The above image represents the sum total of the progress I made yesterday. It sure doesn’t look like much. It is a grid system for an upcoming widget feature I am working on for Widgetsmith. I’m almost embarrassed to post it as the collective effort for an entire day’s professional work, but that is ultimately the point of this post.

I always find coming back from the Christmas break (or any break for that matter) challenging. The regular routines of my working life are joyously disrupted, providing a welcome break and opportunity to re-charge. But when I now sit down at my computer and face the wide-open expanse of possible work endeavors, I rarely have a clear sense of where to start and how to get back into the swing of things.

I’ve faced this struggle hundreds of times over the years of my career and navigated it with varying degrees of success. Over those years, I’ve built up a variety of “tricks” to get me going again. These are little habits or rituals which help steer me towards any degree of productivity again.

The above screenshot is an example of what I call my “Accomplish One Thing” rule. On any day when I’m supposed to be working, I have developed the habit of looking back at my day and looking for at least one thing which I really accomplished that day (ideally something tangible or visible). I tend to think about this as I’m clearing up my desk, ready to return to home life. It really doesn’t matter how big or small that thing is, but there needs to be something which I can point to.

The real magic of this habit is how it helps me earlier in the day. If I know I’ll need to have something tangible to point to later on, I find I am much more inclined to choose meaningful, but manageable tasks on these early days back. Tasks which are useful but also scoped to not overwhelm or daunt me. Obviously, not all jobs which need doing are atomic enough to be accomplished in a day’s work, but usually I find that I can either break larger tasks into smaller pieces or structure the sequence of work to allow for some of these.

The goal here is not to make massive progress; it isn’t about getting back up to full speed again, going from 0 to 100 miles/hour in one swift step. It is about building up my working inertia again. Speed is useful, but inertia is powerful.

Inertia in my working life is the thing which I find most powerfully motivates and animates my progress. It gives you that sense of inevitability about accomplishing the outcome and desire each morning to keep the ball rolling. Inertia is what will get you through the inevitable slumps, disappointments, and mistakes later on in a project. So I want to get it accumulating as soon as I can.

So yesterday I built that grid; today I’ll tackle the next thing I can accomplish in this project, and who knows what will come on Monday. But I know from experience that if I can string together a few days of tangible progress, the future will sort itself out.

This past weekend I was fortunate to be a participant in the “Relay FM 10th Anniversary Extravaganza”, a live show in London celebrating Relay’s decade of podcasting. Relay is the home of Under the Radar. We didn’t quite join at the start but have been part of the network for nearly 9 of those 10 years.

This event got me thinking a lot about longevity, especially as it relates to starting and sustaining a business. While nothing in business is ever certain, I firmly believe that Myke and Stephen didn’t reach this anniversary by accident. They have been careful and deliberate in their approach to building Relay, maximizing the chances of its enduring over time.

I feel like there are two extremes when it comes to starting a business you can build it optimizing for fast growth or you can build it optimizing for sustainability.

In the fast case you are likely rapidly increasing your costs and spending your way to growth. The goal here is to increase your customer base as quickly as possible and use whatever means possible to accomplish that.

In the slower, more sustainable case you are instead being extremely conservative with your costs and growing only as fast as you can without overreaching beyond your stable base.

Having been a close observer of the way Relay has grown and developed over the last decade it was clear they took the sustainable approach. Adding shows and employees at a very measured, deliberate pace. Never getting ahead of themselves and as a result rarely putting themselves in a tenuous position.

It reminds me of the Dry Stone Walls you will often see while wandering in the north English countryside. These walls divide farmers pastures and criss-cross the terrain on hillsides often battered with awful conditions. Yet these walls endure because they were built to endure. The process of building one of these walls is slow and deliberate. Only being able to progress at a rate of maybe 2-3 meters per day, but their lifespans are measured in centuries as a result. Compare that to something like a wooden split rail fence which can be put up at a rate of hundreds of meters per day, but have a useful lifespan measured only in years.

There are no free lunches here. If your goal is to make something which will endure, which can stand up against the storms which will inevitably batter it, you need to start building it with that in mind.

This isn’t to say that the fast, unsustainable approach doesn’t have its place, but moreover it is vital to be deliberate about what you want and be clear eyed about what that will mean for your future prospects. But if you want to make something which will be around to celebrate its 10 year anniversary you’ll probably to build it with stone rather than wood.

In Steve Jobs’s 2005 Stanford Commencement Speech he famously concluded by quoting the back cover of the Whole Earth Catalogue’s final issue.

It was their farewell message as they signed off.

Stay hungry. Stay foolish.

And I’ve always wished that for myself. And now as you graduate to begin anew, I wish that for you.

Stay hungry. Stay foolish.

Early in my career when I heard that quote it hit me as a lovely bit of motivational speaking. Something to encourage you to “get out there and do some good work”. The kind of thing you often hear at commencement speeches. I heard it has a positive affirmation.

Now that I’m further along in my career (and life) it hits me very differently. Now I hear it as a word of warning, a cautionary admonition.

When you are early in your career the best path forward is typically to hungrily strive forward. Embracing every possible opportunity, maybe not with foolish abandon but with consistent, unrelenting determination. You have everything to gain, and nothing to lose.

That works well enough until you achieve some level of success. Success is wonderful and lovely, but it also brings with it obligation. Once you have achieved something worth holding on to, you now need to do the work to maintain it. Once you have had some success now you suddenly have less to gain, and something to lose.

I noticed this in my own mindset after I had my first successes. It became much more difficult to pursue new opportunities with the same determined vigor as I did in the early days. I now would filter my decisions and new pursuits through an analysis of how they could negatively impact my existing accomplishments. It now felt reckless to undertake every opportunity, to jump at every idea.

Rather than being “Hungry and Foolish” it was now the prudent course of action to instead be “Defensive and Skeptical”. To be incredibly circumspect of which opportunities are worth the risk. To take actions which provide stability and preserve what you already have. To become comfortable with slow, measured growth.

I have no idea if this is what Steve Jobs meant in his commencement speech. He could have simply meant it in the positive, motivational sense. But increasingly I wonder if he may have also meant it in the cautionary sense as well. He had certainly overseen tremendous success and undoubtedly had to wrestle with the tension between preserving what you have and gaining something new.

Where I have settled in my own work is to strive to keep some meaningful part of my mindset hungry and foolish. To continue to be open to new opportunities and eager to explore them. I don’t want to end up miserly defending what I have already achieved, I want a professional life still rich with tackling interesting problems. Though admittedly I am more thoughtful in this pursuit.

In doing so one of the weird paradoxes of life also starts to emerge. I start to see that the only way to truly defend what you have is through continuous action. That defensiveness and skepticism are actually more likely to lead to loss. That it is action, and sometimes bold action at that, which allows you to keep hold of whatever success you have. Inactivity is depletion.