There’s a fun game entrepreneurs play over drinks: 

Imagine starting over, totally from scratch.

With nothing.

Probably in an unfamiliar country or something. 

You have zero access to any of the capital or physical resources you have now.

You get to keep everything that’s already in your head: All the experience and hard-won learnings. 

But that’s it.

How long would it take you to get back to where you are today, success-wise?

People like to imagine that the Richard Branson or Elon Musk types of this world would wake up unrecognizable in some exotic place and immediately concoct a scheme. They’d figure out some re-brand, re-selling of bananas (or whatever).

Within a week, they’d be being driven around in a Rolls Royce. They’d be wearing a five thousand dollar suit. They’d be hailed by the locals as an entrepreneur genius. 

Or so the popular wisdom goes. 

I’m skeptical. 

I think there’s one important question to ask about this game:

Do you get to take your Rolodex with you?

If you were to really “start from scratch”, do you get access to that mentor who set you on your path when you were young? 

Do you get access to that first boss, who taught you everything you know about X?

Do you get that first client who unknowingly financed your first website… the website that landed you your second client… 

You get the idea. 

You can’t really remove entrepreneurial success from the environment it happens in.

An intricate and invisible web of social, psychological relationships weaves around you. It lifts you up and is as much a part of your success as your attitudes and thinking. 

Entrepreneurs struggle when they operate from a place of total entrepreneurial isolation.

The internet enables more people to build small – and large (but decentralized) – businesses from home than ever. The side effect of this? Entrepreneurs are more disconnected than ever before in history.

It is now absolutely normal for a business owner to operate from home and only socialize with “civilian” 9-to-5er friends, or – at best – people in wildly different businesses to theirs. 

The days of spending your time in close physical proximity to the people you’re accountable to – as an entrepreneur – are over.

This is problematic.

Isolation makes entrepreneurship harder than it should be.

This is why – if you really were to start over from scratch – your results would skyrocket the second you got someone in your corner. Genuinely support does tremendous things for the entrepreneur brain.

To drop into any situation and show up immediately as a focused, high leverage, execution powerhouse… requires help: Business success requires other humans to activate your social-primate brain that, in turn, motivates and focuses you. 

The first thing Richard Branson would do if were he dropped (unrecognizable) into Marrakesh with ten dollars in his pocket… would be assembling a team. 

You’re not supposed to do this by yourself. 

The bad news…

… is that making Good Decisions is the only way that entrepreneurial success happens. 

Things like product-market-fit, the right timing, great investors/mentors, assembling a phenomenal team and access to capital all matter, too. But these are all downstream consequences of Good Decisions being made by the entrepreneur. 

It’s all on you. 

The only way to make Good Decisions is to have the experience to know good from bad. This is why entrepreneurs become serially-successful. The more you know, the easier it gets. The rich tend to get richer. Success begets success. 

The good news…

… is that making Bad Decisions creates experience. Making Bad Decisions often creates the best kind of experience. Because entrepreneurs learn better when they have scars to serve as reminders. 

Bad Decisions – executed with conviction – create experience.

Experience trains you to make Good Decisions.

Good Decisions lead you to success. 

This means that the door to entrepreneur success is still wide open… For anyone willing to find the courage to execute on their Bad Decisions. And for anyone with the tenacity to keep pushing through that uncomfortable “experience” part. 

The good news is that the opportunity hasn’t gone way. The even better news is that fear, perfectionism and most people’s inability to focus… is keeping the playing field relatively empty. 

One in three Americans dream of starting their own company. But only a tiny fraction of those have what it takes to act on their bad ideas such that they find their way to a good one. 

  1. Connect with the beneficiaries of your passion.  The people whose lives your work transforms when you do it best. Your customers. They’ll remind you why it matters.
  2. Take a deliberate, outsized break. Absence makes the heart grow fonder and getting distance on something you’re stuck on tends to make the brain sharper. Sometimes stepping away – even when it feels like a failure – is exactly what we need to want to create again.
  3. Start something new. A lot of people confuse novelty for passion. If you find that doing something new ignites a new passion, the lesson may be that it was novelty all along that was fueling you. Sorry, but it’s better to know.
  4. Absorb the work of the masters. Whatever your field, there’s someone (or several someones) whose work dwarfs yours. This is a good thing. Soak it in. Revel in what’s possible.
  5. Write down your rationale. Don’t assume you’re totally mentally aligned on the significance of your thing. Don’t take your motivation for granted. Articulate it. Tease it out. Write down why you want to do this. Express it such that a toddler or a layman would understand why your thing seriously matters. Chances are you’ve forgotten, or weren’t sure in the first place. Doing the work of articulating your Why fixes that. 

Entrepreneurs constantly feel like they’re not doing enough. 

And when they have a super-productive day, they still feel as though there’s hundreds more tasks and projects remaining. That they’ll never be done. 

Then there’s the worry that you’re prioritizing the “right” things! 

All of this suggests that to live the entrepreneur life is to live with a constant baseline of productivity anxiety. 

It doesn’t have to be this way though. There’s a simple ritual I’ve cobbled together over the years – and rigorously road-tested – that clears the head, eliminates worry and sets up the week for clarity and focus. 

Most importantly this ritual unlocks confidence. It allows you to dive into your work week without second guessing yourself. 

It stimulates a level of extraordinary focus, effectiveness and flow that’s totally free from the anxiety that you are somehow not doing or being enough.

1. Evaluate the last seven days

The best predictor of your future behavior is your past behavior. 

Your optimistic goal to make the next week a journey of revolutionary self-growth… are great. But in reality, your focus and effectiveness will only improve incrementally at best. Usually it’s an imperceptible change week-to-week. 

Staying organized and reducing anxiety demands realistic expectations. It’s worth considering that a measly 2% improvement in “productivity” (however you measure it) week on week means that you’re doubling your personal effectiveness each year.

That’s why the best way to get a clear sense of the week ahead – what to expect, how much to push yourself etc – is to make an honest appraisal of the immediate past.

Scrutinize the following:

  • The total number of hours you spent doing the important-not-urgent creative labor of working “on” your business (not “in” it) 
  • What you accomplished, as a ratio against what you set out to accomplish 
  • The quality of your life in general: Did you also fit in the alone time, family time, sleep and play (un-constructive, sense-of-self-losing joy) time that you desire? 

Grounding yourself with deep and honest self-awareness of how you’re spending your time is the key first step to planning and beginning a highly focused and effective week with confidence. 

2. Perform the magic of non-scheduling 

Obsessive, hyper-anal scheduling and color-coding of tasks is a dangerous game of self-deception where personal organization itself becomes a form of procrastination. 

Keep your calendar minimalist by only scheduling events where you’re socially accountable to show up. That means your schedule is exclusively phone calls or in-person meetings. 

This should leave you with a series of blank spaces on your schedule. (If it doesn’t, you’re being a manager not an entrepreneur. Fix that.) 

It’s in these lusciously vacant non-scheduled windows that entrepreneurs do their best work. These are the times you can sit down and perform the creative, meaningful work as an architect overseeing your business. This is when the courageous projects that create exponential growth happen. 

Think of this blank space as a time to set appointments with yourself. It’s the time to work on the things that no one is making you do, but which will change the game entirely if you make yourself do them. 

I work one to one with some of the most extraordinarily successful startup-founders and entrepreneurs in the world. I can tell you that most of these high performers are only averaging between two and four hours of this type of work per day. 

Meetings, urgency and reactive firefighting are all realities of business. The more you succeed, the more you’ll be challenged by them. In some ways entrepreneurs always rise to the level of their own incompetence: They succeed and their business keeps growing… right up to the point where they’re no longer able to delegate the busywork. 

The minute you start clocking full days of reactive labor, you’re no longer an entrepreneur – you’re just doing a job in a business you also happen to own. 

Consequently, the key to never letting busyness – a.k.a. success itself – defeat you is in always finding time to move the needle on the important stuff. 

Creating windows of non-scheduled free time for your entrepreneurial mind to create within… really is a form of magic. It has to become a sacred ritual. Successful entrepreneurs treat this time in their schedule with a reverence bordering on the religious. 

You should too. 

3. Decide the priorities 

The final piece of the puzzle is to ask yourself what you’ll focus on, now that you have time ahead of you and the self-awareness to make it count. 

At Commit Action – where we provide a facilitated accountability service that does these three things for you – we intentionally limit our clients to three committed tasks each week. These are the prioritized projects you’ll work on in the windows of time you’ve carved out.

We demand that these commitments meet the following four criteria: 

  • Important and NOT urgent – The best business growth comes from actioning those big “some day” ideas sooner, rather than later. 
  • Working on the business, not IN it – The definition of entrepreneurship lies in creating businesses bigger than oneself. Everything else is just freelancing. 
  • Growth Driving Activity – The work must have a direct or proximal effect on driving bottom line (profit) results. Top line is often better. 
  • Courageous – Simply put, the best ideas are often the scariest ones. Businesses rocket forward because of founders with vision. 

The secret to getting into powerful flow-states is not deciding moment to moment – or even day to day – what it is that you’ll be working on. 

That’s why the most important ritual you can perform once a week is that of pre-decision. Setting up in advance your priority project plan frees you from the cognitively draining task of figuring out what to work on. 

When you sit down on any random day with (ideally) a three hour stretch of time to create… you can spend it creating, not exhausting yourself mentally by deciding-what-to-create. This distinction only appears subtle to the people who haven’t experienced the clarity that pre-decided priorities creates. 

Productivity Anxiety…

… Stems from our tendency to step out of the act of passionate creating itself and into a state of meta-analysis. It’s thinking-about-working instead of working. 

We stop what we’re doing to think about if we’re doing it right – or doing the right things – and the magic is lost. 

The confidence of realistic expectations – informed by honest self-awareness – allows you to stay soothingly on track. No more mini-panic attacks when the clock hits 5pm, prompting you to wonder where all the time went. 

Reverently creating the space you need to do meaningful creative work – and pre-deciding what it is specifically you’ll do with that space – then cements your flow state. 

This whole three-part process is a single once-per-week meta-analysis ritual. It’s the “single” part that matters.  

You should only do this once a week. 

Instead of oscillating anxiously (and frequently) between working and thinking-about-working, this ritual creates an ideal time and place for that (necessary) thinking. It doesn’t matter when you do this: Monday morning or Wednesday lunch time will both work. So long as you’ve committed to a dedicated, one time weekly ritual.  

When you have this in place, the ritual draws a clear (and absolutely necessary) line in the sand that reminds you that execution is everything: That the analysis and thinking-about-working part, important though it is, must only be allowed a small fraction of your work week. 

Twenty minutes per day is all it takes to achieve epic product market fit.  

It’ll pour jet fuel into your new business. You’ll supercharge growth. You’ll laser lock on to the precise product strategy that guarantees effortless customer acquisition.

All it takes is this one simple ritual. 

 You don’t even have to be strict: Twenty minutes a few times a week is fine. 

The only catch – hard part about this tactic – is that it’s uncomfortable. It’s a little scary. 

Enroll people in what you’re building

The idea of Enrollment is a simple mental shift of perspective. It’s a re-thinking and re-defining of your ultimate objective as an early stage entrepreneur. The tactic that comes next, changes everything.  

I credit Seth Godin entirely for this concept.

He was the first person who helped me understand that the people my team and I serve at Commit Action aren’t just customers, they’re students. Reframing your customers as students is the key to understanding enrollment. 

A good teacher doesn’t just transfer knowledge to his students. He enrolls them in the process of learning itself. When a high school science teacher makes chemistry come alive to a class of bored, distracted, hormonal teenagers… when they sit forward on the edge of their seats to see what’s happening… that’s enrollment. 

And as entrepreneurs, we can do something similar in our businesses. And it changes everything. 

Enrollment is simply the idea that people have agency and the volition to choose what they focus on. Where your target market chooses to spend their precious attention, time and money is up to them. As an entrepreneur, rather than seeking out sales, market share or even leads… the goal is to enroll people in what you’re building. 

This shift in mindset can be applied in many ways, each more powerful than the last. Investors, mentors, joint-venture affiliates, partners, vendors, journalists, agents and more… can all be targets for the entrepreneur seeking to enroll the people who matter in what she is building. 

Enrollment busts through chicken-or-egg struggle

Most great business ideas hit up against a wall where a chicken or an egg must be produced, but the entrepreneur has neither. 

We need to attract advertisers to the platform to pay for building it, and we need a fully fledged platform to attract users. But we need users to attract advertisers. 

Chicken vs egg. 

Businesses always need to be jump started. Especially bootstrap ones. The extra juice comes from people who aren’t customers (or aren’t just customers) but who’re also key stakeholders who get invested – often merely emotionally – in seeing the company succeed. 

It happens in that moment when a mentor introduces you to someone in their trusted inner circle, who becomes your first client. Or when a bigger company takes a risk because they believe in what you’re doing, and says “Yes!” to integrating your thing.  

There are too many examples to list. The key is understanding that none of this happens without the concept of enrollment. 

How to get people enrolled in what you’re building 

Enrollment happens when you seek out and build relationships with the key stakeholders who can jump start your business. 

Here’s a little secret: People LOVE to be involved in early initiatives and are flattered when they’re asked for advice. Those two principles will aide the goal of enrollment. 

1. Early adopters are enrolled:

People will want to be involved in an early startup, particularly if it’s subtly suggested/implicit in there being some early-mover advantage to THEM. “Startups” (even when they’re bootstrap ones!) are so fetishized by society right now that you can often get people excited to connect, to chat, to grab coffee just so they feel involved/important/significant. 

Use this. 

2. Asking for advice is asking for enrollment: 

There’s an old saying in business: 

“Ask for money, get advice. Ask for advice, get money.” 

Almost every human being is flattered when they’re asked for advice in this context because of the implication that they’re a person of note in the industry, that their thinking will be valuable in shaping a new business. 

In actually giving that advice, they mentally/emotionally enroll. A side effect of that enrollment makes them more likely to actually use/participate-in the very product being created. 

These two approaches work for your list of valuable-people-to-enroll that’ll jump start a business. 

It also works for actual customers. 

Customers are arguably the most important people to enroll in your vision. A customer is just paying you for a product or service. They often walk away – even after spending money on your thing – without a second thought. But when a customer is enrolled, something altogether different happens… 

An enrolled customer feels an emotional connection to the business

They’ve got a stake in it, if only mentally. They tell people. The product or service is a part of the story they tell themselves about what kind of person they are. They feel like an insider. 

You’re enrolled at your local coffee shop where they know your name, your order, what you’re working on and where you went last weekend. Even more so when you – as customer – know all these things about your barista. That’s enrollment. 

Enrollment treats the customer as a student

To enroll someone in your business is recognizes their innate curiosity. It’s going a little further, telling a bit more of the story, showing a bit of what goes on behind the scenes. 

The barista at that coffee shop will – if he’s smart – pour you a tiny sample of pour-over from those artisanal shade-grown beans they’re trialling. It’s not on the menu, but he wants to know what you think. It’s a tiny gesture and it’s a story. 

What it’s really about is having you enroll yourself in what he is building.  

Enrollment is everything 

A good friend of mine built a training company teaching people to bootstrap software business ideas – from scratch – by enrolling executives to collaborate on designing solutions to their problems. Those collaborators become first (and lifetime) customers. They fund the development of the actual software. 

It’s a brilliant, lean process to arriving at powerful product-market fit. It breeds a fanatical customer base. 

What I like about the approach is that it hinges on the idea that enrollment is the first step. Before you even have an idea, reach out and start talking to people. Get to know their work and lives. Empathize with their problems. Get them enrolled. Only then should you start to build. 

The other powerful thing about this approach is that once you begin a relationship, the best thing you can do to continue it is to stay in touch by updating them on progress: 

“Hey, we’ve published a simple MVP website for this. Here’s a link. Would love to hear any initial impressions!”  

“We’ve just gotten an offer to work with X, what do you think of them?” 

“Hey our first offering is live, check it out!” 

It’s not that you need input from your mentor/customer/investor on all this stuff. But the more you invite it,  the more crucial points of contact you create. 

Direct sales gurus say that “five to seven points of contact” are required to build trust and close a sale. What they’re really getting at is enrollment. It’s not about points-of-contact, it’s about turning strangers into collaborators, comrades and students first. Then, when it comes time to find the customers (or resources) you need, they’ve all been waiting for you. 

The simple ritual I promised at the start of this article is to just spend twenty minutes a day thinking about who you’re seeking to enroll in your vision, and how you’re doing it. Reach out, connect, educate. It doesn’t take long. 

The real goal is to retrain your entrepreneurial brain not to think about sales, conversion rates or revenue. Instead, make enrollment en masse – of everyone that matters – your ultimate objective. All those specific results (and even product-market-fit) will follow. 

Enrollment makes everything easier, faster and better. 

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