The Problem With "We've Tried This Before"

Startups move quickly. Lots of things are tried and tested. Often conclusions are drawn quickly based on the information available at the time. 

Sometimes at startups a new guy enters the room and wants to try stuff that’s already been tried before. As a co-founder of onefinestay, this could drive me crazy. “We’ve tried this before - it doesn’t work” I used to think, & often say. Sometimes I was right, & sometimes we tried again - & had a different result. 

This issue is particularly hard to reconcile. Often “we’ve tried this before” is wrapped up in ego - “if I tried it & it didn’t work, its not like this person will figure it out”. There’s also the desire to always be learning, to not waste time, not make the same mistake twice. 

Yet conditions are always changing. The people around the table are changing, and are always assimilating new information. Organizational priorities change. The market conditions change. Internal capabilities improve. Technology improves. 

We need to recognize that things are always changing. The previous lessons learned can’t be strictly applied to the present time - doing so is a version of fixed mindset. 

So I try to always stay aware of the faulty logic that can be behind “we’ve tried this before”. 

Top 5 Books / 2017

  1. The 100-Year Life: Living & Working in an Age of Longevity - our kids have a 50% chance of living to 105 at the same time that many historical sources of financial and emotional stability are vanishing - what are the implications for happiness, employment & society?
  2. The Agony & the Ecstasy - beautiful historical biography of Michelangelo. He was a true creator, pursuing his passion of sculpting marbles despite innumerable obstacles & irrational incentives.
  3. Principles: Life & Work - a phenomenal meditation on self-care and org leadership, & a guidebook for building lasting companies.
  4. Homo Deus: A Brief History of Tomorrow - a darker companion piece to the also great Sapiens & 100-Year Life. How will many of us find meaning when routinized work is automated in the next 30 years?
  5. One Hundred Years of Solitude - in the 'post internet' world, where any question or image can be answered or discovered in seconds, creating a sense of true wonder can be hard. But as parents, & leaders, this is what we should be shooting for.

Leading from the middle

At a breakfast yesterday hosted by Bleeker, we had an in-depth discussion about leadership, & how to lead others. 

Leadership is a word that means different things to different people. We went around the room and no two people had the same definition of leadership. 

At one point the discussion evolved into style metaphors - e.g. servant leadership, leading from the front, leading from the back. Someone said they prefer to 'lead from the middle'. It's the first time I've heard this metaphor, and it really resonated.

The essence of leadership isn't about, on one hand, making a lot of decisions that cascade down through the organization, top down. Nor is it only supporting the team 'from behind' & getting the most out of every individual. It's both of those things. Leadership emerges out of knowing when to lead from the front, and when to lead from the back. When to employ wartime tactics, and when there's enough relative peace to focus on process. Achieving the right balance at the right time - staying fully present to the exact time and place the organization finds itself in - is leadership. In order to recognize this, you need to be in the middle. 

The same is true for team management. A common scenario that founders or senior team members find themselves in: person x just joined the organization and needs a lot of support. How much guidance should I provide? Should I be directive or much more hands off? 

The answer of course is it depends. Specifically it depends on the unique qualities of the two individuals - the manager and the managed. And the core values of the organization, as well as the specific time and place within its evolution. There are no template answers. In light of this, knowing the right way to proceed is leading from the middle. 

This is the danger of personality assessment frameworks (Myers-Briggs, etc.). These frameworks tend to assume a static environment and static personalities. In my experience the real world is much more complex. As soon as a unique individual is reduced to a box of 16 (or whatever), there's too much temptation to oversimplify how its best to interact with that individual. There are about 7.5 billion boxes in the world today. The best a leader can do is stay fully present to the needs of the individual and organization at that time. As soon as decisions are made based non-context specific rules or frameworks, problems emerge. 

This means that our organizations exist in a state of unending change & complexity. Leading from the middle is the ability to keep in balance the needs of the organization at that specific time - which is always evolving - and the needs of the specific individuals within the organization - who, like the company, are also always evolving. 

The Higher Education Question

I enjoyed listening to Bill Kristol interviewing Peter Thiel on his podcast - both interviews are worth a listen. The first interview dates from 2014, around the time Zero to One was released.

Thiel has strongly held and well-publicized views on the value of higher education. The university experience is not dramatically different than it was two or three decades ago - it just costs 400% more than it did in 1980 (post inflation). The student debt curve is very steep and getting steeper:


At the same time, the nature of work is changing. Outside of a few elite programs, university is no longer the best option to learn about cutting-edge technologies that will drive the future of work. It certainly isn't the nimblest. And it's an increasingly expensive way to acquire essentially a generalist skill-set: significant re-education and retooling will be required to keep pace with change over the next 30-50 years.

I would also imagine that the value of a university degree from all but the most elite colleges is quickly eroding. Skills acquired from certification programs like the Flatiron School, cheap or free online courses, or self-education from the proliferation of content, can be immediately applied in a real world setting. ROI is nearly infinite and the cycle time is short. 

We don't know what the future of work will look like, but we know with a high degree of certainty that work will be very different. According to one estimate by two Oxford researchers, 47% of US jobs will not exist by 2033. 

David Perrell, The Future of Work

David Perrell, The Future of Work

It was one thing to invest time or money in a college education when the employment market was relatively static - the jobs were in military, agriculture, financial services. It's another thing entirely when many jobs we now do won't exist in 30 years, and the jobs we will do don't yet exist. 

This isn't to say a college degree is no longer worth it. For some it certainly is - but I don't think its such a no brainer anymore. The situation is stark enough to call into question on an individual basis whether a 4-year and six-figure expenditure will have the kind of ROI one would expect from an investment of this quantum. 

What other possibilities might exist for 4 years of time and (if you are fortunate enough) that kind of money?   

The Smartphone / Vacation Paradox

Today feels like the real start of the work year, back in the saddle after August. I spent two weeks on the west coast with my family - one week working in LA, and another week off in Las Vegas. 

Technology - specifically smartphones and wifi - has permanently altered vacations. Our habitual checking is hard to switch off when we go away for relatively short periods of time. It’s tempting to ‘unplug’ or take an extended ‘digital sabbath’ - however practically speaking smartphones are so ingrained in how we communicate with each other, this can end up a serious inconvenience. Try meeting up with extended family different hotels without text messaging - it can actually be inconsiderate to be unplugged! 

It’s tempting to vilify the iPhone and what its done to the modern family, nostalgically looking back at smartphone-less vacations. However, the same device provides unprecedented flexibility for where work can happen, which in turn can giving back us much more time with family & friends. Remote work has been normalized. Even if we don’t want it, our colleagues or stakeholders expect us to be available at short notice. 

So what’s the answer? On one extreme there’s the ‘airplane mode’ holiday - I see many people do these, although they don’t work for our family. And expecting to create real value as a growth company unplugging for multiple weeks a year isn’t realistic. 

On the other extreme, reflexive email creep can lead to your body on vacation while your brain is still at work. I’ve experienced starting a vacation week barely checking email, but by the end losing all discipline and falling back into normal checking patterns. 

I think we’re experiencing a paradigm in what it means to really be on vacation. Being conscious about this can lead to the biggest work-related lifestyle improvement in the past 100 years - the ability to work effectively, remotely, for far more time than the typical US worker currently takes off as vacation time. 

However we need common sense rules of thumb - its hard to imagine value created in a company where employees are at remote locations simply responding to each other for several weeks or months a year. And we need to shift our mind patterns - just because we can see the ocean or are deep in the mountains doesn’t mean the work stops. 

Remote work is here to stay. But work means proactive work - kicking off new initiatives, selling, driving results. I can imagine personally being effective for 2 months or more in this pattern. 

True vacation is something else. It’s reactive work. Whether this means its possible to unplug fully depends on many factors. Personally, I like to ensure value is building in my absence, which means responding to the occasional email or even ensuring a project stays in track. 

In true vacation mode the key lies in conscious choices. If I need to check email, I do so consciously rather than reflexively. I am making a choice. I also take a few breaths before checking, to ensure that I’m centered. I also try to not engage in debates that can turn emotional and therefore spill into my subconscious throughout the time away - I stick to the basics. 

I think solving the remote work / vacation / office time equation can allow us to live better lives, with more time experiencing and bonding with loved ones and friends. But if we’re not careful, we can sleepwalk into never really being on vacation, or potentially worse, work for companies where no real work is getting done.