The Nuts and Bolts of Creating A Business You Love

Building a new idea or following a dream? Here’s how to practically do it.

I work with a lot of people who are trying to create something that they’re passionate about, or trying to craft a unique lifestyle or business model that works superbly for them.

Some are looking to create a classic startup or small business, while others just want to build an independent part-time income stream.

Many want to monetize something they love doing, diving into uncharted territory to “product-ize” or “service-size” a unique capability that doesn’t have a classically established market and perhaps isn’t even clear to articulate.

I end up mentoring a lot of people who have taken various of these paths. Whichever yours is, here’s a practical utility guide to some techniques that seem to be common to all of them.

This article is long, so here’s a table of contents:
1. Give yourself permission to not define what you’re doing.
2. Move in thousands of concrete iterative experimental steps.
3. Manage your “spoons” like resources. Your energy is your capital.
4. Also manage your resources like resources. Strategies for using money and social capital.
5. Some useful self-reflection checkpoints. Questions to ask if you’re stuck.
6. Final notes.

1. Give yourself permission to NOT define what you’re doing.

(If you already know exactly what you’re doing, just skip this section.)

The line between a clearly articulated vision and an inchoate sense of approximate direction is surprisingly blurry. In a world filled with stories about following your dreams, there can be an enormous amount of pressure to give a crisp definition of what exactly the dream looks like.

Create a clear value/purpose statement, the advice goes, and all the other answers will fall into place from there.

This approach works for the 10% of people who can do that. But the truth is that the vast majority of people I talk to who feel a strong sense of vision actually have a lot of uncertainty over how to pin it down to a single clear offering description.

Some have an intuitive sense of direction that can’t be put to words. Others know they’re searching, but haven’t found the answer yet. Still others feel pulled in five directions at the same time.

All of those are totally great. After all, the vast majority of people who end up building an effective and fulfilling business don’t end up with the thing that they started out searching for. Some had to create a thing where none existed before. Others had to explore, iterate, and grow their understanding of the world and themselves first. Still others feel they are living their dream, and do so in a way that defies description.

Many people simply have multiple dreams at the same time, and find a way to live parts of each of them in a unique combination.

Ultimately a clear purpose or value statement only matters as a tool to help you achieve something you want. If you can come up with one easily, great: that means that you got a very useful tool with low effort. But if the pressure for clarity makes you feel like you can’t even truly get started until you have it — or worse, feel like a failure — then it’s clearly not the right tool in the moment for you.

Identifying our vision and how to describe it is simply another lengthy part of the journey. Some people are lucky enough to knock that part out early, but it’s also fine to take decades, or more. Your vision a fluid thing that evolves with you, like your identity or tastes.

This goes especially for people who feel driven to build services — I see so many would-be service providers trying to narrow or shoehorn themselves into an offering description that feels the most “accurate” to an invisible standard. Then they spent months trying to characterize the thing, prove its value and qualifications and make a coherent website and business name, and get lost in the process.

In practice, in most of these cases for services you don’t actually know what the final form of the service you offer will be: forcing yourself to commit early will just waste your time and make everything 10x harder.

Instead, just try to manually get a dozen vaguely related gigs as quickly as possible, using whatever description is appropriate for each client: the only way you’ll know how to talk about your value and identify what works for both you and the client is through experience.

After all, language grows with society. If you want something you can’t easily put words to, chances are we just haven’t invented the words for it yet.

Maybe doing that is your job.

2. Move in thousands of concrete iterative experimental steps.

So what does making your personal-passion business happen literally look like from day to day?

When you break new ground, you will probably have no idea how to literally go about it. After all, if you did, it would be old ground.

But you perhaps have some educated guesses. Or some wild guesses. Or some dumb, unsexy guesses. Or some dissatisfying guesses that you know won’t work so you feel stuck because you don’t have any better ones.

All of these are great, even the last type. By the time you’ve got an idea or five, stop guessing and move on to the next step:

The main work of breaking new ground and creating your business is NOT coming up with a single great idea and then executing on it like mad. It’s trying dozens of things, each as effortlessly as possible, and constantly adjusting/adapting after each one.

Every new thing we try deepens our understanding of the world and of ourselves by an entirely new dimension. Even if we just do a quick mediocre job of it, our understanding will still be deepened, almost as much as if we do a perfect job. As a result, it’s critical to embrace doing lightweight, mediocre jobs on the first few dozen versions of an idea we want to try, because we need understanding far more than we need perfection.

Ultimately, if you feel like there’s a different way of being and living out there in the world that you’re seeking, two things have to change: you, and the world. Iteration allows these two components to find each other, and meet in the middle.

(Want more specific tactics for experimenting & iterating? Feel free to hit me up at Prototype Thinking Labs.)

3. Manage your “spoons” like resources.

If you haven’t heard of Spoon Theory, the basic idea is that we can measure our most limited internal resources by units of “spoons”. (They’re called this because the person who first invented it demonstrated the concept with a handful of cafeteria spoons.)

For example, as an introvert, I only have maybe 2–3 spoons a day for socializing. Or, my easily-overstimulated friend might have to burn continual spoons just to be in a loud, bright place. Or perhaps writing costs you a lot of spoons, but doing research is “free”. (The numbers are arbitrary, you can use them if they’re intuitive to you, or just use categories like “a little” and “a lot”.)

Each of us has a unique internal resource profile with

• types of activities that come easily to us and types that are expensive in terms of energy use (aka spoons)
• types of physical and mental energy that can be directed toward those activities
• different activities that help us regenerate different types of energy
• different times of day or physical environments that are ideal for certain types of energy or activities

Your unique profile is the hand that you’re dealt, the internal resource structure that you’ve got to work with to be productive and achieve your goals. If you have other sources of strain, such as physical or mental health needs, major personal obligations, or ongoing stressors, those all factor directly into your resource profile.

For some reason, we get taught this fatal myth that we’re supposed to be able to have arbitrary amounts of productivity of all kinds at all times, and if we are having a hard time we should just push ourselves harder. This moral pressure leads us to exploit our internal resource landscape exactly like humans have exploited the environment.

Instead, manage your internal resources like any other type of resources:

a) Think about whether the type of energy you’re using is efficient.

Eg, commuting around the city exhausts me, so I started doing sales meetings on the phone. Even though this was only 60% effective toward a sale, I could do 4x more of them.

b) Make a plan where the bulk of the work involves doing things that come easily.

Eg, I realized that, even though it seemed high-production, I could give workshops in my sleep — it’s easier for me to give a workshop than nearly anything else. So I switched to running as many experiments in the form of workshops (rather than, say, writing or landing pages) as possible.

c) Only spend energy types that you’re short on in really vital places.

This is the single most important principle. Eg, casually hanging out and talking or drinking completely exhausts me, so I stopped attending networking events and saved my social spoons for high-value 1:1 catchups with key networking contacts. Then I hired someone who is great at wider networking.

d) Think sustainably: Don’t burn more of your resources than you can generate back, and make regeneration a part of your plan.

Eg, I know that I’m energized by coaching others, especially entrepreneurs who are just starting out. So I reserve a certain amount of time each month for pro-bono coaching even though it comes with no material benefit.

e) Think regeneratively: Challenge yourself to create a plan that gives you more and more of your most limited resource over time.

Eg, clients have often found that forcing themselves to practice physical self-care, or to spend time in the company of loved ones, quickly pays for itself in terms of time and energy.

f) Don’t be deterred if this means that your balance of activities is totally different that what you’re accustomed to, or what others do.

Give yourself permission to optimize your energy in a way that works for you. Eg, a good friend is famous for her ability to create a sense of peace and beauty for clients. She realized she needed 2–4 hours every day of sipping tea and peaceful walks in order to enhance that sense of inner balance in order to be able to share it with others, so she considers those activities as a central part of her workday.

Spend the time to sit down and make a list of what activities that you often have to deal were are cheap and expensive for you. Then build your experimentation plan out of the cheap ones.

Much more often than not, if we’ve been procrastinating something we care about, it’s just because we’ve set ourselves up to do it the expensive way.

4. Also manage your resources like resources.

In addition to internal resources, here are some common external resources that are likely to come up in your purpose-chasing journey, and how to think about them.

Money

Other than keeping you alive, there are three important things that money does.

1) It enables #2, experimenting. Remember how we said to try tons of things relatively frictionlessly? Frictionless means very low effort and very low cost to start out. Do NOT spend a significant amount of money (say, over $500 — $1000) building anything that you have not tested at least a dozen times. Most things can be tested for under $50. Challenge yourself to come up with a way to test it for under $50 (or whatever your budget is, but keep it low).

2) Money improves the plan you made in #3, managing your internal resources. You can use money to supplement your most limited internal resources by paying for help or things that regenerate you. A major budgeting mistake I see people make is financially undervaluing their most limited internal resource. If you’re serious about optimizing internal resources, it can also help to have a discretionary budget to help facilitate on-the-fly internal resource shifts.

For example, one of the single best and most common versions of this that I’ve seen is hiring a house cleaner.

3) Most obviously, money will be necessary for actually executing your precise longterm plan, once you know what it is. If you’re an entrepreneur, this may be the MVP of your product. If you’re exploring, this may be your first serious draft of your path. Spending serious money on something does not make it any more likely to be the right answer: don’t pay for this until you have experimented on it a few dozen times to be sure.

Time

When breaking new ground, we go through this lengthy period of uncertainty, and it’s easy to get really overwhelmed by how much time and effort everything is going to be. The first few things you want to try, which you know probably won’t work, will already take so much effort; how will you ever get far enough?

The answer is, don’t stress about this: the most difficult and time intensive part of the work you’re doing is right now, right at the beginning. Your progress will look like a hockey stick — it’ll take 80% of your total effort to get the first 20% of the way, and only 20% of your effort to get the other 80%. So if things feel ridiculously slow, chances are you’re progressing right as you should to be.

But — speed things up with more experimentation — challenge yourself to try an idea using under 2 hours of work.

The biggest mistake I see with use of time is NOT investing time in running experiments before diving into a big plan.

Social Capital

Social capital is our karma with other people. It’s called social capital because it’s meant to be spent. Because it feels like our credibility and reputation is on the line, we often want to be overly careful about using it for anything, and prefer waiting until we’re ready with final drafts.

It doesn’t actually work that way, though. Instead, the more things you try out in experimentation mode, the more social capital you will build up.

The single biggest mistake I see people make anywhere in this ENTIRE process is not spending social capital hard and fast enough at the beginning of their journey.

Unlike money, it’s totally okay to invest 80–90% of your social capital into your first 2–3 projects (or 3–6 months) — doing this will drastically accelerate your learning and perspective, which is the most important return at that stage. There will always be more coming in later. Accept that you will inevitably make a fool of yourself with a bunch of people you currently respect and need, and do it anyway.

Another unintuitive fact about social capital is that you don’t build it primarily by doing things for other people: you build it primarily by having other people do things for you.

There are a number of psychological processes behind this, but the short version is that the more people help you, the more engaged and committed they will be to what you are doing. For most people, the top motivator is actually feeling valuable / valued and significant, not getting something for themselves.

Spend social capital immediately and profusely, and I promise it will regenerate in no time and you will save yourself 2–5 years of grief.

Physical Environment

Your physical environment is a critical component in shaping your habits. Everyone subconsciously reasons about what their options are based on available possibilities and cues in the physical environment. Put some effort into making your physical environment supports your internal resource expenditure plans and helps you build the habits you want. Give yourself a small but nontrivial budget for this, and spend it with your internal resource profile in mind.

Social Environment

Your social environment is even more critical in shaping your habits than your physical environment. Whether you want them to or not, the people you see regularly feed you a constant stream of content that you process and adapt to. So managing the types of things that get shared with you by others is one of the best ways to influence your overall thoughts, feelings, and habits.

5. Some useful self-reflection checkpoints

When venturing into the unknown, one of the most difficult (and stressful) challenges can be figuring whether you’re wandering-freely-but-actually-productively-on-track-in-a-deeper-sense, or actually-totally-unhelpfully-off-track-and-wandering-aimlessly.

If you ever find yourself feeling uncertain and want a checkpoint, here are some questions to ask yourself:

i) Have I been spinning my wheels on the same problem 3 or more times?

If you find yourself thinking through the same problem and cycle of non-answers 3 times in a row, or working on a problem for more than 2–3 hours without an answer, run an experiment using less than 2 hours of work. There is surprisingly little difference in outcome between spinning your wheels for 3 hours and doing it for 3 years. It means that you’re in a trap of trying to make guesses without enough understanding. The only way out of it is to go and get more understanding through trying something out.

ii) What is the thing that I don’t know?

You might be surprised how often most of us simply fail to directly identify that we don’t know something and confront the thing we’re uncertain about. Instead, we often try to cover for it, work around it, ignore it, “fake it til we make it”, or hope that by working harder in other areas the issue will become obsolete. But once you have a clearly articulated unknown or question, it just becomes a simple matter of going out and doing some experiments and research to find the right answer.

ii) Is there a nagging uneasy feeling that I’m avoiding?

A more broad version of the above: If you find yourself avoiding something — a task, a topic, an idea, a direction — because it makes you feel naggingly uneasy, that means there’s something really important and useful there. If it wasn’t important, it wouldn’t keep coming up. The fact that it does means that some part of is connected to where you are at right now. The fact that it’s uneasy means that on some level you know you might actually be able to address it.

Muster your courage and dive into it. It will be the most productive possible thing for you to do, even (especially) if the connection seems unclear.

(Note that this doesn’t apply for uneasiness-due-to-known-triggers. It’s not that sort of uneasiness.)

iv) Is there a nagging inconvenient / stressful feeling I’m avoiding?

If you find yourself avoiding something not because it makes you feel unsettled, but because it makes you feel overwhelmed, stressed, or guilty, this is probably because tackling it exceeds your available spoons.

Instead of pushing against the wall, assess your internal resources and costs, and make a plan to tackle it in a sustainable, bite-sized way.

(Not every unpleasant thing has to be internal-resource-optimized, some things should just be powered through. But if you’ve gotten to the point of consistently avoiding it, that means willpower is not the answer.)

v) Am I chasing the presence of something or fleeing toward the absence of something?

Are you trying to make something you like be there, or make sure that something you don’t like will definitely not be there? Also known as, is your goal actually a real thing that can exist, or an eternally-moving signpost?

It’s possible to attain the presence of a thing, but impossible to guarantee that something will never happen. Often, however, especially if we’re responding to personal experiences, we may find ourselves wanting something that’s more genuinely expressed as an absence than a presence. This is a completely legitimate and important feeling, but it does not work as a strategic goal, because nothing will ever feel like enough.

Some common examples of this include:
- Creating community: Are you trying to empower a group of people through connection, or trying to never feel lonely again?
- Selecting product/service features: Are you trying to solve a particular problem for people, or trying to include something to address every possible objection to your design?
- Personal branding: Are you trying to communicate a value-add to others, or trying to forestall any possible source of inadequacy or insecurity?

If you find yourself pursuing an absence, instead ask, “What is it that I feel gets to happen once the thing is gone?” And then directly try to make that happen instead.

vi) Am I trying to help someone, or get that warm fuzzy feeling I get from helping someone?

For most people, helping another person in a significant way provides an unparalleled high. We feel connected, warm, relevant, significant, impactful, valued, and/or accomplished. Indeed, immediately impacting another person is sort of the most fundamental unit of mattering.

However, it’s important to recognize that the benevolence high in question is actually a fringe benefit. Optimizing for actual impact can lead to very different choices than optimizing for the high. (This is why people over-donate “fun” items like toys and condoms to disaster victims and under-donate money — there’s a stronger benevolence high from donating a specific item and imaging its use, and a weaker one from directly giving cash. But then there’s never enough cash for the critical things, and instead precious resources get used up handling the useless items.)

If you find that the pieces of a project keep not coming together, consider whether the core structure is based around genuine service. We all need benevolence highs to live and stay motivated and boost our internal resources — we just need to pursue them very responsibly. The line between service and exploitation can be a fragile one.

vii) Do I actually just need the help of an expert?

If you’ve already tried at least three independent experiments on your own and continue to feel like you’re not asking the right questions, it’s a good cue to seek outside help. Although, an expert won’t always be able to give you answers, they will be able to help you identify enough key questions and shortcuts to get you going again. The best time to benefit from an expert is after you’ve had the concrete experience of a few experiments under your belt.

viii) Am I being specific enough?

It’s easy to confuse a plan and an intention. A plan is concrete and so specific that you can literally visualize a chain of events unfolding in time and space, like in a movie. An intention is more like a set of evaluative criteria, traits that those events may or may not fulfill.

For example, if you decide to meditate every day, this is an intention. If you decide that you will meditate in the living room at 7am before you shower by sitting on the cushion that you keep next to the couch, this is a plan.

As another example, if you want to help young people get jobs, that’s an intention. If you want help low-income college students afford career-critical unpaid internships through creating a grant program funded by companies that may want to employ them in the future, that’s a plan. It may or may not be a good plan, it may last only a few hours before you change it, but gives you a start point to work from.

Plans are a thousand times easier to successfully execute than intentions, for several reasons:
- It’s easier to put effort into something if you know what concretely to do
- It takes a lot more cognitive work to generate content that fulfills a set of criteria than it does to riff off of an existing prompt
- It’s easy to tell if a plan is getting derailed and how, but there’s no way to tell if an intention is in trouble until it’s already failed. And then you still don’t really know why. For example, you could walk into the living room at 7am and find someone else is there, and know to shift gears. But you won’t realize you are having a hard time “meditating today” until the day is over, at which point it’s too late to make adjustments.
- You’re more likely to catch key flaws merely in the planning process
- You can keep adapting and improving plans based on outcomes, but intentions are perfect in their abstraction and can’t change to incorporate learnings and experience.

If you’re ever in doubt, make sure you have a concrete and specific plan. You don’t have to be wedded to it (that’s what iterative improvement is for), but the mere fact of having one will keep you moving.

6. Final notes

Ultimately, building something new takes time and a lot of trial and error. But there is no such thing as a false start: only many useful lessons toward solving a problem that no one has ever solved before. The more things we try, the more we learn.

Crafting a professional life that uniquely works for you begins with treating the unique way you work like it’s important. More than important: it’s the soul of the matter.

They don’t teach us how to do this in school, or stories, or other life-lesson-sources, so it’s actively important to challenge the ways we’ve learned to manage our resources, both inner and outer.

And remember…

If you feel like there’s a different way of being and living out there in the world that you’re seeking, two things have to change: you, and the world.

If at any given time you are moving on one or the other of these, you are bound to get there eventually. If you ever get stuck, just switch to the other one and keep on going.

(If you’ve found this guide useful, I recommend referring back to it occasionally, especially Section 5’s list of checkpoints when you’re stuck.)