The Second Season:

The quiet disconnect founders find on the other side of success.

TRANSCRIPT:

There’s a particular moment in the life of a business that I don’t think we talk about anywhere near enough. Some of you know it well - it’s not your first season as an entrepreneur and you’ve learned a lot along the way. 

But this moment tends to arrive pretty quietly, sometimes to our surprise. 

It’s the moment when you realize that the business you’ve poured yourself into for years - the business you worked incredibly hard to build, which may actually be quite successful - doesn’t entirely feel like yours anymore.

Nothing necessarily went wrong. In fact, that’s part of what makes this moment so confusing.

Things may have gone very right. For years, the mandate was relatively simple: to build.

That first season of a business is almost entirely kinetic. You’re solving for survival. You’re figuring out whether the idea works, whether people want what you’re offering, whether you can actually make money doing it.

And there’s something incredibly compelling about that period. There are plenty of problems, but they are concrete. They’re problems, but the answers are out there (actually everywhere) for the having. 

You need more clients. You need a better offer. You need to scale, re-brand or figure out your marketing. 

When it comes to business building itself, there’s always another hill to climb, and by now you’re confident and skilled at navigating this, if not masterful. 

Established founders generally are. You learn the metrics. You learn the market. You develop an enormous capacity for work. You get very good at calibrating the machine.

And it works. Your efforts pay off and the return on your investments makes the machine run smoothly, profitably, and as intended. 

This is when something really interesting can, and often does, happen.

Because over time, after all of that striving and building and becoming, you reflect on what you’ve created and think:

Wait.

Is this actually what I meant for it to become?

Or maybe even more unsettling:

I’m proud of what I’ve built, but…. does this still work for me now?

At a point, many founders pause and appraise, to find that they’re successful, accomplished and high-achieving in all measurable ways, yet still - despite all this - they feel estranged from the business they’ve built. 

I think of this as the dawn of the Second Season.

And one of the deeper truths underneath this transition is that entrepreneurship is not just an economic or strategic process.

It is a developmental process. It carries us through seasons as we travel, but more importantly, as we change.

You may never have considered it in these terms, but you and your business are in a relationship, and relationships carry the power of mutual influence. In many ways, the business becomes a vehicle for your identity expression over time.

In my experience, this - the relevance of our identity development to our business evolution - is wildly underrecognized. 

At a certain point, the question is no longer only “How do I grow this business?”

It becomes “Who am I becoming, and how does this business need to evolve in response to that?”

And that’s where things start to get complicated.

Because one of the reasons this stage can be so disorienting is that we have this enduring mythology around success that says things are supposed to become progressively easier.

You work hard. You become competent. You figure it out. And eventually you arrive at this beautiful place where everything clicks.

Except that’s not really how the founder’s journey works.

Because the business changes, you change, and eventually the problems change too - they become internal, psychological…. even existential. These, however, are not the same problems you became so masterful at solving. Even getting clear about these questions can feel laborious. 

That’s the hidden turbulence of the Second Season.

It’s not necessarily a crisis of competence. Very often, it’s a crisis of context.

Your business has matured, and it isn’t asking you for the same raw external labor that built it anymore.

It’s asking you a much more complicated question:

How does this thing I built fit into the life I actually want now - and into the person I am becoming? 

And that’s a harder question because there isn’t a metric for it. Not exactly, anyway - more on that later. 

But in building and measuring terms, there isn’t a dashboard you can pull up that tells you whether your business still reflects who you are. 

So you can find yourself suddenly struggling with decisions that, five years ago, you would have made in fifteen minutes.

You might second-guess yourself. You may feel numbed out, uninspired, or strangely disconnected from your own voice.

Maybe you start looking for the next strategy. The next growth model. The next coach or advisor. The next thing that will restore that old feeling of momentum.

Because momentum was the old metric - it was reliable, trustworthy and it has always meant you were on the right track.

But now you apply those same strategies and somehow the distance between you and the business gets wider. This is where disconnect gets deeper. You and your business slowly become estranged from one another without the context to understand why.

Not because either one of you is broken. But because both of you have evolved. And very few founders have been taught how to navigate that.

There’s another layer to this that I find particularly fascinating. The first season of entrepreneurship is often fueled by something that looks a little bit like infatuation.

There’s the successful launch. The growth. The money. The recognition.

The feeling of watching something that existed only in your imagination suddenly become real.

It’s exhilarating, rightfully. And as is the case in many relationships - nobody ever tells us that feeling won’t last forever. But the infatuation phase isn’t the relationship.

It’s just the long and lovely beginning of the relationship - when we can let it be. 

Eventually the intensity settles, and what you’re left with is the actual structure underneath it. Eventually it requires a different kind of intimacy, a reframing of commitment. Perhaps even a different kind of maturity.

This is also where identity begins to play a far more central role than most founders anticipate.

Because in the Second Season, what you are actually building is not just a company. You are building a lived expression of identity in motion.

And when your identity begins to shift - as it inevitably will - the business cannot remain untouched by that shift.

In fact, one of the most important watershed moments for many established founders is the realization that their own developing identity must have a role in shaping the next iteration of the business.

Not as an afterthought. Not as a constraint.

But as a primary source design input.

This is why my work using Internal Family Systems (IFS) is so interesting and powerful in the process. IFS offers us a framework for understanding ourselves and others as dynamic - made of varied inner “parts” who have jobs and roles in all we do. We all also have a Self - which is akin to our soul, or bedrock identity. 

In plain terms, through IFS we usually discover that there’s much more happening internally than we are aware of that influences our feelings, behaviors and decisions - and we learn how to work within first, to influence the desired results in our outer lives. 

So when I’m working with a founder in this stage, I’m often most interested in the parts of her that built the business in the first place.

And these tend to be remarkable parts. They’re planners. Executors. Problem-solvers. They know how to keep twelve balls in the air. They know how to push through uncertainty and make shit happen. They’re very often business building superstars. 

In IFS, some of these can be what we call Self-like managers - parts that are so competent, collected and seemingly in command that they can actually be difficult to distinguish from Self.

And I want to be really clear about something here. These parts ARE NOT the enemy.

They may be the architects of your success, and you likely have every reason to love them.

But - and lean in here if you’re drifting because this is essential - the capacities that make these parts extraordinary at building a business also make them surprisingly ill-equipped to guide its evolution.

Not because they’re not brilliant, but because they tend to be very externally-oriented. They’re experts at getting from A to B, but not so skilled at recognizing when the destination itself needs to change.

And this is one of the most important things I think an established founder can begin to understand:

Sometimes the part of you that is exceptionally good at running the business is also the part that cannot imagine letting the business become something else.

And there’s no ill intent there - it’s trying to sabotage you. Quite the opposite.

It’s usually trying to protect everything you worked so hard to build. But aligned business evolution that mirrors & serves your growth? It requires a different kind of leadership.

This is where  the IFS concept of Self-leadership becomes essential. And when I use that term, I’m talking about something very specific.

I mean learning to lead from that calm, clear, confident core that IFS calls Self, rather than allowing our parts to make every consequential decision for us.

Because when that shift happens, decision-making begins to feel very different.

You become less reactive.

Less vulnerable to whatever everyone else in your industry appears to be doing.

Less seduced by the performative metrics of entrepreneurship.

Less interested in building something simply because the entrepreneurial culture around you has decided that bigger is better.

And that requires an enormous amount of sovereignty.

In fact, from the outside, that kind of sovereignty can occasionally look a little bit like not caring.

You might stop caring about certain numbers or opportunities. You might stop wanting the growth everyone assumes you should want or that you once did. 

You might dismantle something that is profitable, to even your own surprise.

You might decide that something you’ve spent years building has completed its purpose.

And from inside the conventional entrepreneurial worldview, some of those choices can look irrational. But there is a profound difference between disengagement and sovereignty.

Sovereignty isn’t “I don’t care what happens”.

It is:

I trust myself with what happens.

I trust myself to make this decision.

And I trust that if I discover later that I didn’t choose optimally,

I trust myself to respond, regroup, to build again.

That is a completely different kind of confidence than the confidence of the First Season. The First Season trains us to think in binaries.

Did it work or didn’t it?

Did we hit the number or didn’t we?

Did we win or lose?

The Second Season asks for something much more nuanced.

It asks you to discern what is actually true for you without immediately filtering it through fear, expectation, convention, or somebody else’s definition of success.

Sometimes that clarity means changing the business model. It may mean changing your role inside the business. Sometimes it means allowing something to end. And sometimes it means realizing that you still deeply love what you built  - you just need to heal your relationship with it.

That is why the Second Season isn’t another, harder mountain to climb. 

The Second Season is a return journey. A homecoming to your sacred Self. 

Because the question begins to change from:

What does this business need from me in order to succeed?

to:

How can I evolve this business in right-relationship with who I am, my deepest desires and a sense of real fulfillment?

And that is a radically different question. It moves us away from building for survival and toward building in alignment with our purpose and inner calling.

It asks us to consider the possibility that rather than your life revolving around your business, that your business should revolve around your life. With YOU at the center. 

You might even find that as I fly that idea, a lot comes up within you. And by all means - please tell your inner managers that we’re not casting strategy and external support to the wind. We still need that, and we still need them. 

But stepping into a different - often unknown - process of change and growth is often deeply necessary for the kind of recalibration the Second Season requires. 

This is why my work with established founders begins internally. There is an inner knowing, or gnosis, sourced from Self, that becomes much easier to hear when the noise around it begins to settle.

Accessing this, and the calm, confident space within that clarifies our next steps may not be in your - otherwise robust and impressive - skillset. 

That’s okay. And this place - accomplished, capable but without the specific support for this unique journey -  is exactly where I found myself once, and it’s why I do this work today. 

Identity evolution is the business development strategy that no one’s talking about. And I think it’s time.

If you do, too, stay in touch and reach out when you’re ready. It would be my honor and joy to support you as your next season of the founder’s journey emerges.