The Bootstrapped Founder - Bootstrapped Founder #120: Fear-Setting

Dear founder,

While I was working on answering questions for my upcoming Twitter audience-building course, I ran into this one:

"What if it doesn't work?"

While my immediate thoughts went to the random nature of eventual success and how only consistency will pave the way there, I soon arrived at a problem that lies much deeper than that.

For many creators, the thought of their project not working out is debilitating. Their fear of failing is so strong that it keeps them from even starting, and that turns the fear into a self-fulfilling prophecy: you miss all the shots you don't take.

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In my experience, one thing has reliably helped me out of mental blockades like that: the practice of fear-setting. And since I am recommending it quite often, I want to do this exercise for my own fears, right now, in public. I hope that you'll find it interesting and instructive.

I first ran into this concept by listening to Tim Ferriss' podcast. It's relatively simple to do: for each fear you have, you envision the worst and define your nightmare outcome. Once you define it and reflect on it, it loses its power — you're starting to think about how to salvage a situation like that. You'll find that even though it might be a painful experience, you'll come out of it encouraged and renewed.

Let's see if that's true for my fears, shall we?

After we sold our SaaS business back in 2019, a lot changed in my life. I became a writer, and we moved from Germany to Canada. This change introduced many new things to learn and unknown risks to my life.

The biggest one was my career shift from developer to a writer. Before my bootstrapping adventure, I had a stable job, a regular income, and clear priorities. Now, I am responsible for my own schedule, and no one is telling me what product I should be working on. And that uncertainty quickly translated into fear after I started writing.

One of my biggest fears is that no one cares about my writing. A voice in my head tells me that —even though my book sales are doing perfectly fine— one day, they might just stop. One day, the collective population of the small business community will decide that my books aren't worth reading. My nightmare scenario as a writer is not to be read.

So, I reflected on this. I sat in my discomfort and envisioned a life where my books —print, eBooks, and audiobooks— didn't sell. No more passive income.

I did some inventory with my personal finances. Passive income isn't the only income I have —I follow Daniel Vassallo's great Many-Small-Bets approach— and that means that I wouldn't be strapped for cash anytime soon. I occasionally (and I mean very rarely) do consulting, the opposite of passive income. Should I ever need to replace the book money, I would have to spend maybe twenty hours a month talking to people and helping them. I do that for free on Twitter anyway!

And even if consulting didn't work, I have another asset that generates some revenue: PermanentLink, my little SaaS project. I could go full-time on that and ramp up my sales outreach if I wanted to. I've been neglecting this a little because my creator journey has been so exciting, but if it ever died down, I have a fully functional SaaS —with paying customers— to go back to.

Fear-setting allows you to embellish the nightmare: what if PermanentLink would implode at the same time my book sales dropped off?

Well, I still am a developer. In fact, I am a developer that has written extensively about finding business ideas within communities. I could focus my time on embedding myself (even deeper) in the communities I am part of, discovering their critical problems, and building a business with and for them. Building another SaaS in any industry that I am part of is definitely possible. I personally have encountered —and noted down— plenty of interesting problems over the last few years. Any of them is worth examining for criticality.

And finally, if I didn't have the opportunity to be an embedded entrepreneur, I could return to being a salaried software engineer. I assume that plenty of folks out there could use a developer with decades of experience and a successful SaaS exit under their belt. I could ask on Twitter and likely be talking to a few founders I admire within minutes.

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Fear-setting is an exercise in seeing the bigger picture you are in right now, removing yourself from an in-the-trenches-view and teleporting you into a fictional situation. As you can see, it opened my eyes to the fact that I have been successfully diversifying the risk of any of my small bets failing. If one of them breaks away, I have several opportunities lined up to replace it.

But most of them depend on my existing audience on Twitter. I have painstakingly built a public reputation on that platform for years now, and that induces an equally horrifying thought.

What if my Twitter account gets blocked?

I know that I would have to do something exquisitely stupid for that to happen, but this exercise isn't about likelihoods. It's about worst-case scenarios. So, I imagined that overnight, Twitter decided to remove access to my account, and —for added horror— I wouldn't be able to use any support channels to get it back.

At this point, I'd value my Twitter audience to be a significant part of my net worth — if you can quantify relationships like that. Losing that would hurt immensely. I'd be cut off from thousands of my people.

But it would not be the end of the world because I am prepared. I know that platform risk exists, and I have taken steps to diversify my audience. I have a newsletter with over 5000 subscribers — you're one of them! I have a podcast with a significant amount of listeners. I even have solid audiences on ProductHunt and —ahem— LinkedIn.

If I had to rebuild or even relocate my audience, I would have many lists (and eager audience members) to help me rebuild.

Growing an email list is my insurance against de-platforming. Email is a platformless medium, and I make sure to export and backup my existing list at least once a month. In addition to my newsletter subscribers, I also have a list of all my Gumroad customers. If I ever need to reach my audience or my paying customers, I have a way.

And even in the scenario of having left Twitter, the podcast lives on. The blog and all my content is still there. My tweets are also safe. Why? Because every few months, I download a complete archive of my Twitter data from my account page. It might take some work to make use of them, but I have the data, right here with me and backed up in multiple locations.

Again, fear-setting show that the only thing I have to lose is the time I'd need to put into restoring these things. The nightmare scenario I initially envisioned was just an inconvenience — a very annoying one, certainly, but not the end of the world.

But that brings me to my final, most visceral fear. It's not about my work, but about the condition that makes it possible: having a roof over my head.

What if my house gets flooded? What if a rogue tornado crashes into our little town and takes me to a magical world of witches and talking scarecrows? Honestly, though, what if something happens to the very place from which I am writing this?

Let's go there. My house —me not included— is on its way to the land of Oz, and all I could salvage was my phone and my wallet. I'd be surrounded by a supportive family that would immediately offer me shelter. My financial investments would be safe, although I might need to update the digital copies of my important documents. I'd be able to get a new computer somewhere, I'd be able to restore a backup, and I'd be up and running again in a day or two. Even if our house wouldn't vanish but "just" see some major damage like the basement flooding or a leaky roof, we'd find a way around that. I can work from anyone's couch, and I don't even need wifi to write. Also, I could just not work for a few months, to begin with. That's why I have set up passive income streams, both from the book sales as well as from other financial investments.

This is still not a fun situation to be in. We had a prior basement flooding, and fortunately, we could evacuate all our things just in time.

But in the end, they are just things. Tech can be re-bought, furniture replaced. We're taking precautions storing our keepsakes in high and safe places, but ultimately, we would get through it. For my professional life, it would barely matter. From a personal perspective, this would hurt much more.

Reflecting on this worst-case scenario immediately gave me a few actionable items to ensure I'm protected if the worst were to happen.

And I'd try to judo this into a positive experience, anyhow. In the build-in-public spirit, I'd probably turn that into a project. Arvid is rebuilding his home office. Why not document and share that?

It's in those dark moments that we can shine brightest, and fear-setting allows me to imagine myself in that context. I can start planning for all eventualities, setting up systems to prevent them from happening, and softening the blow if push comes to shove.

Remember that this is an intentional activity, with a beginning and an end. You're not going to benefit from dwelling on your fears at all times. Fear-setting allows you to compact these thoughts and feelings into a time slot, and you will have to let them go after that.

This can be harder than you think. Once your brain is aware of a fear, it will remember it and try to work it out. That's why fear-setting shouldn't be interrupted — you need to come to terms with every single fear and anxiety you tackle during this process. You will need to envision the nightmare, sit in your discomfort, find all the good things about that situation, and leave the nightmare again. So please, do this exercise when you know you have the time to calmly and intentionally think about things. This is not a spontaneous life hack.

Fear-setting can be used for much more than your professional life. You can think about health topics, spiritual questions, partnerships, relationships, livelihoods, anything that comes to mind. The boring term for this might be some sort of "scenario-based risk analysis," but I think it's more than that. It's a tool that allows us to face our fears while still putting our animal mind —the one that only knows fight or flight— at ease.

Give it a try. You'll come out stronger on the other side.

Thank you for reading this week's edition of The Bootstrapped Founder.

If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.

You can find my book Zero to Sold at zerotosold.com and The Embedded Entrepreneur at embeddedentrepreneur.com.

If you want to help me share my thoughts and ideas with the world, please share this episode of the newsletter on Twitter or wherever you like, or reach out on Twitter at @arvidkahl.

See you next week!

Warm Regards from Ontario,

Arvid