Creative Wayfinding For Ambitious Optimists.

The Two Tipping Points Behind Every Breakthrough Success

May, 15, 2021

Back in 2015, I was a landscaper with dreams of traveling the world full-time.

I had recently discovered the wide world of podcasts and was able to listen to them at work. Naturally, I spent nine hours a day binging my way through every online business podcast I could find.

After a month or two of listening, I started experimenting with what I was learning. I built (ugly) websites, and dreamt up (bad) business ideas, all the while feeling (mostly) confident that eventually, I would land on something that would gain traction.

Despite my general optimism, however, there was a small shadow of doubt in the back of my mind. What If I never landed on something that gained traction?

Whenever it surfaced, I did my best to push the thought further back into the darkest corner of my mind.

Six months passed. The idea I was most confident in was a photography blog that had a small, readership of a hundred people or so. Eventually, I planned on creating online courses in order to generate income. I had no idea what I would teach, but at the rate the blog was growing that I wouldn’t need to make a decision for a long time.

I dreamed of reaching the tipping point. The day when my work would start to pay off and the results would pour in.

In my mind, the tipping point meant thousands of new page views and hundreds of new subscribers per month. But to be honest, I would have settled for any clear sign of traction at all. Any proof that what I was doing was working, and worth my continued investment in.

As it turns out, that proof was right around the corner, just not for my photography blog.

One day at work, I was listening to one of my favourite shows, Zero To Travel, when the host, Jason, mentioned his podcast editor in an offhand comment.

Now, I had considered podcast editing before, but my ego always kept me from taling it seriously. It felt like a waste of my skills, being the professionally trained sound engineer that I was.

Jason’s comment, however, struck something inside me in a way that resonated in a way it never had before. If my goal was to build a business that would allow me to travel, surely this was a quicker route than building an audience and creating courses.

That night, I created an UpWork profile and began scouring the site for podcast editor postings. I quickly discovered there was no shortage of people looking for editing support. Before the night was over, I had applied to them all.

Three days later, I had landed my first gig.

At $30 an episode, it wasn’t much. And yet, in landing that first client, something inside me shifted. I realized I had reached a tipping point–just not the one I had been envisioning.

I knew that if I could get one client, I could get another, and another, and another until I had enough clients to quit my job and book a plane ticket. I didn’t know how long that would take, but I knew I was now on a path where that outcome was not just possible, but inevitable.

With this realization, I learned an important lesson.

A Tale of Two Tipping Points

I know I’m not alone in waiting for the tipping point, that big break after which we can stop feeling like we’re pushing a boulder up a hill and we can start reaping the rewards of all the work we’ve put in without the continued effort.

Maybe the tipping point you imagine is a piece of content going viral, a major media feature, or your first 6-figure launch. Maybe it’s getting hired for your dream job.

Let’s call this the Tipping Point of Effort.

No matter how pragmatic an approach we might take on a day-to-day basis, I think we all harbour some fantasy about what our big break will look like and how life will be different once it arrives.

This tipping point is external and measured by tangible results. It’s marked by the point at which the same amount of effort begins to generate a greater and greater return. While it might feel like reaching this tipping point is the goal we’re ultimately working towards, it is not, in fact, the only tipping point. And it’s not the one that matters most.

Long before we arrive at the Tipping Point of Effort, we must first reach another. This other tipping point is the Tipping Point of Belief. This tipping point is internal. And while it might not be measurable, the difference it makes is significant.

The Tipping Point of Belief is the point at which we realize that we’re on to something that will work if we simply give it enough time. We likely won’t know how much time it will take to reach our end goal but we know that we’re on the right track. Once we’ve passed this tipping point we can be confident that we’ll get there as long as we keep moving forward.

This is what I experienced when I landed my first podcast editing client. I had landed my first client quickly, but I had no idea how long it would take to add the additional 5-10 clients to my roster that I would need to support myself.

I remember thinking that it might take a year or two, and I was ok with that. In fact, I was ecstatic. Once I’d passed the Tipping Point of Belief, the timeline didn’t really matter. I was happy to put in the work, no matter how long it took, knowing that in the end, it was going to get me to my goal of full-time travel.

Six months later, I had quit my job and was on a plane to Europe.

That’s the thing about reaching the internal tipping point. The work doesn’t get any easier once you’ve reached it, but the clarity and confidence that come with it make it feel like you’re now moving downhill. Overnight, you’re able to bring more focus to your work because you’re not second-guessing whether your time would be better spent elsewhere. It just so happens that another side-effect is taking more joy in your work as well.

This shift leads to better work, which builds momentum. This then speeds the arrival of the Tipping Point of Effort, where the results begin to compound.

Reaching the Tipping Point of Belief isn’t just about speeding up the process, however. It’s almost impossible to reach the Tipping Point of Effort without it.

This creates a problem for us as creators.

Most of us haven’t yet reached the Tipping Point of Belief. We don’t know for certain that we’re on the right track, and are constantly second-guessing our decisions about where we spend our time. If the Tipping Point of Belief is a necessary checkpoint on the way to the results we’re chasing, how do we get there?

How To Reach The Tipping Point of Belief

The first thing to understand is that getting past the Tipping Point of Belief doesn’t mean you’re free of doubt in every facet of your work. You’ll still face myriad choices about how to create, market, and sell the work you do on a regular basis. Without having reached the tipping point, many of these choices might feel paralyzing.

The difference, I think, is that once you have the belief that you’re on the right track, you realize that these choices don’t actually matter all that much. It’s clear to you that your decision to build your audience on Instagram or Twitter, Youtube or Podcast certainly won’t make or break your idea.

The Tipping Point of Belief is often (but not always) marked by some external validation. For me, this was landing my first podcast editing client. For that validation to mean anything, however, it has to be the result of a process.

Getting a client by fluke is little cause for belief. Getting a client as the result of a defined process, however, gives you the confidence that you can repeat the process and get the same result. Achieve this, and you know you’re on to something.

We all have different skills, traits, perspectives, and results we’re working towards. But there are three things that will help anyone get to the Tipping Point of Belief faster.

An Idea Generation Habit

The first is developing a habit of generating ideas. Not necessarily good ideas, but a lot of ideas.

Since the start of the year, I’ve added almost 1,000 ideas to my list of potential blog or newsletter topics. Of that list, I’ve only ended up writing about 83 of them.

Developing the habit of constantly generating new ideas opens up your eyes to just how much opportunity is out there. This allows you to then be much more selective about the ideas you do choose to pursue. It also gives you confidence in your ability to find solutions to the problems you’re likely to encounter in the future.

The thing that trips people up when trying to build a habit of idea generation is thinking that every idea needs to be a viable business or product. Most ideas won’t be.

What you’re looking for instead is the tiny seeds of ideas. Things that pique your curiosity, that you’d like to explore more, or little insights throughout your day.

The most effective way to kickstart this idea of noticing small ideas is to write every day. Even if it’s on Twitter or Instagram, make a commitment to share one post every day around an insight you’ve had. This commitment has a way of queuing your subconscious to keep an eye out for topics to write about. Pretty soon you’ll find yourself filling notebooks with ideas as you go about your day.

A Habit of Shipping Work

Tied closely to the idea generation habit is a habit of shipping work.

As mentioned above, the idea generation habit is most easily achieved when you’ve made a commitment to publish something–no matter how small–every day. That said, reaching the Tipping Point of Belief will likely require you to ship more ambitious projects than daily tweets.

Starting, shipping, and closing out a variety of projects helps you explore different mediums, offers, and strategies. Over time, you’ll discover which resonate most strongly with you and where your strengths and weaknesses lie.

The habit also builds confidence in your ability to make a plan, execute it, and achieve a result. When combined with an idea generation habit, and a clear direction, these two skills will make you unstoppable.

Trust & Commitment

The final requirement for reaching the Tipping Point of Belief is trust and commitment.

Reaching the tipping point is going to take time. It’s going to take having a lot of bad ideas and shipping a lot of bad work.

Trust in yourself and commitment to the process are essential to make it through this early stage when you’re most likely to be wracked with doubt and frustration.

The best way through is to keep creating, however. Keep generating new ideas, keep shipping, keep iterating, and keep trusting that eventually, the process will lead you to where you need to be.

A New Tipping Point

I’ve recently felt myself pass another Tipping Point of Belief.

The first time was marked by a single significant instance of external validation–getting my first client. This time around, the approach and transition has been more subtle.

In short, this tipping point has felt a lot more like… well, a tipping point. A slow, steady build-up of a body of work suddenly giving way to something greater. The hundreds of blog posts and newsletters I’ve written over the past year and a half beginning to organize themselves into a larger whole.

My goal, for a while has been making a living as a full-time creator. Over the past few weeks, I’ve felt that goal shift from possibility to inevitability.

I’m still foggy on many of the details, but I feel the critical mass of ideas steadily coalescing into a more clearly-defined vision.

As with last time, I don’t know how long it will take to reach the goal. Six months? One year? Two? At this point, it doesn’t much matter. It will take however long it takes, and I’m certain that as long as I stick to the process, it’s only a matter of time.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.


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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

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