How to Get Old

Every year it gets harder to avoid the fact that I’m likely in the second half of my life.

There was a time when it felt like every weekend was filled with 21st birthday parties. Then weddings. More recently, it’s been funerals.

I’m also noticing a cohort of people who are about my age slip into midlife crisis. Typically these are people who forgot to be young when they were actually young.

It’s tragic to watch somebody who built a career or started a business finally achieve escape velocity only to immediately try to stop time, or even rewind - a young person’s car, a young person’s lifestyle, a young person’s relationship (often at the expense of the relationships that have supported them on the ascent), etc.

It’s equally awkward to watch somebody who lived without responsibilities for too long suddenly realise that all their friends are now ten years (or more) younger than them. Meanwhile the people they used to know have moved on and have very different interests.

The important question that often goes unasked is: what are the things we can only do, have and be right now?

Be sad about the future not the past

One of the things we all have to accept as we get older is that our body starts to fail.

It could be our eyes (fonts need to be bigger), our ears (music needs to be louder) or our liver (nights out take much longer to recover from). Or, in my case recently, joints and tendons.¹

Confronting knee surgery in 2021, I was warned that I might not be able to run again. I enjoy running so that was a dark thought for me, but slightly less so than it might have been because I’d run a lot while I still could. If I couldn’t run anymore at least I could look back fondly rather than with regrets. I’d miss what I no longer had rather than what I never had. I’d be sad about the future rather than sad about the past.

This is a useful aspiration. But even once we know, it’s surprising how hard we have to work at putting it to practise.

As someone prolific once explained to me:

The secret to having an amazing project to talk about today is to also have five other projects that won’t come to fruition themselves for weeks or months or years.

Not many people can multitask like that. And it’s contradictory advice because the key to making any one of those projects successful is dedicated focus. The people who solve that riddle are the ones we read about in biographies.

All of us mere mortals can just ask two questions each day:

1. What do we need to finish today, because the opportunity might soon pass; and
2. What do we need to start today, because the time has finally come.

The depressing bit, and the reason these questions are so often so hard, is a double whammy: the things we need to finish often needed to be started a long time ago (the best time to plant a tree is 20 years ago) and the things we need to start won’t pay off for a long time (if ever) so they are easily deferred.

I wonder if advice like this is even harder to understand if you live in a city or in a place with a temperate climate. Maybe it’s easier in the countryside or closer to the poles, where the change of seasons are more explicit. The biblical advice about there being a time to plant seeds and a time to harvest (and a time to rest) is more obvious where failing to do those things in the right season means missing the window for another whole year.²

Make hay while the sun shines. Pick fruit when it falls.

We can only be each age once.

Growing pains

When we forecast future growth it’s easy to draw smooth lines that go up and to the right.

But that’s not how it ever happens, in practice.

We rarely anticipate the dips, perhaps because those bits have been airbrushed out of stories of successful startups we aspire to emulate.

On the other hand, when we manage teams, we don’t always prepare for growth that happens suddenly, in bursts.

I’ve learned from painful experience, there are several points where early-stage and high-growth teams typically break, when our existing ways of working are no longer suitable and so our teams need to either age appropriately or fall into dysfunction…

30 People

The first common breakpoint is when the team grows to ~30 people.

This is when we need a clear organisational structure for the first time, with reporting lines and job titles and budgets and performance reviews. Which is not to say that we didn’t have or need any of those things previously, but more that they seemed less important when the team was smaller and everybody was mostly on the same page and just doing whatever was needed everyday to keep things moving.

This is when, for the first time, we have people in the team we don’t talk with directly every week. It starts to get difficult to keep up with what everybody is working on without conscious effort. The ratio of signal-to-noise becomes a problem and we need to start to filter. Our calendars start to fill up with status meetings.

Critically, this is also when the decisions that were made, often unconsciously in the early-days, about team culture and ways of working together, start to become embedded, for better or for worse. If the team is a monoculture that becomes more-or-less impossible to change.

120 People

Then, later, things often break again when the team grows to ~120 people.

This is when it’s unlikely that everybody in the team knows everybody else by name. At this size we need several layers of management, which causes the team to fragment. This could be by function, or by location, or by tenure. It’s much more work to get the team in the same room, let alone on the same page.

This is when the job of managing becomes a drag for people who are more suited to early stages. There is less need for generalists and more need for specialists. It becomes harder to vet every new hire, so inevitably we have to start to deal with performance management, which is never fun.

This is also when we start to get real diversity of style. If we want to maintain a shared culture we have to really work at it rather than just assuming that everybody will pick it up by osmosis.

If the team grows very quickly then the gap between these two breakpoints can seem depressingly short.

In the room where it happened

Another growing pain is assuming that people know how to work together. When teams are small this usually comes naturally, especially if we’ve hired people who are similar to us. But as the team gets bigger these things can’t just be implicit. The trend towards distributed teams and remote work makes this even more important.

There are three layers:

Hardware layer

Firstly, does everybody in the team have the equipment they need. Do we have the physical network and bandwidth installed? Do we have sufficient WiFi in the locations where people need to work, so that they have a reliable connection?

Software layer

Secondly, do we have collaboration tools like Slack, Zoom and Teams that allow people to work remotely and communicate smoothly with each other even when they are not in the same physical location?

Cultural layer

Finally, do we have the habits and techniques in place to ensure that this network and these tools are used effectively? Have we agreed what kinds of communications are appropriate for each of the different types of tools we use - what should be sent via email, what should be shared via collaboration tools, what could be a pre-recorded video update, and when do we need people to be available for a video call, etc?

At the start of the first COVID-19 lockdown I was asked by a journalist how I thought the internet would cope with the sudden shift to having the majority of people working from home. I said I was confident in the hardware layer and pretty confident about the software layer, but I was anxious about the cultural layer. I noted that the roll out of high speed fibre connections to many places had been completed just in time. As somebody who had worked mostly remotely for 5+ years prior to the pandemic, I knew that the software already existed and was reliable. But my expectation was that everybody would need to quickly learn the etiquette and, at least initially, would exhaust themselves by replicating familiar offline ways of working using online tools (e.g. long video calls involving one person talking and everybody listening, which are painful enough when everybody is in the same office, and terrible when everybody is on video). That’s exactly what happened.

It’s good to think about collaboration challenges in layers. It helps us quickly identify where the actual constraints might be and narrow in on possible solutions. Getting one or two layers right isn’t enough. To have a team that works well together we need all three.

Skip?

I recommend an exercise to help navigate these breakpoints and growing pains, regardless of the current team size:

Imagine the organisation chart when the team is three times larger.

Draw it on a whiteboard.

Don’t worry about putting names in each box, or providing detailed job descriptions. Think about what different functions or roles will be required when the team is that size. To answer this we need to think about the business model that will sustain the team at that point. And also the funding that will be required to get there.

This exercise is a great way to tease out the unit of progress to discuss with potential investors.

Having watched many founders struggle with this, I know this seemingly trivial exercise is anything but simple.

For a team of five, it’s hard to imagine what another ten people might do. How will the current jobs split? Likewise for a team of 20 people, imagining the structure when there are 60 in total can be difficult. What sub-teams will form? Who will lead and manage, and how many people will report to each of them?

Two areas that are often overlooked are HR and Finance (this is the “company” machine). In a very small team these are jobs that everybody does, and so nobody does. But as the team grows they become separate functions, and are vital to fuelling the growth itself.

Another common point of tension is the split between product and marketing/sales, and within the product team the split between engineering and operations. Again, in a smaller team these are functions that are typically shared between multiple people where everybody does a bit of everything, but as the team grows these will become areas with assigned responsibilities and how those interact becomes critical.

After drawing the boxes we can start to think about the existing people we have in the team today and how they might fit into that future structure. Where are the gaps? Where do people need to evolve their role or start to specialise? Who will still be excited to be part of the team at that size and who will likely want to move on at that point?

Once we’re done, then do it again, but this time imagine the team when it is five times as big as it is now. This will highlight a whole new layer of complexity.

The good old days

A few years after Trade Me was sold, I bumped into somebody who joined the team shortly after I had left. I asked them how it was going. They complained that the culture was changing. The implication was that it was no longer as enjoyable to work there as it had been previously.

I couldn’t help but chuckle.

One of the mistakes we often make when thinking about startups is imagining them to have a steady state. It’s not that they one day change. It’s that they are constantly changing and continue to only ever change as they get bigger and more mature. Teams also only get to be each age once.

This can be invigorating but also exhausting.

Growing really fast isn’t a natural state for a company. And as a result it’s always fleeting.

Most things that grow really quickly are bad things - cancers, viruses, wildfires.

To keep fast growth under control and make it a positive experience requires careful curation and constant attention. It doesn’t just happen. We have to repeatedly break things to fix them. If we think a few moves ahead then we can adapt and get to the next level. Then to the one beyond that.

If we have the opportunity to work on something that’s growing fast, we need to appreciate it in the moment. It’s difficult, maybe impossible, to see it when we’re in the eye of the storm, but those are the good old days we’ll look back on and reminisce about.

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