A Thing That Always Works: The Five Minute List

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• The Seasons of your Business (and Life)

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

I absolutely love our Always Work and Never Work Lists, which means I absolutely love today’s episode. We dive deep on one of my favorite Methods from the Always Work List - the Five Minute List. It helps founders with jobs and time constraints stitch together disparate pockets of time into a real strategy.

Most of our founders have jobs and huge pulls on their time. We need those random, unpredictable 5, 10, 15 minute blocks of time to be hyper useful.

This episode teaches you how to make a list that’ll change your business.

Here’s some other nerdy stuff that didn’t make it in 🤓:

• The Zeigarnik Effect, which we use to talk about keeping your subconscious working, isn't just about memory - a study showed all sorts of applications, like waiters at a restaurant being able to perfectly recall unpaid orders but unable to remember completed ones. Your brain essentially puts a mental sticky note on unfinished tasks, which is why the 5-minute list works so well when tasks connect to the same theme. I think this is insanely cool and useful - open loops = your brain working in the background.

• In the Cal Newport book Deep Work we reference, he suggests that the cognitive "startup cost" of deep work is about 15 minutes. The 5-minute list works well because you're pre-loading that startup cost across multiple sessions - your brain keeps processing in the background between blocks. It lets you “re-use” that 15-minute onboard.

• I’ve been trying to figure out a way to make startups more like video games for years. I always think about “quest logs” and figuring out how to gamify the early stuff, like customer interviews. Nothing so far. Holler with ideas.

• I don’t touch on how to use these lists in the pod, but the two most common way for Tacklebox folk is the notes app and an index card in your back pocket.

And that’ll do it 🤓 

Have a great week!

Pod References

• XLR8 Dev

• Tacklebox Workshops

• The Midnight Library

• Sand and Stones Episode of Idea to Startup

• Deep Work

• Claude - my favorite current AI

• Idea to Startup Newsletter
   

00:33 Intro - The Always Work and Never Work Lists
05:22 The Five Minute List Part 1: Sand and Stones
08:29 Revenge of the Sand - a Founder Story
09:25 Pebbles
12:02 Your Subconscious
13:00 Four Steps to Build Your Five Minute List
17:16 The End - Coworking

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

Today, and over the next few weeks, we’re going to dive into the Always Work and Never Work lists and pull out a few of my favorite residents from each.

If you aren’t familiar with the Always Work and Never Work lists, these are lists I’ve been keeping for nearly a decade now at Tacklebox.

The boundaries for the always work and never work list are strict, and I bet you can guess them, but for the folks sitting in the back of the class - the stuff on the always work list always works, and the stuff on the never work list never does.

Are there exceptions?

No.

That’s the whole point of the list. This keeps them tight and tidy and wildly useful. Admission to either list is harder than admission into harvard, and we don’t let in legacies, so don’t even try, Lexington Pennyworth the fourth.

Anyway, the point of these lists is simple, but maybe counterintuitive. The always work and never work lists are about luck.

Using these firm, reliable methods give you the best chance at the least firm, seemingly unreliable part of building a business: Luck.

I like to think we’re all living one version of, say, 1,000 possible lives. It’s similar to that book the Midnight Library, if you’ve read it. And if you haven’t, you should.

The goal with the lists is to find the methods that’ll give you a chance at being successful in 999 of those 1,000 lives. And doing that will give you the best chance at what at Tacklebox we call the Luck Amplifier.

The equation for your startups success is the sum of your decisions times your luck amplifier. So, maximizing the quality of your base decisions creates more opportunities for the Luck Amplifier to kick in.

Most first time founders view luck as a thing they have no control over. But good founders recognize luck for what it is - a specific, measurable variable that gets tacked on to every action you take. Luck is a strategy, not a mystery. It’s math, not magic.

You can, and should, build, optimize and script luck. And we will, in an episode in a few weeks called How to Build Luck Amplifiers.

For today, though, we’ll focus on one core items off the Always Work list that’ll anchor that startup equation.

Last time we talked about the always work and never work lists someone reached out and asked if these methods eventually stopped working. They said that surely if everyone who listens to the pod started doing them, the unique value would disappear, right?

And yeah - the more mainstream a method gets, the less differentiation you’ll get from using it. Even the best methods have shelf lives - just look at the new brad pitt george clooney movie on netflix. It’s unwatchable, and I used to think I’d be happy watching those two hound dogs banter on screen about anything.

But, the stuff we’ll talk about today will work for you because it’s stuff that, even if 100 people know they should do it, 95 of them won’t. I know this because I’ve told hundreds of our entrepreneurs to do it, and they’re all great and still usually don’t.

So, you’ve just gotta be one of the five that do to see enormous value.

Enough rambling. Let’s get to the thing that always works.

And we’ll do it, after… A word from a new sponsor I’m very excited to be working with. Xlr8 dev, spelled xlr the number 8 dev dot com.

As you know, I'm picky about our pod's advertisers. That's why I'm excited to introduce XLR8 Dev, spelled X-L-R-8-dev.com. They solve a massive problem for our non-technical listeners: getting the first version of your product out, on time and on budget, before raising funds or hiring a CTO.

What separates XLR8 is that on-time and on-budget piece. This might sound like table stakes, but bloated scope and budget is nearly always the reason outsourced projects fail. First-time founders just aren’t equipped to manage a technical product.

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XLR8 can build apps or websites, they can salvage a partial product you had someone on Fiverr start, they're based entirely in the US, and, most importantly, they can do it all on time and on budget so that you can start generating customer feedback and revenue.

Contact Jaden at [email protected]. Mention "Idea to Startup" for our special listener deal on building your first product. Time to get something up and out.

Back to it.

A Thing That Always Works: The Five Minute List

Part 1: The Revenge of the Sand

In one of the first ever episodes of Idea to Startup, where I sound like a totally different person who’s somehow both more dramatic and less interesting, I talked about the sand and stones of startup work. I’ll put it in the show notes, it’s not as bad as I’m making it out to be.

The sand and stone metaphor is a common one. The idea is to visualize the time you work on your business as being contained in something that looks like an oversized mason jar. That jar holds all the time you spend on your startup. What you put in the jar are the two types of work most founders do early on - represented by sand and stones.

Stone work, or what Cal Newport calls Deep Work, requires longer, unbroken chunks of time. A three hour block to build out a high level customer acquisition plan for customer interviews, or five hours to synthesize those interviews and build a customer journey map for your customer’s current process - actions up top, emotions beneath. If you have 10 hours to work on your startup in a week, and you want to get three stones done, you need to find three three, hour-long blocks. Those stones will take up most of the jar. Stone work is often uncomfortable and usually proactive. It’s also unnatural if you haven’t worked on a startup before.

Sand work, on the other hand, is reactive. It doesn’t require big chunks of time and it tends to have short, superficial, but rewarding feedback loops. Answering emails, posting about your business on social media, setting up your LLC, creating a business plan, etc. It’s usually described as… comfortable stuff. The extra slice of pumpkin pie on the couch after Thanksgiving after you’ve already changed into your stretchy vuori sweatpants of entrepreneurship work.

The right approach is, obviously, to maximize the stone work and let the sand work fill in the cracks. But most entrepreneurs with jobs take the opposite approach. It’s hard to hold three uninterrupted hours and it’s harder to work on the deeper stuff. Plowing through emails and checking off surface level stuff feels more productive because that’s what productive is for non-entrepreneurs. So that’s what they do.

We’ve always tried to help our founders build systems around the stone work. Startups are about contrast - what you do that no one else does. Stone work, the uncomfortable stuff, is always the answer.

Anyway, you’re probably nodding along. Yes yes yes. Stone work. Deep work. You buy it. You struggle holding that time, but, you’ll really try harder to do it, Brian, you really will.

Maybe you even wrote yourself an email during that section that said HOLD SATURDAY MORNING FOR STONE WORK, DAMNIT!

And that’s great. Do it.

But, don’t beat yourself up yet. Because today’s method isn’t about stones or holding time for them.

It’s about the Revenge of the Sand.

I continue to work with a handful of the best founders from Tacklebox after they’ve outgrown the program. This is usually in an advisory capacity, so the types of meetings I have shift from hyper strategic one on ones to less frequent, broader “catch ups.” Usually over coffee or lunch.

A few years ago, I went to the bathroom during one of these lunches and came back to see the founder deep in something on her phone. What was she doing, I asked?

Five minute list, she replied.

She loved the sand and stone method, she explained, but she’d realized that it was often impractical. She had a job and a family, she’d only get, maybe, one three-hour block each week for deep work. So, she’d tried to figure out how to create deep work in these smaller pockets of time. She needed the sand to not be frivolous and unuseful, so she’d started taking 5 to 15 minute blocks extremely seriously. Very seriously.

And to make sand strategic, she, said, she had to rebrand it.

She called her new, small, hyper-effective blocks of time Pebbles.

Pebbles weren’t rocks, but they certainly weren’t sand. They were substantial. They moved her forward.

The key to Pebbles, she said, were the transitions.

The reason the default when you had five minutes to work on your startup was to answer emails was because answering emails was the easiest thing to transition into and out of. You could pull up emails, answer one, and get back to your life with zero friction. Same with social media, imessage, whatever.

So, she built a system that focused on transitions. Being able to go from ordering your Starbucks to 7 minutes of deep work while they made your latte and out again.

The start of that system was to pick a big, hairy, intimidating topic she’d naturally been avoiding, and to break it down into 5, 10, and 15 minute tasks every Sunday. Those tasks were put into her notes app. It was critical, she said, that all those 5, 10, and 15 minute slots of random time throughout the week were focused on the same overarching task or theme. This pulled them together into a bigger block in her mind. Her subconscious would work on them in the background. If her pebbles jumped around from answering emails to social posts to marketing to sales, the system crumbled.

At first, she said that she’d picked stuff she liked doing for the Pebble focus. But she realized a much better approach was to pick stuff she hated for these blocks of time. That allowed her to use her uninterrupted Stone time, every Sunday morning from 6-10am, on something she enjoyed.

She also said she felt an enormous sense of pride when she’d spent a random 10 minutes doing something that made her uncomfortable.

She also noted how important scripting the first part of any task is. If you’ve got five minutes, you can’t spend 3 minutes figuring out what to do. So, each 5 minute task had a very clear “start by doing X” to accelerate that transition.

The end of each 15 minute session were scripted, too. The prompt before you moved on was always a prompt like, quote, “end the task by noting the next step you need to take and what you need to think about until the next five minute block.”

I reached out to her for this episode to see if she still did this, and she said absolutely. I asked what her current Pebbles were focused on, and she said sales. Always sales, these days.

Figuring out pebbles has been, she said, the most important part of her business.

And it is an amazing example of one of my favorite approaches in life: Notice something overlooked but important, and take it extremely seriously.

—

Your Subconscious

A quick note on the subconscious before we jump into how to build your own 5-minute list.

I’ve talked about this before, but your subconscious loves a job. An open loop. It’s called the Zeigarnik Effect - basically, that we remember unfinished tasks much better than we remember finished ones. Your brain is antsy and hates when things aren’t settled - it’ll work on loops in the background until they’re closed. It’s why you remember every detail of Pachinko while you’re reading it but couldn’t tell someone the plot two weeks after you’re done.

Your brain also likes structure. X is for Y.

So, when you set up 5 minute lists, your brain will be working on those tasks in the background while also searching for the X for Y opportunity. It’ll search for five minute pockets. It’ll be more excited to work on this open loop. You’ll stitch together these disparate blocks into something way more similar to a Stone than sand.

The five minute list goes with our natural inertia. It swims with the current.

Now, let’s implement it:

Part 2: Building Your Five Minute List

A quick note on the name of the five minute list. I like it. It’s catchy. But practically, you should build tasks for 5, 10, 15 minute slots. And, maybe you’ll see that this expands all the way up to scripted hours. It’s flexible and up to you.

If you convert two random 15 minute blocks of time each day, you’re adding 3.5 hours of startup work to your week.

You can’t afford to not do that.

So, let’s get started on specifics. I’ll be the guinea pig.

The high-level steps are:

1. Pick the topic you are uncomfortable with but, when you write a story about your success in 12 months, plays a massive role.

2. Write out a longform, descriptive version of that success

3. Feed that into your favorite AI with our set of prompts

4. Translate it into a part of your weekly reflection

On we go.

Step one: Pick an uncomfortable thing you need to do to be successful.

Luckily, this one will probably jump out at you. It’s the obvious one, don’t overthink it. For me, this is podcast growth.

I love that the pod has grown organically to this point - that everyone listening right now probably got a rec or saw a post somewhere. You're here of your own valition, this isn’t a shotgun wedding.

But, when I write my story of success in one year, I need there to be, like, three times as many of you. Maybe five. Ideally 10. That drives everything. So, it’s time to push on it a bit. And sure, if you wanted to leave us a 5 star review and refer this to a friend, I’d be thrilled. But I need a strategy. And the 5 minute list is the perfect place to create one.

So, the Five Minute list will belong to: Podcast Growth. I avoid any serious strategy around it to protect myself - I put a lot into this and I’d be upset if people thought it was bad. That’s something an amateur does, not a pro. So, podcast growth is the focus.

Step two: Write out, longform, what success looks like.

For me, that includes who is listening, what problems we help them solve, why they’re so excited about it, and why it’s obvious they should share it.

I won’t read this whole paragraph now, but it’s important you type it out. Spend some time on it. Describing success is hard, and, luckily, this will be an iterative process, as you’ll see with the next step.

Once you get that success paragraph, you hit step three.

Feed it into your favorite AI. I’m a Claude guy at the moment, but I know people like chatgpt and whatever else is popular when you listen to this. I think they’re all basically the same, especially for something like this.

Copy paste that paragraph in, and explain to the AI what you’re trying to do.

Here’s how I started:

Quote, below is my definition of success as it relates to Podcast growth. I’m looking to grow the podcast in a bunch of targeted ways, so, could you come up with 20 ideas that would hit the audience I’ve described? Note - I don’t want to have guests on the show and I don’t want to go on other people’s shows. I want hub and spoke strategies - ways to grow through hubs that have organized my customer’s already.

It gave a decent answer, but I kept pushing. I asked for 40 more examples, then 40 more, asking it to think about how other businesses in other industries grow. I added boundaries - approaches I liked that it should dig deeper on, and others I didn’t.

I ended up with a list of 10 strategies that matched what we do and how we’ve grown in the past.

Then, I asked Claude to break this into 15 minute tasks, complete with a sentence on how I should get started. I’d explained the whole sand and stones and pebbles thing, and Claude, not surprisingly, gets it. I added a bunch of current tasks to show exactly how I like things broken up.

We went back and forth a few times, but landed on a set of tasks I like. I then exported them to Notion.

And now I have 10 strategies, broken up in 15 minute chunks, that I can attack in the margins over the next few months. My random slots of time are owned, entirely, by podcast growth. And I love it.

The first strategy was to reach out to college entrepreneurship clubs. I’m a few weeks into executing on it in the margins, and pod growth is noticeably up.

The End: Coworking

Entrepreneurship is incredibly lonely.

Both the fact that you’re doing it alone, but, maybe more, the fact that if you don’t do everything, it doesn’t happen. The work itself is lonely.

This is the biggest shift from being a non-entrepreneur. The sheer weight of the required proactiveness. And it’s not just that if you aren’t proactive good stuff doesn’t happen - if you aren’t proactive bad stuff happens immediately. Your good work is undone. Entrepreneurship isn’t just pushing a rock up a snowy mountain - it’s doing it with skiis on. When you stop pushing you start sliding backwards.

I’ve always tried to help founders find other founders to combat the actual loneliness side of entrepreneurship and with freelancers or folks off fiverr for the work loneliness side.

AI has changed the second.

It isn’t going to be some “her” level companion. But it is going to do work for you, for free. Write out a story of what you want done and have it put it into chunks that fit your workflow and work style. The work gets less lonely.

The five minute list is a thing that always works. Flip your random scrolling and email answering to targeted work on a hard problem you need to solve to grow like you’re capable of. Do it twice a day and your business will chance.

It always works. That’s why it’s on the list. And lexington pennyworth the fourth, isn’t.

Beat it, chap.

This was the idea to startup podcast brought to you by tacklebox. If you’re stuck on customer interviews, join our kicking off customer interviews workshop. Head to gettacklebox dot com slash workshops and sign up.

Have a great week