The Lone Wolf’s Guide to Collaboration: A Practical Guide for People Who’d Really Rather Do It All Themselves
Let’s be honest: some of us aren’t born team players.
We care deeply about quality, speed, and getting things right, and we've learned to protect those values by doing things ourselves.
At some point, however, even the most focused lone wolf hits a limit. Our Great Work becomes too complex, too ambitious, or too meaningful to carry alone. Not because we're falling short, but because we're aiming higher.
Even the greats had collaborators—Steve Jobs, Beyoncé, Einstein. If we’re serious about doing work that matters, we need other people, too.
This guide walks you through seven common resistance points, accompanied by short video lessons and journal prompts, to help you convince yourself that collaboration is worthwhile.
You don’t have to love committees. You don’t have to like meetings. But you do have to stop doing it all by yourself.
Let’s begin.
Want to skip to your biggest area of resistance? Reasonable.
Here’s a table of contents:
Why You Shouldn’t Go It Alone
"Even the people we think of as lone wolves who make big contributions had collaborators sharpening, challenging, and supporting them. You won’t do your great work alone. It’s just not possible."
Before we delve into the practicalities of resistance, we have to ask: Why must we collaborate? Can’t we just go it alone?
You can. You know this because you have been! And believe me, I know how tempting it can be to shut the door and get ‘er done.
Unfortunately (or fortunately, depending on my mood), my experience has been that meaningful work that impacts the world (aka, Great Work) is bigger than any one person’s time, skill set, or perspective.
You may very well begin in solitude with a great idea, but your breakthroughs will come through conversation, challenge, and connection. This is the mindset shift that Chapter 7 of Great Work opens with.
Journal Prompt from The Lone Wolf’s Reflection Guide:
Think about a time when someone helped shape your work for the better.
What did they offer that you couldn’t have created on your own?
What changed as a result of letting them in?
👉 Want a printable version with all seven prompts and writing space included?
It’s Not Easier, It’s Smarter
"You’re not wrong. It’s not easier. It’s just (eventually) better."
Let’s tackle one of the most common lies we’re told: Delegation does NOT make things easier. As lone wolves, we often believe we’re already doing it the “easy” way by doing it ourselves. No meetings. No delays. No miscommunications.
But easier isn’t the goal.
Delegation is not about passing off busywork. It’s about working smarter, not harder, by freeing yourself to focus on what only you can do.
That’s the high-leverage, high-impact work that your Great Work actually demands.
Journal Prompt from The Lone Wolf’s Reflection Guide:
What do you currently spend time on that only sort of requires you?
Make a list of tasks that someone else could do with a bit of direction.
What could you make room for if those were off your plate?
Use the dot pages in the back of your Great Work Journal to explore how you might make that trade.
👉 Want a printable version with all seven prompts and writing space included?
But What About All That Drama?
"Collaboration doesn’t have to mean drama. It can mean clarity, trust, and powerful co-creation."
Collaboration doesn’t have to mean drama. It can mean clarity, trust, and powerful co-creation.
For many lone wolves, this is the heart of the issue:
We’re not afraid of hard work-we’re afraid of mess.
Slow progress, unclear expectations, clashing styles, and unspoken resentment. Drama.
But drama isn’t a feature of collaboration. It’s a symptom of poor boundaries, low trust, or unclear expectations. And it can be prevented. With practice, you can build collaborative relationships that are grounded, energizing, and drama-free.
Sounds like a lot of work? You’re right! But this is the moment— where the drama feels inevitable and collaboration feels too costly—where the transformation begins. As you develop the skills to set boundaries, choose partners wisely, and communicate clearly, you start to see what collaboration can actually offer: clarity, trust, and momentum.
Journal Prompt from The Lone Wolf’s Reflection Guide:
Think about a time when working with someone felt frustrating or draining.
What created the tension?
What would you do differently next time to create more clarity or safety?
👉 Want a printable version with all seven prompts and writing space included?
Just Because You Can Doesn’t Mean You Should
Letting go of work you know how to do well is hard. Especially when you’ve already invested the time to get good at it. That was me—I would figure out how to do it first, and then when it came time to delegate, I was already too far in. It felt wasteful to hand it off.
The only thing that helped me break out of that cycle was this: I had to hire someone who was objectively better than I was. That was the only way I could let go.
When I paid experts to participate in my Great Work, I watched as things I had merely mastered became extraordinary in their hands. What had been my “good enough” lived in their zone of genius—and it changed everything.
Journal Prompt from The Lone Wolf’s Reflection Guide:
What is something you’ve been holding onto because you know you can do it “right”?
What would it take to trust someone else to take it on?
How would it feel to have that space back?
👉 Want a printable version with all seven prompts and writing space included?
Ask for Help (Before You Think You’re Ready)
"We wait until we’ve got it mostly figured out. But if we ask earlier, we can move much faster."
Most lone wolves wait until the work is polished and nearly done before sharing it. We want to be sure. We want to avoid the sting of “Why are you doing it like that?” But that delay costs us valuable insight, momentum, and creative energy.
Asking for help early is not a risk—it’s a strategy. The sooner we invite feedback, the more time we have to integrate it while the work is still flexible. Early help makes everything better: the idea, the outcome, and the experience of bringing it to life.
Still feel uneasy? That’s normal. One way to make it safer is to lower the stakes. Write a draft request. Practice saying it out loud. Ask a trusted colleague to weigh in on how you’re asking before you actually ask.
Trust me: It’s worth it.
These early steps—asking for feedback before you're ready, practicing the ask, making space for someone else’s voice—are how we begin to shift from isolation to co-creation. They help build the confidence that will carry you into deeper, more rewarding collaboration.
Journal Prompt from The Lone Wolf’s Reflection Guide:
What’s something you’re currently waiting until it’s “ready” before you share it?
What’s one piece of early feedback you could ask for now?
Who can you invite to give you feedback?
Why not write a draft request right here, right now?
👉 Want a printable version with all seven prompts and writing space included?
Segment 6: Hire Experts, Not Just Helpers
"I already know how to do it—and I know how to do it well."
That’s the trap, isn’t it?
Lone wolves are highly competent. We get good at things quickly, and we pride ourselves on figuring it out. So when someone says, "You should hire this out," our resistence whisper: “Why pay someone when you can do it yourselfjust as well?”
Here’s are two hard truths:
Doing something well doesn’t mean it’s the best use of your energy.
“Well enough” is not the same as mastery. It took me a long time to learn that what I had taught myself to do out of necessity—book design, video editing, branding, web development—was someone else’s actual zone of genius.
When I finally started investing in experts, not just helpers, everything changed. I saw my work sharpen, my message clarify, and my capacity grow.
I didn’t just save time, I created more impact.
Hiring experts is a powerful way to honor your Great Work. It says: This is worth getting right. This is worth leveling up.
Journal Prompt from The Lone Wolf’s Reflection Guide:
What are you currently doing “well enough” that an expert could do brilliantly?
What would it take to trust someone in this part of your Great Work?
Who do you know who might be worth the extra money if it helped you learn to trust in collaboration?
👉 Want a printable version with all seven prompts and writing space included?
Segment 7: Becoming a Pack Wolf (Without Losing Yourself)
"You don’t have to become a totally different person to benefit from collaboration."
This final segment is about evolution. You can stay discerning and independent while also sharing your Great Work with others who will sharpen, strengthen, and scale it.
Many lone wolves imagine that collaboration means compromise—watering down your ideas, slowing down your pace, or dealing with the chaos of too many cooks in the kitchen. But the truth is, collaboration done well doesn't dilute your voice. It amplifies it. It helps you see what you couldn’t see alone, and create what you couldn’t create alone.
When you move from working solo to building shared momentum, everything starts to shift. You become more resilient. More creative. More willing to take risks because you're not carrying it all on your own.
Every step you take toward trusting others is a step toward unlocking the kind of Great Work you couldn’t reach on your own.
Use the collaboration spiral below to see where you are on the journey—from doing it all, to delegating, to co-creating, to innovating together. Every step forward is a choice to let your Great Work grow beyond you.
Journal Prompt from The Lone Wolf’s Reflection Guide:
Take a look at the spiral: where are you on the collaboration journey?
Are you still trying to do it all?
Are you starting to hand things off?
Are you shaping work with others in real time?
Or are you ready to build something you could never create alone?
👉 Want a printable version with all seven prompts and writing space included?
Download the Free Reflection Guide.
Final Thoughts: Lone Wolves Still Run, But They Don't Run Alone
You can be fiercely independent, highly capable, and allergic to mediocrity - and still need other people.
You can stay discerning about who you let in, how you work, and what you share - and still grow faster, go farther, and build braver things when you collaborate.
Your Great Work is too important to stay small. It deserves more input, more impact, more reach. And that means learning how to build a team, a partnership, a pack - even if it’s just one trusted collaborator at a time.
So what now?
This is the path Chapter 7 of Great Work lays out in full: how you gradually learn to trust, mitigate risk, and open your work to the insights, skills, and genius of others. Not all at once, but layer by layer. That’s where the real transformation happens.
If this guide stirred something in you, there are two places to go next:
Get the Journal Prompts as a Printable Guide
Reflect on your Great Work with more depth and clarity. This free PDF includes all seven journal prompts from the Lone Wolf’s Guide to Collaboration, plus space to write as you go.Read Chapter 7 of Great Work
It walks you through the full path from lone genius to collaborative innovator, with real-world stories and practical mindset shifts to guide your next move.
Collaboration might not make you fundamentally less of a lone wolf, but it will just make your Great Work bigger, stronger, and (when done well) a whole lot more fun.
You’ve got this. And you don’t have to do it alone!
