Let me give it to you straight: I think every leader needs a side quest.
Not another business.
Not another full-time commitment.
Just something that is interesting enough to wake up the curious part of your brain.
Maybe it is learning how to play an instrument. Maybe it is researching local history, restoring an old car, writing a book, studying theology, building something with your hands, or following a question that has nothing to do with your current business.
The point is not to create another obligation.
The point is to remain alive to possibility.
Focus Is Valuable: Until It Becomes a Prison
We have been taught that focus is the highest virtue of leadership.
And it is.
Focus helps you:
- Protect your priorities
- Make better decisions
- Finish important work
- Say no to distractions
- Move your mission forward
But focus can become a prison when it leaves no room for curiosity.
Have you ever been so committed to productivity that you stopped asking questions?
Have you ever become so efficient at doing the work that you forgot to wonder whether there was a better way?
A report from Mercuri Urval and the Global Curiosity Institute describes curiosity as a leadership capability that supports better decision-making, collaboration, learning, and innovation.
That makes sense to me.
Curiosity is often where the next framework, connection, or breakthrough begins.
Focus moves the mission forward. Curiosity helps you see what the mission could become.
Two Leadership Extremes I Want to Avoid
I have met leaders who chase every shiny object.
They move from idea to idea without gaining traction. One week, they are launching a new offer. The next week, they are exploring a different market. After that, they are rebuilding their entire operating system.
They never stay with anything long enough to learn what it can teach them.
That kind of leader is constantly busy but rarely clear.
I have also met leaders who refuse to explore anything outside their lane.
They become incredibly productive.
They execute. They optimize. They hit deadlines. They keep the machine moving.
But somewhere along the way, they stop being curious.
Their work may remain efficient, but it becomes less imaginative. Their decisions become predictable. Their leadership gets narrower.
Neither looks like the kind of leader I want to become.
So I am learning to hold both things at once:
- A mission that deserves my focus
- Enough margin to explore what might strengthen that mission
That balance matters.
My Side Quests Often Look Like Rabbit Holes
I have learned that I am prone to rabbit holes and side quests.
I will start researching one topic and end up somewhere completely different.
A question about leadership might lead me into psychology. A conversation about business operations might send me into the history of an industry. A problem with communication might lead me to study how people learn, make decisions, or build trust.
From the outside, it probably looks like a huge distraction.
Sometimes it is.
I am not going to pretend every rabbit hole is productive. Most of them are not.
But to me, those side quests are often where the dots get connected.
I notice a pattern I would have missed if I stayed inside the narrow boundaries of my immediate responsibilities.
I find language for something I have been experiencing but could not explain.
I discover an idea that gives me a better way to support our clients, our team, or the leaders we work with.
That is one reason I have stopped treating curiosity as automatically irresponsible.
Not every detour is a mistake. Some detours reveal the road you actually needed.
Most Side Quests Will Not Materialize
Here is the part that may bother the productivity crowd:
Most of my side quests do not turn into anything.
They do not become businesses.
They do not become content.
They do not become frameworks, products, or measurable initiatives.
And that is okay.
A side quest does not have to justify itself immediately.
You do not have to turn every interest into an asset. You do not have to monetize every hobby. You do not have to extract a lesson from every hour of exploration.
Sometimes curiosity is valuable because it gives your brain a different landscape to walk through.
Think of it like cross-training.
A runner does not only run in a straight line at the same pace. Strength, mobility, and recovery support the main activity. They may not look directly connected, but they help the runner remain capable over time.
Your side quest can work the same way.
It gives your mind a different kind of movement.
It can help you:
- Refresh your attention
- See familiar problems differently
- Build new mental connections
- Recover from decision fatigue
- Stay open to learning
- Remember that you are more than your current role
The opportunity is real. The impact is real.
Every Once in a While, One Changes Everything
Every once in a while, a side quest changes how I think.
It shapes a framework.
It sparks a new idea.
It solves a problem I was not even trying to solve.
That is the unexpected gift.
You begin with no clear agenda. You follow your interest for a while. Then, weeks or months later, an idea from that exploration shows up in a leadership conversation or business decision.
Suddenly, two things that seemed unrelated start to make sense together.
This is why leaders need room to think at a high level.
If your entire day is consumed by email, scheduling, file management, follow-up, and small operational decisions, your brain may never have the chance to make those connections.
You may be physically present in your business but mentally trapped in the details.
That is the fog.
At Dream Support, we often talk about the value of creating more brain space. A Remote Executive Assistant can help manage the administrative work that keeps interrupting your attention: things like:
- Prioritizing your inbox
- Coordinating your calendar
- Organizing electronic files
- Managing project details
- Maintaining systems and processes
- Handling routine follow-up
This is not about avoiding responsibility.
It is about identifying the work that only you can do and creating the margin to do it well.
Sometimes that high-level work is strategic planning.
Sometimes it is solving a complex people problem.
And sometimes it is giving your mind enough room to follow an interesting question.
Pay Attention to the Season You Are In
I have stopped feeling guilty about side quests.
Instead, I have started paying attention to the season I am in.
Some seasons call for intense focus.
There may be a launch, a crisis, a major transition, or a responsibility that simply cannot be ignored. During those seasons, the right side quest may be rest. Or family. Or a walk without a podcast.
Other seasons leave enough margin to explore a little.
You may have a stable team, a clearer calendar, or a business that no longer requires you to personally touch every detail. That may be the right time to pursue a question, hobby, or creative project.
Wisdom is not found by eliminating every side quest.
Wisdom is found by knowing which ones to let go and which ones are worth pursuing.
Try asking yourself:
- Is this restoring my curiosity or creating another source of pressure?
- Am I exploring this because it genuinely interests me or because I am avoiding important work?
- Does this fit the season I am in?
- What would a healthy boundary around this side quest look like?
- What might this teach me: even if it never becomes anything?
You do not need to give every interest unlimited access to your time.
You do need to stop assuming that every minute must be optimized.
A Simple Way to Make Room for Your Side Quest
You do not need a dramatic life redesign.
Start small.
For the next 30 days, try this:
- Choose one side quest.
- Give it a clear container, such as 30 minutes once a week.
- Keep a running note of questions, discoveries, and connections.
- Do not require an immediate business result.
- Reassess at the end of the month.
Your side quest might be:
- ✅ Reading outside your industry
- ✅ Taking a creative class
- ✅ Learning a new software tool
- ✅ Studying a subject you have always wondered about
- ✅ Writing privately without publishing
- ✅ Exploring a community or conversation outside your normal circle
- ✅ Building something simply because you want to learn how
The guardrails matter.
A side quest should support your life and leadership, not quietly become another full-time job.
And if your administrative workload is consuming every available pocket of margin, pay attention to that, too. Dream Support’s Remote Executive Assistant services are designed to help busy leaders get their heads out of the fog and back into the bigger picture.
You do not need to wait until your brain space is completely gone. You can lead from abundance and vision by creating room before the pressure becomes unbearable.
The Three Things Every Leader Needs
I am beginning to think every leader needs three things:
- A mission that anchors them.
- A few projects that move the mission forward.
- At least one side quest that keeps them curious.
The mission gives you direction.
The projects give you momentum.
The side quest gives you perspective.
Remove the mission, and you drift.
Take on too many projects, and you become scattered.
Eliminate curiosity, and you may become productive without remaining fully alive to the work.
That is not the kind of leadership I want.
I want to stay focused without becoming rigid.
I want to stay ambitious without becoming consumed.
I want to keep doing the high-level work while leaving enough margin for new questions, unexpected connections, and ideas that may not have a clear purpose yet.
That margin is not wasted.
It may be where your next meaningful insight is waiting.
The opportunity is real. The impact is real.
So, what is your side quest these days?
And if you do not have one, what is one small question you would enjoy following?
Cheering you on, 🚀 Micah
For more on creating the brain space to lead well, read Brain Space and explore how a Remote Executive Assistant can help protect your attention for the work only you can do.