The Maker’s Dilemma

My story about the big decision every founder & freelancer inevitably faces, whilst navigating their pathless path.

Jonny Miller
Sep 20 · 7 min read

💌 Part I: An Unexpected Offer

Last week I received an unexpected call from a friend back in London. The unexpected catch-up call ended with an even more unexpected job offer.

I put the phone down not knowing quite what had happened. It was a doozy of a role:Chief Joy & Wellbeing Officer’.

Who wouldn’t want to add ‘Chief Joy & Wellbeing Officer’ to their bio—let alone at a well-funded startup whose values, team and mission was aligned with my own.

I put down the phone filled with ideas and intrigue.

The work itself would be fascinating too: designing meditations, facilitating a learning journey and contributing to an innovative learning curriculum.

So why wasn’t this a no-brainer?

Well, I’ve spent most of the year in exploration mode—which might be more aptly described as enthusiastic flailing. Or living life in ‘Gromit mode’…

I’ve had some ongoing freelance gigs (but still spending more than I’m currently earning) and have only recently begun to feel some real momentum on my side projects: publishers emailing out of the blue regarding a potential book idea, feeling immense joy after recording smile-inducing podcast conversations and positive initial feedback for an online course idea teaching meditation and breathwork to remote workers.

However besides the newsletter, none of these are generating revenue, let alone paying rent (which here in Canggu is far cheaper than London).

Yet I feel like I’m learning and growing every day, immersed in a wonderful community and realising that I might have something to share with the world.

So what was it to be? Back to London for a dreamy full time role or keep hacking through the unknown wilderness of side-projects here in Bali?


😬 Part II: The Decision-Making Process

There’s nothing quite like an incredibly tempting job offer on the other side of the world to dredge up questions what you really want out of life.

I consider myself relatively self-aware, but the funny thing about self-awareness is that you don’t know what you don’t know. Pages of journaling ensued:

Who do I most want to spend time with? What are the areas in my life that I’m looking to grow? What are the physical places and environments that I thrive in? What is the work that really lights me up? Are the creative rewards of riding freelancing and maker worth riding the uncertainty rollercoaster?

There is a wonderful irony to this in that I’ve run workshops on decision making in the past. I’ve hoarded decision making frameworks—everything from Jeff Bezos’ ‘Regret Minimisation’ formula, contributing to a friend ’s crowdsourced ‘Big Decision Spreadsheet, walking through ’s ‘anti-fragile planning’ essay, Tim Ferriss famous ‘Fear Setting’ exercise and more intuitive based approaches: recording my own ‘future-self’ guided meditations, reading ’s Should vs. Must… and at one point plotting my possible project ideas against what I considered to be my personal values.

side note: my friend adapted this and created a great template

Heck I’ve coached and mentored over 200 early stage founders and makers in a similar position of polarity–agonising over whether to make the leap to go full time on their side-hustle, whether to seek investment or perhaps most challenging of all: whether to throw in the towel on something that just isn’t working out.

The point however is this; and for fun let’s call it ‘The Bystanders Principle’: it is infinitely easier to advise someone else, than it is to navigate the territory when you are deeply emotionally invested in the outcome and experiencing tugs of inner conflict.


💡 Part III: A Decision Emerges

All frameworks aside, I found the most helpful thing was having friends kindly holding space to listen and reflect back my thought-processes and pick up on the underlying feeling tone of what I was saying.

After walking myself through many of the helpful frameworks above, it was an unexpected question from my housemate that brought clarity, here’s what she asked:

“Imagine feeling into a space of abundance, you have all of the time, resources and credibility that you need, forget all scarcity: where do you see yourself and what would you be working on?”

I sat upright and felt into this space. As if dropping her question into a well and being alive to what surfaced. And sure enough, moments later, it was as if the decision made me.

I experienced a visceral, felt sense of realisation in my chest and stomach as a goosebump-inducing wave of knowingness.

It was a sense that this was the place and community that I felt most at home. And a remembering that the Curious Humans projects are what have been fuelling my creative energy, my medium to share whatever gifts I possess with the world.

We both laughed. I found it fascinating that it was almost as if the decision needed to make its way down from my head into my body. I felt physically lighter.

This also enabled me to realise that some of the appeal of the role (despite being a wonderfully enticing offer) was that it would give me a get out of jail free card. A chance for both a regular pay-cheque and rapids-of-uncertainty life raft—a clear route deviating from the pathless path that I’ve been wandering along.

In other words accepting the role would have quelled the quiet voices of fear but at the expense of spending time and energy on the work that I feel called to create.

Here’s the email I eventually managed to summon the courage to hit send on.


📝 Part IV: Insights from Other Side

#1: Beyond Right & Wrong: It’s all an unfolding curriculum of life 👨‍🎓

I allowed myself to zoom the lens out a bit and appreciate that a former version of myself would have agonised over this, believing that my happiness and joy was contingent on choosing the ‘correct framework’ to make the ‘right’ decision. But with some guidance, I was able to look beyond the narrowness of this approach and rather view it as an opportunity for self-awareness, knowing that I would feel fortunate, fulfilled and content whichever direction I leaned towards. That in itself is immensely liberating.

#2: More Structure = Creative Constraints 📆

Although I feel like I’m in a good place right now, with good routines and supporting friends—the fact that I spent so much mental energy deliberating over this, revealed that there are some strong desires not being met — parts of myself out of alignment and seeking more structure, more creative constraints, more of focused mission, more surrounded by supportive humans to bring out the best from me. And if that’s not too much to ask, some clarity would be nice. Oh man, do I crave that sweet nectar of clarity.

#3 A Pledge to Future Me 📝

I’m not writing these words for your readerly pleasure. Oh no, this post is a purely selfish endeavour designed to make present me accountable to future me 6 months in the future. Because I know that by hitting publish on this post, if in 6 months time I have very little to show for my efforts — I’m no closer to launching either the Curious Leaders Academy, How to Human book or Deep Work Bootcamp and have instead simply churned through remaining savings, and someone sends me this post—then I’ll feel like the giant muppet who should have said yes to the doozy of a job offer.

#4 Deep Gratitude 🙏

I’d like to acknowledge the enormous privilege of being a 30-year old white male, without a mortgage, debt or a family to support. And even with that in mind, isn’t it amusing how quickly we humans can quickly lose sight of how absurdly fortunate we are, or give ourselves reasons to think that, if only I have this thing, that job or [insert anything in the external world] then we’ll feel really good. For me, it’s a never-ending cycle of remembering, forgetting, remembering again… that the real we feel in life joy comes from forging deep connections, knowing that we are innately enough and sharing our gifts with the world (and also that it’s okay to forget that every once in a while too!)


🤔 Parting Question

So my question for you indie makers, aspiring founders and floundering freelancers is the same one my housemate posed to me:

Imagine feeling into a space of abundance, you have all of the time, resources and credibility that you need, forget all scarcity: where do you see yourself and what would you be working on?

And if you don’t have any dilemmas of your own right now, imagine how you would respond if a hypothetical dream role appeared tomorrow. Would you take it? What questions of your own might this surface? Or what might it change about your approach and appreciation for what you already have?


💌 Enjoyed this story? Join the 950-strong League of Curious Humans and signup for my monthly newsletter

(And yes, you have full permission to abuse and troll me if I don’t follow through in the coming months)


🎙️ If you’re into podcasts you might appreciate this recent conversation with productivity polymath Tiago Forte.

👏 If this story resonated, do give it some love and share with a fellow freelancer or founder who you think might appreciate it.

Jonny Miller

Written by

Tribe Leader @Escthecity, growth @Litographs & cofounder @Maptia. Cold water surfer and ukulele enthusiast in my spare time!

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