In early January, my friend Cameron Uganec encouraged me to connect with Steve Pratt—author, strategic storyteller, and what we’ll call an “Attention Architect.” Cameron believed Steve’s journey through a bold career transition would resonate with our readers, and I think he was right (ok, he usually is). Steve had recently stepped away from his leadership role at Pacific Content, a trailblazing podcast consultancy he co-founded that partnered with brands like Dell Technologies, Charles Schwab, Adobe, and Ford. Stepping out on his own, Steve’s leap into a new chapter isn’t just inspiring, it is filled with practical insights and lessons for anyone navigating their own career or life shifts.

Steve and I hit it off immediately. We discovered we share a connection through Page Two Publishing, the team behind his book “Earn It” and an incredible partner as we build the Inhabit brand. What stood out to me most in our conversation was Steve’s willingness to embrace uncertainty and his thoughtful approach to making a major life pivot. His story reflected many of my own experiences, and I could tell we’re both deeply invested in creating meaningful, authentic work.

We had a great time walking through his seven insights. We didn’t just swap stories; we got to the heart of what really worked for him during his journey. His insights are practical, actionable, and grounded in the real challenges of navigating change. So whether you’re just starting to think about a new chapter or already knee-deep in the middle of one, these ideas can serve as a roadmap to finding greater clarity and moving forward with focus.

Over my 17 years in recruitment, I’ve had a front-row seat to countless career transitions. Some people move through them with confidence and purpose, while others struggle to find their footing. What I’ve learned is this: success in these moments almost always comes down to how much time and energy people invest in the deeper questions—the ones like Steve has put forward. These are questions that make you pause, reflect, and dig into what you really want in your next chapter.  

Without further ado, here are Steve’s seven insights: 

1. Transitions are messy—and that’s okay

When Steve and I started discussing transitions, he brought up William Bridges’ “Transitions” and how it completely shifted his perspective. “Most people think transitions go Beginning → Middle → End,” Steve said, “but Bridges shows us they’re actually Ending → Middle → New Beginning.”

I asked him what made the middle so critical, and he didn’t hold back. “The middle is where it all gets messy,” he said. “It’s uncomfortable, and people don’t understand it. You’re out of one story but not yet in the next one. It’s tempting to rush through it, but that middle space is where the breakthroughs happen.”

I could tell this wasn’t just theory for Steve—it was personal. When I asked him to share more about his experience, he shared: “When I went from 100% to 0%, it was a shock to my system. The middle is tough because you don’t have an identity there. You feel lost, and you just have to push forward.”

“The middle takes time, and if you rush it, you’ll probably end up back where you started, doing what you were doing before. You have to let it unfold.”

I asked him what advice he’d give to someone trying to navigate that phase. “It takes longer than you think,” he said. “The middle takes time, and if you rush it, you’ll probably end up back where you started, doing what you were doing before. You have to let it unfold.”

Key takeaway: The middle is messy, uncomfortable, and essential. Don’t rush through it. Let it do its work so you can truly move forward. Don’t short-circuit the process just to feel like you’ve moved on.

2. Ask the tough questions

When I asked Steve how he started figuring out his next chapter, he thought for a moment, and said, “You have to ask yourself the tough questions. And you have to be honest—really honest—even when it’s uncomfortable.”

Steve explained that it wasn’t just about the questions themselves but about sitting with the answers, even when they were messy or hard to face. “Who am I? What do I truly value? Where do I excel? And what kind of work makes me lose track of time because I’m so engaged? But if you sugarcoat your answers,” he continued, “you’re not helping yourself. If you downplay what’s real, you stay stuck. The truth, even when it’s uncomfortable, is what sets you free.”

The process didn’t stop with identifying what mattered. It also required unlearning and letting go. “I had to ask, what do I need to let go of? What do I need to unlearn? Where am I still operating on autopilot, using outdated programming?” Steve said. “For so long, achievement was my compass.I had to stop and ask myself, is this even what I want anymore? Or am I still chasing something I no longer believe in?”

“I realized I was still holding on to old metrics, old measures of success that didn’t align with who I am now,” Steve admitted.

He told me about reading Oliver Burkeman’s “Four Thousand Weeks” and how it introduced him to the idea of being an “insecure overachiever.” That phrase hit home. “I realized I was still holding on to old metrics, old measures of success that didn’t align with who I am now,” Steve admitted. “Letting go of that mindset wasn’t easy, but it was the only way to create a future that felt true.”

Steve emphasized how important it is to sit in the discomfort of these questions. “You can’t rush it. You have to be willing to take a really hard look in the mirror. If you aren’t honest, you’re just spinning your wheels. But if you face the truth, that’s where clarity begins.”

Key takeaway: Ask the questions that matter, and don’t shy away from the hard answers. The discomfort of honesty is what moves you forward—it’s how you let go of what’s holding you back and step into what’s next.

3. Reassess what’s truly important

Steve again referred to Burkeman’s work as a game-changer during this transition. “Four thousand weeks—that’s the average human lifespan,” he said. “Realizing I couldn’t do everything forced me to focus on what truly matters.”

This clarity wasn’t limiting—it was freeing. “It helped me let go of the noise and focus on what I’d truly regret not doing,” he explained.

Confronting mortality “feels unnatural,” Steve admitted, and it is uncomfortable but necessary. “It’s about giving yourself permission to live the life you actually want, not the one you think you’re supposed to want. Your life is what you pay attention to. If you’re wasting time on things that ultimately don’t matter, you’re wasting precious time.”

When Steve mentioned the book “Die With Zero” by Bill Perkins, it was clear this book left a lasting impression. “It completely reshaped how I think about time, money, and experiences,” he said. “The earlier you create the experiences you want, the better. Memories, like compound interest, grow richer over time. But if you wait too long, you risk missing out entirely. It’s not about stockpiling money for some imaginary scoreboard. It’s about living deliberately and focusing on what truly matters.”

It’s not about the balance in your account—it’s about the balance in your life.”

Steve left me with this thought: “If you die with lots of money in the bank, that might just mean you spent days working when you could’ve been spending time doing things that matter to you and your people. It’s not about the balance in your account—it’s about the balance in your life.”

Key takeaway: Examine where your time, attention and energy are going. Let go of what doesn’t align with what matters most. Life is what you pay attention to, so focus on creating meaningful moments now.

4. Lean into your life learnings

Steve shared how Arthur Brooks’ “From Strength to Strength” introduced him to the concept of two intelligence curves:

• Fluid intelligence: The ability to solve problems, innovate, and rapidly learn, which peaks in our younger years.
• Crystallized intelligence: The capacity to synthesize ideas, teach, and mentor, which grows as we age.

“As fluid intelligence starts to fade, crystallized intelligence becomes a strength,” Steve explained. “Recognizing this shift helped me see where I could add the most value in this next chapter of my life.”

Key takeaway: Don’t cling to the skills that defined your early career. Instead, lean into the wisdom and perspective that make you uniquely valuable now.

5. Stand out by being yourself

“The job market is increasingly dominated by AI-generated resumes being reviewed by AI-powered recruitment platforms, creating an environment where everything feels impersonal and generic,” Steve said. “But the best opportunities? They don’t come from blending in—they come from standing out.”

“What are your quirks? What makes you weird? That’s what makes you memorable,”

Steve explained that standing out starts with embracing your uniqueness. “What are your quirks? What makes you weird? That’s what makes you memorable,” he said.

He reflected on how this realization unfolded within the company he founded. "Over time, my role shifted to focus more on systems and operations—areas that didn’t align with my strengths. That was a wake-up call. It made me realize I needed to rethink my place in the business and find ways to contribute that felt meaningful and energizing."

This shift in focus also aligned with the concept of crystallized intelligence—the wisdom and expertise we build over time. Writing a book, crafting newsletters, and coaching others in their careers became conscious choices to lean into this intelligence and see how it resonated. (Spoiler: It feels amazing!)

When Steve stepped away from his role at Pacific Content, he didn’t just look for the next job posting. He took the time to design a future that reflected who he truly was. “I started by asking myself: What am I great at? What am I curious about? What’s the intersection where I can create the most value?”

He found “Designing Your Life” by Bill Burnett and Dave Evans particularly helpful. “That book opened my mind to possibilities I hadn’t considered. It’s about giving yourself permission to think differently. I started mapping my interests and exploring possible combinations. The idea wasn’t to come up with one perfect answer but to realize the freedom in knowing you could come up with 50 options if you wanted to. That realization is what sets you free to imagine something bigger than the conventional path.”

It’s not always about finding your next step, it’s about creating it. “When you realize the possibilities are endless,” Steve said, “it frees you to start shaping a path that feels right for you.”

Key takeaway: Embrace the freedom that comes with thinking beyond traditional career paths. Your unique skills, passions, and quirks are what make you stand out. 

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6. Put yourself out there

Once you’ve identified your unique strengths, Steve’s advice is clear: “Share them generously.” Whether it’s writing, speaking, posting on LinkedIn, or starting a podcast, Steve underscored the importance of putting your expertise out into the world. “Sharing your ideas not only builds credibility but also attracts opportunities,” he explained.

This struck a chord with me because we’re both in the process of bringing something new to the world. Steve’s approach isn’t about chasing visibility for its own sake; it’s about creating meaningful connections. “When you’re generous with your thoughts and expertise, things have a way of showing up,” he said. “It’s not about having a programmed outcome. It’s about putting your ideas out there, contributing your voice, and trusting the process.”

“Not everything has to be strategic or tied to a specific goal. Sometimes, it’s about taking risks and sharing what excites you, trusting that the right opportunities will emerge.”

Steve acknowledged that adopting this mindset required a shift in thinking. “I had to let go of my achievement orientation,” he admitted. “Not everything has to be strategic or tied to a specific goal. Sometimes, it’s about taking risks and sharing what excites you, trusting that the right opportunities will emerge.”

This approach is a reminder that we don’t always need to measure our actions against immediate outcomes. Steve framed it this way: “Sharing your expertise and insights isn’t about controlling what happens—it’s about creating possibilities.”

Key takeaway: Be generous with your expertise and ideas. Focus on connection rather than control, and trust that by sharing your voice, the right opportunities will come your way.

7. Bet on yourself

Steve’s final insight might be the boldest of all: if you don’t find the opportunities you want— create them. “It’s scary to go out on your own,” he admitted. “But if you’ve done the work to figure out your value and share it, betting on yourself can be one of the most rewarding things you’ll ever do.”

“When you lean into what makes you unique, you realize something profound: the job that would suit you best probably doesn’t exist. And that’s okay.

He talked about the clarity he found in Paul Jarvis’ “Company of One,” a book that shifted his thinking about what it means to create work on your own terms. “When you lean into what makes you unique, you realize something profound: the job that would suit you best probably doesn’t exist. And that’s okay. It means you get to create it. That’s where the magic happens—you get to build the life and work that reflect your values, your expertise, and your passions.”

Steve emphasized the freedom that comes from stepping outside the traditional paths. “Sometimes, it’s about putting your ideas into the world, sharing what you know, and seeing what takes shape. When you do that, you might discover there’s a shortage of people who bring exactly what you bring—and that gives you the chance to create something entirely your own.”

Beyond career advice—these words were an invitation to live differently. To build something you’re excited about, something that feels like you. “The best opportunities don’t always come knocking,” he said. “Sometimes, you have to make them happen.”

Key takeaway: The work you’re meant to do might not exist yet. By leaning into what makes you unique and sharing it with the world, you can create a future that’s fully yours.

Change isn’t easy, but it’s worth it

As Steve and I wrapped up our conversation, something profound surfaced: navigating a career transition isn’t just about finding your next move—it’s about discovering who you are and aligning your life with that truth.

Change is uncomfortable. It’s messy. It stretches you in ways you didn’t expect. But it also opens up space for something better, something richer, something more you.

If you’re in the thick of it, I hope these ideas and stories light a spark for you. And if you’ve already walked this road, I’d love to hear what guided you forward, what helped you hold steady in the chaos.

The discomfort, the uncertainty, the messiness—they’re all part of the process. They’re what make the transformation real. And when you lean into it, when you embrace the work of change, you open the door to the life that’s been waiting for you all along.

Steve Pratt’s recommended reading list

Here’s a list of books that guided Steve through his bold career transition. 

1. Transitions: Making Sense of Life’s Changes by William Bridges
   William Bridges takes us deep into the emotional and psychological process of change, breaking it down into three profound phases: ending, middle, and new beginning. It’s an essential guide for anyone navigating the messy, transformative work of letting go and stepping into something new.
2. Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman
   Burkeman reminds us of the simple yet staggering truth: we only get about 4,000 weeks on this planet. By facing the reality of our limited time, we can focus on what truly matters, let go of what doesn’t, and live with intention instead of distraction.
3. From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life by Arthur C. Brooks
   Arthur Brooks maps out how our intelligence evolves over time, from the hustle of youthful problem-solving to the wisdom of teaching and synthesis in midlife. This is the book for anyone ready to embrace their next chapter with clarity and purpose.
4. Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett and Dave Evans
   Life isn’t something you find; it’s something you design. Burnett and Evans use design thinking to help you uncover your “what’s next,” combining your skills, passions, and curiosity to build a life that’s uniquely yours.
5. Company of One: Why Staying Small Is the Next Big Thing for Business by Paul Jarvis
   Paul Jarvis turns the traditional business narrative on its head, showing that success isn’t about scaling up—it’s about creating a meaningful, sustainable life that works for you. This book is a blueprint for building autonomy and purpose into your work.
6. The Element: How Finding Your Passion Changes Everything by Sir Ken Robinson
   Sir Ken Robinson takes us to the intersection of passion and ability, urging us to embrace our unique “element.” When you find what lights you up, the path forward becomes extraordinary.
7. The Middle Passage: From Misery to Meaning in Midlife by James Hollis
   Hollis explores the deep shifts that come in midlife, inviting us to move from external definitions of success to inner meaning. It’s a reflective, profound guide for turning crisis into growth.
8. Dare to Lead by Brené Brown
   Brené Brown challenges us to lead with courage and vulnerability. Whether you’re stepping into a new chapter or reimagining your role, this book offers the tools to navigate uncertainty while staying grounded in your values.‍
9. Die With Zero by Bill Perkins
   Perkins asks a bold question: what if we stopped hoarding our time and money for “someday” and started creating memories now? This is a guide to living fully, focusing on the moments and experiences that make life worth it.

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