it. Maybe your voice resonates. In 2019 I certainly never thought a podcast would be the center of my business.

You can sub content for all sorts of things that’ll increase your luck surface area for your business, things that compound but are never urgent and rarely top of mind.

Today is about carving out space for them. To look past the six inches in front of your face. To do the things other entrepreneurs don’t do so you end up where most of them never get.

We’ll dig in on the system,

1. The Costanza Swap - how to decide what to work on

2. The three levers of resilience - your weekly execution plan

3. Building for Failure - what to do when the system breaks

After… a little smooth jazz.

The Costanza Swap

https://www.youtube.com/watch?v=CizwH_T7pjg

Most of your instincts around startups are going to be dead wrong.

That’s why I call this part of the system the Costanza Swap. There’s an episode of Seinfeld where George realizes that everything he’s done in life has been wrong, and he decides to do the complete opposite of every instinct he has. The scene ends with him walking up to a woman to try to pick her up with the line “My name is George. I'm unemployed and I live with my parents,” and it works.

This isn’t the worst way to think about how you should work on your startup idea. Whatever your instincts are pushing you away from is probably the thing you should lean into, because if it pushes you away it’ll push everyone else pursuing this idea away, too.

So, to stick with the content example, if you were immediately thrown off by content, maybe spend a few minutes reframing - if I were to be successful with content, what would it look like? If I had to write two posts a week, what would they be about? If I had to send one piece of content that solved a specific problem for my customers today, what would it be?

If you immediately push back on customer interviews, that’s probably what you should be spending time on. Your subconscious usually knows where you’re weak and protects you from uncovering it. The things with the most upside are the things other people don’t do, but our instincts will always push us towards the herd.

The second part of the Costanza Swap is the Swap part.

If you got excited about the content piece during the last minute and decided that you’re going to start a weekly newsletter, great. But, remember, we’re all goldfish. We’ve already grown to the size of our bowl, and you’ve got no time for anything new.

So, the first step of working on the uncomfortable stuff is deciding what you currently do that you’re going to stop. The Marie Kondo one out one in policy.

A newsletter might take you two hours a week, so, you have to find something you always do that takes two hours that you’ll stop. A good way to do this is to either look at your calendar from last week and pick the two least impactful hours of your week, or to track everything you do for the next week and figure out the tasks that drained your energy and weren’t a differentiator for your busiess. Figure out how to outsource the two hours or build a system to take them off your plate if they’re necessary, or drop them if they aren’t.

To summarize step 1:

First, you’re george costanza and your instincts are probably keeping you from a unique, differentiated business. Consider the opposite and try it out. Chicken salad, on rye, untoasted… and a cup of tea.

Second, you’re a goldfish and you’ve got no room for anything new. To work on something in a sustainable way, you’ve gotta drop something you always do first.

On to part two.

The three levers of resilience - your execution plan

The last thing you want to do is rely on willpower for the important but not urgent stuff, especially when it’s uncomfortable. We’ve got to create a system with inertia to make it easier to do this stuff than to not do it.

About a year ago a chronic back and head injury cleared up enough that I could start going to the gym again. After a few weeks of relying on my willpower to make that happen, I realized I needed a forcing function and got a trainer. Starting with once a week and building to my current schedule of 3x a week, I go down in my basement and hop on Zoom and do Turkish Getups and side planks and a bunch of other exercises contrived in the depths of hell and I feel great. About 65% of the time I’m absolutely dreading it - but ten minutes in I’m happy I’m there every time. And never once have I finished and regretted it. I’ve missed maybe 2 workouts the past year when I had covid and probably one here or there for a holiday, but overall it’s been life changing. The results have been fantastic and that anchor activity has a waterfall effect on the rest of my week.

The same sort of leverage can be applied for the uncomfortable stuff you don’t want to do. It’s got there parts - Scheduling, Committing, and Dissecting.

First, Scheduling. It’s exactly what it sounds like. You need a time dedicated to do the thing or it won’t happen. As a rule of thumb, anything that’ll take some willpower should be done first thing in the morning or it’ll get elbowed out by more quote urgent stuff later in the day.

There’s one rule for scheduling - if you schedule 6 to 645 on Wednesday morning to work on the uncomfortable thing, you have to sit down at your laptop at 6 and you can’t get up until 645 and during that time you don’t have to work on the thing you said you’d work on, but you can’t do anything else. No emails, no internet, not even meditation. You either sit quietly, staring at the wall, or work on the thing you said you’d work on. That’s it.

Second is committing. You need consequences for missing your scheduled time. For my workouts, I’ve gotta pay and my trainer gets pissed off because he’s in Hawaii and has to wake up early for our meetings. I’ll be out some cash and I’ll feel like a jerk. So, missing just isn’t an option.

There’s one rule for committing, too. The consequences need to hurt. Either it has to be public, or embarrassing, or expensive, or all three. Missing has to me more costly, in some way, than attending. This is crucial. The inertia needs to be naturally pulling you towards the thing rather than away.

There are all sorts of options here. A tool called WorkSitter lets you pay someone to sit on zoom with you while you work. Pulling together a group of three people working on startup ideas and picking out times to meet virtually or in-person to work and saying that if someone doesn’t show, they owe the other two $25 each. Hiring someone to edit your podcast each week requires you to get them a podcast each week. Whatever it is, it needs to be worse to skip and require no willpower.

Third, is dissecting. The goal here is to carry on the inertia created by sitting down to work. When I hop on zoom with my trainer, he tells me exactly what to do. I don’t have to think - I just do those horrific turkish getups while he yells at me to make sure my glutes are firing. If I hopped on Zoom and he said “so, what do you want to do today?” it’d be a disaster.

The work you’re doing is new, which is why it’s uncomfortable. The way to make something more comfortable is to be specific about what you have to get done and remove the mystery of “where do I start.” For example, when I schedule my time to plan the podcast, I break it up. FOr the first hour, Thursdays from 7-8am, my goal is to come up with 10 potential ideas for an episode and send them to a few of our engaged listeners to see what they think. That’s it. I’m not writing the full pod or even deciding on an idea. So, for the days leading up to that session, I’m pushing possible ideas as they come to make it even easier. In my next session, Mondays from 7-8am, I have to pick the idea I’ll pursue for the week and identify the big question I want to answer - the hurdle for the customer we’ll navigate. I then break that into a three part framework, with each part of the framework having an example.

Suddenly, I’ve got the skeleton of a pod and the rest is filling in the blanks and editing, something way less intimidating to me than a blank piece of paper.

The goal for all of this is to get rid of the blank piece of paper. To build frameworks you can fill in - to rush to the editing stage of whatever you’re doing.

Like the other two pillars, there’s one rule for dissecting - it has to be fun. You need to focus on the part of it you enjoy. This might sound odd, but it always works. Coming up with ten ideas is daunting, until I reframe the whole thing as an investiagtion and I’m sherlock holmes, thinking through all the startups I’m working with and the dams in their rivers, the things holding them up. When it becomes an investigation, I reach out to my founders often to get their side of the story so I can tell it. Maybe I ask them questions or ask to hop on a zoom quickly, because that’s what sherlock holmes might do and for whatever reason that’s fun for me. Even saying that it’s going to be fun for whatever reason makes the whole thing more approachable.

The point of the startup in the first place is to do something with your time you’ll enjoy - so make sure you’re focused on that.

To summarize step 2, you need to create the conditions to make the uncomfortable, longer feedback loop things easier to do than not to do.

This has three parts: scheduling, committing, and dissecting. Scheduling requires you to be there to work, committing penalizes you if you don’t, and dissecting makes it easy to get momentum during that working session.

And, turkish getups gets your glutes to fire so your butt will pop in a pair of jeans this winter. Or so I’m told.

The system works….

Until it doesn’t. And that’s the last, and most important, part of all of this.

The Failure Case

My dad took me fly fishing for the first time when I was 14. The goal was to have a father son bonding trip - neither of us had gone fly fishing before, but 8 hours on a boat together cruising down a river seemed pretty foolproof.

On our first day, our guide gave us a crash course on land before we hopped in the boat. The goal, he said, was to cast the line as close to the shore as possible. That’s where the fish were, under overhanging branches. this protected them from any eagles that might be cruising by, looking for lunch.

Great.

We started cruising down the river and I tried to cast my line right up against the bank. But, it’s hard. It’s windy and the boat is moving and my second or third cast landed in the bush and hooked a branch. We had to cut my line to get it back, and our guide had to spend ten minutes re-rigging my line.

A few minutes after that, I cast in the bushes again, and again we had to cut my line, pull the boat to shore, and re-rig it. Maybe 15 minutes later, it happened again.

I was mortified and decided that I was done trying to cast to the shore. I’d cast a safe distance away from the boat, making sure that I didn’t inconvenience this poor guy again - at least for an hour or so.

Within five minutes he realized what I was doing and stopped the boat.

“The fish are underneath the fucking bushes,” he said, “not in the gosh dang middle of the river. Now cast your line into the bushes.”

I looked at him, stunned.

“Go on, cast your line into the bushes.”

I did, and my line and hook got tangled in an overhanging tree.

He grabbed my line, pulled out his pocket knife, and cut it with a big smile.

“Now, let me get you set up with some new flies. Re-rigging your line is as much a part of fishing as catching fish is. You can’t expect to just perfectly cast your line against the bank and never overshoot it. Retying flies is part of it.”

I’ve worked with startups for about 10 years now and I think the biggest reason most founders end up stopping working on their idea is that they don’t realize that getting your line tangled in the bushes is part of it. That lots of times when you try something, it won’t work.

And that’s part of it.

It’s not an outlier so you can’t build your system to pretend it won’t happen.

You might do all the stuff we talked about and get a landing page out and get it in front of 250 of your best customers and ..no one clicks on it. This can be a momentum crusher. Or, you can think about it as tossing your line a few inches too far into the woods, and it’s time to regroup and try again. Because getting your line tangled in the bushes is part of it.

Something not working is an opportunity - it’s a feature, not a bug. Because every time you do something uncomfortable like run some new tests or run a new set of interviews with a different customer because the first one didn’t work pushes you further down the path on your own. It gets you further away from what anyone else will do. That’s a good thing. Each time you re-rig you’re giving yourself a better chance to catch a fish on the next cast.

I’ve got a friend who’s got a 4 year old and a 6 year old and every single time it rains he takes them outside to play. They have a system - a place for their boots and jackets and hat. They have an area of the house with towles and hanging racks. They have games they play in the rain - most involving sliding down muddy hills. Rains part of it, too, he says, and it’s not a bad thing. If you have a system for it.

Create a system to pick yourself up when you get knocked down. Don’t leave it to willpower.

Happiness.

I alluded to this a bit earlier, but the point of all this is happiness. You’re working on an idea because you think that’ll make you happier than doing something else. If that’s not the reason, I’d reevaluate.

But, people tend to misunderstand what’ll actually make them happy.

Happiness is about becoming who we want to be. And, if you’re listening to this podcast, that’s probably someone who does hard things. Who helps people solve hard problems. Who makes a dent.

You won’t get there with the comfortable stuff, and you won’t do the uncomfortable stuff consistently through sheer willpower. You need a system to to the hard things that will make you happy.

And doing the uncomfortable stuff over and over will make you the type of person who can do uncomfortable stuff when they don’t feel like it.

And those are the people who build things that matter.