Forget About Ideal, Get Real

Most Timeless Leaders Will Take a Portfolio Approach and Leave Glory Behind

If leadership is about lasting change, then we’re in trouble - all the leadership models out there that are dedicated to lasting change seem to count on a leader having all-in energy for a singular mission. For many reasons, the average leader - you and I, and most of the people we know – are unable or unwilling to martyr ourselves to just one cause and organization. Beating time therefore takes a different approach.

Welcome to Timeless Leadership! This week I finally share a working model for how I’m thinking about the Timeless Leader. I make connections back to some of the experiences detailed on this Substack since November, and comment on how I’m currently thinking this model can be practically useful for real leaders.

This model is a work in progress that I’m honored to share with you - we’re at the beginning of a ten year journey! I hope you find today’s piece thought-provoking. I’m genuinely excited to hear what it brings up for you and where you think we can go next.

Also in this issue:

• The upcoming Interlude

• $100 for 100 subscribers

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What is Timeless Leadership?

You know what I haven’t done in three months of writing this newsletter?

I still haven’t defined leadership.

If we were all together in a room right now, this would be the moment that I’d ask you all “what is leadership?” and start writing on a whiteboard. We’d probably get things like:

• Inspiring others

• Setting vision and direction

• Enabling action

• Fostering team cohesion

• Role modeling behavior

• Being the first to go

• Making the decision

• Persevering

• Making a difference

All these would be accurate, and you could probably add more to the list.

For the purposes of this discussion, let’s simplify it to two things:

1. Leaders have followers.

2. Leaders create change.

And it’s probably worth throwing out one qualifier:

3. GOOD leaders create POSITIVE, LASTING change.

If you’re in the business of leadership - either literally, you do it as a job, or spiritually, you do it as a calling - then you’re reading these words now because you know something is true:

Being a good leader is hard.

Especially solving for that “lasting” part.

An Idealized Version of Leadership

Let’s start with a simple framework to explore the three simple areas where a leader operates.

1. A leader leads themselves (they are their own follower)

2. A leader leads within an organization (a family, a team, or an institution with clear definition).

3. A leader leads a “movement” of people (not confined to organizational boundaries)

In an ideal world a leader has perfectly aligned interests and leads all three at the same time.

What leadership perfection looks like - leading everyone, all at once.

This is not rocket science. It’s a similar model (and has been influenced by) Stanford GSB’s motto “Change Lives, Change Organizations, Change the World,” The Leadership Consortium’s Leading “Self, Teams, and Business” framework, Box’s 4 Leader Mindsets, and my friend Nell’s “Me, We, World.”

There are two things to call out specifically about this representation that are helpful for where we’re going:

1. Orgs depend on leaders (you), and movements depend on orgs

2. A leader has different forms of authority at each level

Now, here’s the issue that I’ve been gradually poking at every week since November.

Notice the model above has three concentric circles. This representation represents perfect alignment among the levels. It visualizes the story of transformational leadership we’ve come to know and practically worship from our most storied leaders, including religious icons, political revolutionaries, and titan of industry.

When a leader becomes synonymous with a movement, they’re typically at the helm of an organization or group of organizations that is powering the movement.

All energy can flow in one direction.

Keep it going for many years, and you will change the world.

This is awesome, and truly works for some Timeless Leaders - the ones with monuments and national holidays.

But if you try this model (by founding a venture, or fully committing to an existing institution), you quickly realize how hard it is (I commented on my own entrepreneurial journey in a few posts, especially Jan 23rd). Your mission might be hard to monetize, or it might be hard to compete. You might realize you don’t care enough about the venture to commit your whole life to it, because you don't want to work constantly or you’re not sure it will even work, or you have more than one interest… OR you realize that the role you play in the organization doesn’t fit your skills or give you enough personal satisfaction, and you start to pine for something else.

By choice or by circumstances, few of us ever achieve full alignment, and if we do, it’s very brief.

Instead we’re leading with a very different, more complex arrangement with the organizations and movements we’re involved with… and the reality means we have much less time to ever achieve something timeless.

The 3 Time Sucks

Let’s start with your role in your organization. First, you’re generally not at the center of your organization, and you may not even be in a formal leadership role. By not holding the power in the organization, you have friction in working to gain followers and enact change.

You’re rarely the center of your organization.

When you’re not the boss, enacting change takes more time. This cost, combined with lower compensation, presents the first challenge to your long-term commitment.  

You almost certainly aren’t fully committed – you’re a human with a life outside of work!

Among your interests, my dear human, probably exists some movement you care about. If you’re like most people, there’s some cultural or political mission you believe in even more than the mission of your primary employer. For any number of reasons (usually financial) you don’t work full time on that problem… you have a job elsewhere to pay the bills.

When your job isn’t creating the change you care about most.

Ok, so now you’re straddling two priorities with minimal overlap. But that oversimplifies for most leaders… you’re likely involved in, or at least interested in, multiple movements for change.

When you DEFINITELY don’t have enough time.

Starting to see a pattern? When you’re pulled in different directions, you care about different movements, and maybe even contribute to different orgs that may or not be fully aligned to your vision for the movement, it’s difficult to find the time to lead any of them effectively.

You might try to cut back on sleep or meal times, but that’s not the solution.

Meanwhile, there’s one more thing.

Unless you have complete control over an organization, there’s no guarantee that you can stay on there forever. Probably you wouldn’t even if you could.

Oops, I guess we’re not leading THERE anymore!

Over time, your status related to various organizations and movements inevitably changes. You leave a job or lose interest in a movement (something I went through last year). Your leadership in those areas wanes or goes away altogether. When you then ramp up in something new, you’re restarting your journey, building fresh followership, working from behind to make positive, lasting change. All this takes extra time… time you probably don’t have.

To summarize, as a Timeless Leader you want to create something positive and lasting, but you don’t have time because:

1. You’re not fully committed to or in control of your org or movement. 

2. At any given time, you’re spread across multiple orgs and movements.

3. As time goes on, where you spend your time shifts causing disruptions and redirections.

It’s messy, but it’s real.

So what to do about it?

How to Save, Make, and Escape Time

Your goal as a leader is to create positive, lasting change. You have two options for how to approach time.

Option 1: Strive for “ideal” alignment

This is the most intense option that has been adopted by many visionary leaders. Most fail. A few make history.

You fully commit to one organization and the movement it’s all about. You streamline everything in your life around this mission. All your time goes towards it, you generate momentum, and this intensity and focus accelerates your time to impact.

The closest thing I ever did that looked like this was teaching. My discontent with the school system ultimately led me to rethink if I wanted to align to schools as my organizational home base, or look somewhere else.

In the “Ideal” Timeless Leader strategy, there is no Plan B. There are no guarantees. But it is a way to solve for time to create lasting change. (If this is your path, we should talk - I want to know how you got here, and how it’s going)

Sound a little scary, or downright impossible?

Here’s the alternative.

⭐️ Option 2: Operate in the “real”

This is the way that I see leadership working for most real leaders, now and in the future. You don’t personally get written into the history books this way. You probably also don’t become fabulously rich or powerful.

It’s also still hard.

However, it’s practical. It’s effective. It’s sustainable. It’s also fun, it lifts other people up, and it lets you off the hook for leading everywhere you’re involved (yes, you too can be a follower!).

Where to start?

First, Save Time

Think about the organizations and organizations you’re involved with like a portfolio. Chances are, your portfolio has some investment sprawl.

So bring some curation and intention to your portfolio. Like I described in my Hell Yes Club reflection, find a way to pick fewer things to be involved in. You don’t need to narrow it to just one (that might be too narrow, for various reasons), but maybe aim for 3 or fewer simultaneous commitments.

The elimination or reduction of connections to organizations and movements you passively track and feel guilty about letting down saves you time that can be better used elsewhere.

Not every connection needs to be fully severed – there are ways to minimally support the work of others – but find a way to get comfortable saying no. Some concentration is critical for the next step.

This selection process - what you choose to stay connected to - is one of the critical ways that you can also ensure you drive towards positive change.

Let go of some of your commitments to free up time you need to lead, especially where there’s unique potential for positive and lasting change.

Step 2: Make Time

With your more focused set of commitments, commit yourself to sticking around longer and using this time intentionally. With a longer horizon, you have a better chance of figuring out a viable path to change, building a following that trusts you, and ultimately achieving a lasting, positive change.

I haven’t figured out a way to visualize this yet, so this is basically the same image as above, but the “you” is a little smaller as you get less busy in preparation for step 3 🤷‍♂️

Your job as leader once you have commitments is to craft how you and other use your time to fulfill them. You “make time” in the sense that you determine how time is spent for others. Like the “time wizards” I talked about last month, you design, craft, and optimize the calendar and the clock to achieve sustained intensity and organizational efficacy.

Importantly, when making time, be sure to include boundaries for yourself and others. This allows for sustaining multiple interests, and the time needed to learn and teach other – the final step.

Step 3: Escape Time

With the time you have saved and made in steps 1-2, now you have the chance to escape the limits of time by unlocking the contributions of others.

You can increase your influence (aka your ability to lead) when you effectively TEACH others.

There are two ways that this is an escape. First, when you enable others to do what needs to be done, you no longer are constrained by the boundaries of your own 24 hour day. You are only limited by the number of people you teach, how well you teach them, and how prepared they are to apply the teaching.

If leadership is creating lasting change through your followers, the engine that powers it is the ability to influence and empower others. When this happens, there’s almost no limit to what can be achieved – you escape many of the time-based laws that constrain you personally.

But there’s a bonus, second escape.

Teaching is an act of love and engagement. By stepping into teaching, it’s a unique portal into the experience of flow. The expansive craft of teaching, combined with the richness of it’s meaning, can improve your own experience of leading and provide a fountain of energy to fuel your ongoing commitment.

In a nutshell, teaching is not only an escape hatch for progress. It’s also an escape hatch for experience.

And it’s an unrivaled practice of leadership.

In Summary

We’ve spent the last three months exploring some of the formative experiences of my life that have led me to some realizations about leadership:

1. There’s never enough time to be a “good leader” in the typical, real-life scenario

2. We’re not usually fully committed to an org or movement. Instead, we typically have multiple interests, and our commitments change over time

3. The “ideal” scenario - where we fully align self, organization, and movement - is one way to create lasting change, but it’s high risk and high cost

4. A more sure-fire way to lead well is to Save Time (curation), Make Time (design), and Escape Time (teach)

If you can master these practices, you can become a Timeless Leader.

What are you already doing to be a Timeless Leader? What will you do next?

The Upcoming Interlude

So that’s a wrap on Season 1! You might be wondering – what comes next?

My plan for the next phase for this Substack is to mix up the format and voices for a bit. I’m still planning to post at least every other Tuesday, giving me a more time for work with some other Timeless Leaders on guest posts. I’d also like to pepper in a few reviews of some interesting books and/or products, applying the Timeless Leader lens.

I’ll also invite some of you to some 1-1 and small group discussions on the themes raised here. I’m excited to hear more from you!

Then, on June 1^st I’ll announce the topic and schedule for Season TWO of Timeless Leader, which I’d like to start in the summer or early fall – but it depends on what the topic is!

$100 for 100 Subscribers!

In the past week we surpassed 100 subscribers of this Substack! In celebration of this small milestone, next week I’ll announce a prize worth $100 to one subscriber who replies to this email (or comments on this page) with an answer to this question – what was your favorite part of Season 1, and why?

Just make sure to reply by next Monday at 5pm PT for me to put you in the drawing.

Thanks for reading til the end – I hope it didn’t take too much time. ;)

-Joe