The Side-Project Guide

Below are the four ways you can focus a side project.

P. Problem
Sometimes you start with something that frustrates you. You see an issue that keeps
showing up, and you want to understand its causes and whether people are willing to
pay to solve it.
Examples:

• Parents are struggling to find consistent after-school care, and the waitlists keep getting longer.
• Local service businesses struggle to hire and retain skilled people, which stunts their ability to grow.

I. Industry
Sometimes you are drawn to a field and want to understand how it really works. You
want to look under the hood and see how the business models operate, what drives
success, and where there may be compelling opportunities.
Examples:

• You want to understand how home-service companies work, the various ways they make money, and what separates the good ones from the bad ones.
• You are curious about the wellness field and want to learn more about the different business models inside it.

STEP 1: FOCUS, CONT.

C. Customer
Sometimes, you start with a group of people you feel a personal connection to and
want to support. You want to gain a deeper understanding of their problems, habits,
and unmet needs.
Examples:

• You helped your parents transition out of independent living and now feel drawn to supporting busy adults who are caring for aging parents.
• You have spent years around youth sports with your kids and want to understand the needs of families who are juggling school, activities, and logistics.

T. Technology
Sometimes you start with a technology you want to understand more deeply. You
are not trying to force it into a business idea. You simply want to learn how it works,
what is behind it, and where it is being used or tested today.
Examples:

• You want to learn how AI actually functions, from how models are trained to what makes them accurate or unreliable, and you want to study the types of use cases where early adoption is happening and where new experiments are emerging.
• You want to understand how biometric wearables collect and interpret data, which sensors they rely on, how the hardware works, and which measurements are trustworthy today compared to the ones that are still evolving.

The goal is learning, not deciding. By understanding the technology, you give yourself
the ability to later connect it to a problem, customer, or industry you know well.
Many great businesses start by combining a familiar space with a technology that
most people don’t yet understand.

PICT gives you four clean ways to define a focus. It’s okay that your focus starts

STEP 2: COMMIT

Once you have a direction, the next step is deciding how much time you can reliably
invest each week. You don’t need a lot. Even a couple of protected hours can create
meaningful progress. What matters is choosing an amount of time you can honor and
show up for consistently.

A lot of people believe they have no time. That usually isn’t true. It’s simply unexamined.
If you look at your iPhone’s screen time report, you might be surprised by how many
hours disappear into your phone each week. The same is often true for watching sports,
streaming movies, consuming news, or scrolling through social media. These activities
are not wrong, but they highlight an important point. Most of us have more discretionary
time than we think.

If someone you loved suddenly became very ill, you would find time immediately. You
would reorganize your life without hesitation. The issue usually is not whether you
can create time. It is whether what you want is clear and compelling enough to justify
making that time.

If you decide that exploring business ownership matters, you may need to reclaim small
pockets of your week. A few simple shifts can open up the space you need, such as:

• waking up twenty minutes earlier a couple days a week
• using a lunch break for focused work
• turning off your phone for an uninterrupted hour
• replacing an evening of television with quiet thinking time
• protecting one weekend morning for deeper work

These small adjustments can add up quickly when done consistently.

STEP 2: COMMIT, CONT.

Some people also find it easier to follow through when they are doing it with
someone else. A partner can create accountability and turn a personal intention
into a shared routine. Later in this guide, we will discuss how to bring an exploration
partner into your side project.

The primary purpose of committing this time is to give yourself the resources needed
to actually learn something. You are buying the hours required to understand a
problem, industry, customer, or technology well enough that real opportunities can
start to emerge. Without time invested, everything stays hypothetical. With time
invested, you begin to build experience, insight, and pattern recognition that can
eventually point to a path into business ownership that you are genuinely excited
about.

Along the way, commitment does tell you something about desire. If you struggle to
create even a small weekly window, that is useful information about your current
season. If you can make the commitment, even in a modest way, the learning that
comes from that time will do more for your confidence than any amount of thinking
about it ever will.

Commitment is how you fund the learning. Once you begin showing up each week,
you give yourself a real chance to discover what might be possible.

STEP 3: EXPLORE

Once you have a direction and the time to pursue it, the next step is to use that time
to learn. Exploration is how you move from curiosity to insight. You are not trying to
pick a business or make decisions yet. You are trying to understand your focus well
enough that real opportunities begin to surface.

A helpful way to structure this phase is the 20/80 rule. Spend about twenty percent
of your time reviewing what you learned, making sense of it, and planning what you
want to explore next. This is where you synthesize your notes, identify the questions
that are still unclear, and decide which people, environments, or small tests might
help you answer them. The other eighty percent of your time is the doing. Planning
keeps you intentional. Doing is what builds the real-world knowledge you cannot get
from thinking alone.

There are four main ways to explore. Most side projects include some combination of
all four.

• Field trips. Go see things in the real world. Visit businesses or environments connected to your focus. Watch how work gets done and how people behave. Seeing things firsthand always reveals things you could not have predicted.
• Interviews. Talk with people who spend their days in the space you are exploring. Ask owners, employees, customers, or vendors open, curious questions. Listen for patterns, surprises, and contradictions.
• Research. Study how the space works. Look at competitors or adjacent solutions. Review business listings or franchise materials. Read industry reports or articles. Research helps you understand the mechanics behind what you are observing.
• Experiments. Run small tests to learn something specific. Build a simple prototype. Create a landing page. Try a tool or process. Shadow someone for a day. A small, focused test can teach you more than weeks of speculation.

STEP 3: EXPLORE, CONT.

The interplay between planning and doing is what makes exploration effective. Each
week, the twenty percent planning window turns what you learned into your next set
of field trips, conversations, research tasks, or experiments. Exploration is iterative.
New information creates new questions, and new questions point you toward the
next people you need to talk to, the next environment you need to visit, or the next
small test that will teach you something concrete. When you build your activities on
what you learned last week, your understanding compounds.

As you explore, something important begins to happen. You start seeing
opportunities you could not have spotted from the outside. You may come across
businesses or franchises that clearly serve a real need and could be purchased or
licensed. You may uncover problems no one is solving well that could form the basis
of a compelling start-up. You may see existing solutions with obvious weaknesses you
are excited to improve. You might notice trends or underserved groups that hint at
where a meaningful business could be built.

None of this appears on day one. It appears because you put yourself close enough
to the space to see what is actually happening, and because each week of exploration
refines where you look next. Exploration replaces assumptions with firsthand
understanding. It gives you a clearer sense of which ideas energize you, which paths
feel promising, and which directions are not worth your time.

You do not need to explore perfectly. You just need to explore consistently. When you
use your committed time to get closer to the real world and let each insight shape the
next, you give yourself a real chance to discover what might be possible.

STEP 4: REFLECT

Reflection is the reset point in a side project. Every thirty days, you pause and evaluate
whether the direction you are exploring is still worth your time. The commitment is never
bigger than a month, which keeps the work light and the pressure low.

The purpose of the 30-day reflection cycle is to give you a clean way to continue, pivot, or
stop. Thirty days is enough time to make meaningful progress, but not so much that you
lose momentum if it turns out to be the wrong path.

You lose nothing by changing direction. You gain the clarity that comes from real learning.
Each 30-day cycle helps you narrow your focus until the path in front of you becomes
sharper, more engaging, and more exciting.

Here are five areas to guide your monthly check-in.

1. Enjoyment – Am I still having fun doing this work? Does this exploration feel energizing or does it feel like a chore?
2. Curiosity – Did anything I learned this month make me want to go deeper? Or has my interest in this topic started to fade?
3. Learning – What meaningful thing did I learn this month? Did anything surprise me or challenge what I assumed going in?
4. Direction – Is there something else I would rather explore right now? Has a new problem, industry, customer, or technology started pulling my attention more strongly?
5. Commitment – Does this direction feel worth another thirty days? Do I want to continue, pivot, or stop and choose something new?
   
   

These questions are simple, but they create a powerful feedback loop. When you reflect
consistently, you drop the paths that no longer interest you and lean into the ones that
hold your attention. Over time, the target shrinks. What began as a wide search becomes
a focused line of sight. Eventually, you find yourself staring at a bullseye: an opportunity
that feels exciting, aligned, and worth pursuing.

Reflection is what keeps the whole system working. It keeps you honest about what
matters to you and where your energy really is. And when you use this monthly rhythm to
guide your next step, you give yourself the best chance to discover the path that truly fits.

NOW THE JOURNEY BEGINS

The four steps provide a simple structure for running a side project and exploring what
might be possible. Focus, commit, explore, and reflect create a rhythm that moves you
forward without pressure and helps you learn in a way that thinking alone never will.
With this foundation in place, you can start building real momentum. The rest of this
guide will help you strengthen that process by showing you how to work with a partner,
how to think about investments during exploration, and how to get unstuck when
you›re unsure about what to explore. These tools make the journey easier and increase
the odds that your exploration leads you to an opportunity that truly fits.

PARTNERING UP

A side project becomes even more powerful when you explore it with someone else.
This is the approach my friend and mentor TA prefers, and it is how many of his best
ideas and collaborations have taken shape. Working with a partner does not change
the four steps of a side project, but it does introduce a few nuances that can make the
process more structured, more fun, and more productive.

When two people explore the same focus together, the experience becomes richer. You
each bring different perspectives, skills, and instincts. You notice different things in
your field trips. You ask different questions in interviews. You interpret your research
differently. And when you run small experiments, you often come back with different
insights. Put together, you learn far faster than you could on your own.

A partner also makes the work more enjoyable. Instead of exploring in isolation, you
share the discoveries, surprises, and challenges with someone who cares about the
same topic. That sense of shared curiosity is motivating, and for many people, it is the
difference between starting strong and staying consistent. The work feels less like an
obligation and more like a weekly adventure.

Bringing a partner into a side project does require a bit more structure, especially in
how you use your 20 percent planning time. TA likes to meet his partner for coffee
once a week. They sit down, share what they learned from the past week, compare
observations, and plan what each of them will explore next. These conversations create
accountability, sharpen insights, and keep both partners pointed in the same direction.
They also help prevent drift, which can happen when two people are exploring loosely
without alignment.

PARTNERSHIP

Partnership also changes the reflection process in small but important ways. In
addition to the five solo questions, you add a few more. Do we still enjoy working
together? Are we getting value from these weekly conversations? Are our strengths
complementary, or are we stepping on each other’s toes? Do we want to spend
another thirty days exploring this focus together? These questions help you evaluate
not only the project, but the partnership itself. Because if you enjoy the person but
not the project, you can change the focus. If the project is fun but the partnership is
not working, you can part ways without any cost or consequence.

This is one of the hidden benefits of partnering: it gives you a low-pressure way to
test what it is like to work with someone before you ever consider building or buying
a business together. You learn whether they follow through, whether your strengths
fit together, how they handle uncertainty, and how the dynamic feels. Many great
companies start with two founders, and a side project is a safe way to discover
whether you have the kind of working relationship that could support something
bigger.

Partnering is not required and exploring solo works perfectly well. But if you enjoy
collaboration, want to learn faster, or want to see how you work with someone in a
low-stakes environment, partnering up can make your side project more enjoyable,
more effective, and more revealing.

CASH BOUNDARIES

A side project is designed to be a low-pressure way to explore business ownership,
and that includes keeping your financial investment small. The goal of this phase is
learning, not building. Cash should support your learning, not drive your decisions or
create stress. A simple rule of thumb is that any money you spend should feel more
like paying for a class than making an investment.

Small, intentional costs can be helpful. Buying a book, attending a local event, paying
for a tool, or running a tiny prototype can all accelerate your learning. The key is to
decide up front how much you are willing to spend and to treat that number as a
boundary. It should be low enough that there is no stress attached to it. If losing the
money would bother you, or if you feel pressure to “get a return,” the amount is too
high for this stage.

CASH BOUNDARIES

The real purpose of a cash boundary is to protect you from getting ahead of your
learning. When you have a small budget, it forces you to break your ideas into
inexpensive tests. You have to de-scope your assumptions, simplify your prototypes,
and look for the cheapest way to answer the question in front of you. That constraint
is healthy. It keeps you from pouring money into an idea you might be excited about
but have not yet validated. It also helps you stay honest. The smaller the spend, the
easier it is to stop, pivot, or reset when the learning points in a different direction.

Cash boundaries also reinforce what a side project is and is not. This is not the time to
buy equipment, secure space, hire people, or invest in branding or marketing. Those
steps belong much later, after you have conviction and evidence. For now, think of
money as fuel for insight, not as fuel for building something.

A simple approach works well. Decide the small amount you are willing to spend in
a month. Decide the small amount you are willing to spend in total. Then let those
constraints guide how creative you get in testing what you believe. Good learning
does not require big spending. In most cases, it is the opposite. Small budget
constraints keep you focused on the most important questions and prevent you from
drifting into commitments you are not ready for.

A cash boundary keeps your side project light, flexible, and safe. Paired with your
time investment, it gives you the room to explore freely without putting anything
meaningful at risk.

THE MAGAZINE RACK TEST

Sometimes the hardest part of a side project is choosing what to explore. You may feel
the pull toward business ownership but not know where to begin. When that happens,
a simple exercise called the Magazine Rack Test can help you uncover the topics,
industries, or ideas that naturally draw your attention.

Picture yourself walking into a large bookstore. You pass a magazine rack filled with
every topic imaginable: health, home services, travel, finance, technology, wellness,
construction, design, fitness, food, education, parenting, real estate, and everything in
between. You are not thinking about business ideas. You are just noticing where you
drift.

THE MAGAZINE RACK TEST

Which section do you walk toward without thinking? What do you pick up first? What
do you flip through longest? What would you buy if you had to choose one?

You are not looking for a business concept on those pages. You are looking for a signal
of genuine interest. Curiosity is the fuel of a side project. If you choose a focus that
does not interest you at a basic human level, you will struggle to stay engaged through
the slow and sometimes messy learning that exploration requires.

If the magazine rack test sparks a few options, write them down and run them
through your PICT Focus lens. Is there a problem in that space you are drawn to
understand? An industry you want to look behind the scenes of? A customer group
you feel connected to? A technology you want to learn more deeply? The answers do
not need to be perfect. They just need to be interesting enough for you to spend a few
focused weeks exploring.

If you do not feel a strong pull toward any magazine, that is useful information too. It
means you may need to spend more time noticing what fascinates you in everyday life.
The videos you watch. The conversations you linger in. The articles you finish all the
way through. Most people’s curiosity shows up long before their awareness of it does.
The magazine rack test is not meant to give you the “right” answer. It is meant to help
you get moving when you feel stuck. It helps you choose a focus you will actually enjoy
exploring, and that enjoyment is often what keeps you committed long enough to
discover the opportunities that fit you best.

WHAT SUCCESS LOOKS LIKE

Not every side project will turn into a business. Most will not. But each one gives you
information you did not have before. You learn what types of work energize you, which
people you enjoy exploring with, and where your skills create the most value. You start
noticing patterns. Industries that feel natural to you. Problems that keep pulling you
back. Customers or technologies that spark your curiosity. These signals matter. They are
the breadcrumbs that help you narrow your focus and understand what might be worth
pursuing more seriously.

This is how conviction builds. Not through a single leap of faith, but through repeated
cycles of curiosity, learning, and reflection. Each 30-day cycle sharpens your
understanding a little more. Each exploration gives you a clearer sense of what fits and
what does not. Over time, the target shrinks until you are staring at an opportunity that
feels exciting, aligned, and achievable.

You do not need to go all in to begin. You just need to begin in a way that is consistent,
intentional, and safe enough to learn. Every side project is a small bet on your future self.
The goal is not to find the perfect business right away. The goal is to discover the kinds
of opportunities, environments, and work that bring out the owner you are meant to
become.