Welcome to Lesson 2 of The Clarity Challenge inside The Purposeful Performer.

To perform at your best as a value creator and revenue generator, you need to identify which phase you’re in—Transition, Build Mode, or Steady State—so you can match your rhythm to the right priorities and pace.

The result? Less stress, better outcomes, and clearer focus on what matters most.

It’s only part two, so we’re still purposefully easing into things.

This is what will give you a strong foundation to a.) stick with The Purposeful Performer philosophy and practice (especially through the Valley of Despair—see below) and b.) build the right type of deep thinking to unlock hidden treasures as we progress (yes, I am doing this with you—along with thousands of others).

Every year, experienced tech sellers begin a new cycle with no guarantee of what’s to come of their performance twelve months later—if they even last that long.

At least 75% of the revenue generators I coached or mentored over the past four years abandoned their personal operating system too soon, pressured by a phenomenon known as The Emotional Cycle of Change.

Today, we’re exploring three key phases you’ll encounter throughout your journey—Transition, Build Mode, and Steady State—and how understanding where you are can shape your strategies and expectations.

Think of it like shifting gears in a car: you can’t cruise on the highway in first gear, and you can’t climb steep hills in fourth gear.

You’re juggling big deals, personal milestones, and a vision of what you ultimately want to do if you could venture out on your own. If you can be clear about what phase you're in, you can get intentional about managing it effectively.

This will have a huge impact on:

The three phases look like this:

Note that there is a fourth phase you may find yourself in at some points in your life: the Explore phase. This is when you are either intentionally or unintentionally between roles or major seasons of life, when the majority of your time, energy, attention, and money are directed toward deeper alignment with your authentic self, and when you may find yourself asking the bigger questions in life.

Why am I here?

What is my purpose?

Who matters most in my life?

How can I live up to my purpose and be at peace?

That phase is undoubtedly crucial, but it is also a highly personal journey, so it is not for me to provide you with any actionable advice or playbook; rather, it is for you to explore the depths of your inner self to change your outer world.

We move between these phases multiple times as we progress in our careers and climb the three key levels of authentic autonomy—Learn, Earn, and Evolve. How fast we traverse all three levels is highly individual.

There are nature and nurture factors that contribute to the pace. Some things we can control. Others we cannot. Zoomed in to the day-to-day, these factors may feel “bad” or “good.” But zoomed out really far, we discover they just “are.” The sooner you realize this, the lighter you can be (and the faster you can move).

Ok, that might be a bit too philosophical and meta, so let’s bring it back down to earth in practical terms.

The Three Levels of Autonomy Architecture: This is the framework I use to anchor us to where we are in our careers as value creators and revenue generators. In the simplest terms, we can measure our progress by ownership of the most ubiquitous tool we all use to do our job—the calendar.

The Three Phases: Now, there is no exact science to the number of times you may cycle through all three in a given Level, but you will need to work through all of them successfully to progress through each level.

Warning: You’ll want to avoid stagnation, complacency, and boredom, so don’t stick around phase three for too long. The goal is to oscillate back to phase two and one appropriately, and then ladder back again with a new set of capabilities.

Find a harmony between having enough roles that give you the experience and challenges you seek, with enough stability and space to apply that experience and generate leverage.

Here’s a simple way to think about it:

The key to finding this harmony is becoming elite at timing. And timing things right relies on deeper awareness (of the inner self and the outer world). And deep awareness is fueled by a purposeful operating system that applies a core principle to our philosophy here—Human First, Professional Second.

The traditional onboarding sales process employed by most tech companies sucks.

I can attribute my MVP award and achieving 177% of target in my first year as a Strategic Account Director at LivePerson to bucking the normal onboarding trend.

I call this "canvassing"—trying out small ideas and experiments based on what you learn as you deeply educate yourself about your company's point of view (you need to turn it into your own) before you start on the job.

The traditional onboarding process for most tech sellers is one designed around taking it slow out of the gates and immersing yourself in the product only once you start.

The problem with this approach is that it lulls sellers into a false sense of security, leading them to feel they can take it easy and build their point of view and territory thoughtfully at their own pace. But the pressure starts mounting as quickly as month four, and your well-meaning strategy gets decimated in favor of an uninspired, high-pressure, and activity-driven approach forced down from the top.

The power completely shifts out of your hands, and by that point, it’s tough to gain it back. I’ve witnessed sellers even get fired within their first six months, even though they thought they had more time to build their book of business.

The problem in these situations is that these sellers aren’t operating in the right phase at the right time.

Let’s unpack a better way so you never find yourself in this vulnerable position.

In the past, I’ve shared the story of how I landed an exciting deal with Aramark using my existing connections at Apple.

The key was to alert them to my intentions before I even started in my new role (Transition Phase). That allowed the opportunity to come to me (literally on my first day) and give me something tangible to work on immediately (Build Phase).

The other opportunity won in that first year was the ​Delta Air Lines deal​ that leveraged the infamous ​Open Letter approach​. That opportunity materialized because I requested it and solidified my account list before joining.

See a trend emerging here?

A lot of the juicy work that made an impact in my first year as a strategic seller happened before I even got my laptop and office badge.

The key driving principle was to move fast when others were slow, so that I could slow down later when everyone else was fast and frantic.

What exactly did that look like?

The first step was knowing I was in the right environment by doing proper due diligence to evaluate this new opportunity on LivePerson’s newly formed Strategic Accounts team against my old Enterprise AE role, where I was relatively comfortable (Steady State … but getting stale).

Doing that careful process made me feel confident that I was making the right decision with this new role and setting myself up for future, upward mobility (which would further unlock more authentic autonomy in my life).

The next step was to give myself ample time between my old role and the new one. Between accepting the new role as a Strategic Account Director and my official start date, I gave myself a month to recharge and refocus.

Note: I call this Recovery. You could argue this is its own phase, but I think of Recovery as the “in-between” parts between each phase. They’re crucial.

My wife and I spent a week in Napa Valley, where I completely decompressed, and then when I got back home, with three weeks still left before my start date, I got to (deep) work analyzing LivePerson’s value proposition, watching the CEO on interviews with CNBC, and studying their largest customer.

​I practiced owning the CEO’s point of view as my own​ … until I had a perspective, narrative, and talk track that was indeed my own—one compelling enough to get high-level executives to notice and take action.

The third step was to come in ready to execute at a fast, but purposeful pace out of the gates (Build Mode). That “pre-season” work paid off handsomely (literally).

While my peers were still getting up to speed on how the product worked and fully understanding the value proposition, by the end of February (I started on January 15th), I already had two meetings with Aramark, one with Facebook, one with IBM to pursue Apple, and opened dialogue with Delta.

These real-life business conversations taught me more than any onboarding videos, slides, or mock exercises could.

At the end of that first year, I was the only seller on our team to surpass their number and was awarded MVP. This trust further enabled me to secure new opportunities that passed the desk of my C-Suite, and my performance earned me a promotion to VP (without having to manage a team).

That first year of purposefully moving fast put me in a position the following year to earn more than I ever had as a corporate seller ($1.2M+ in commissions and $1.5M+ in gross income), then slow down, be more methodical in my approach, and operate on my terms from that point on (Steady State) until I started building my personal brand and transitioned to Level III autonomy in 2022.