The Messy Middle

Your Next Chapter Doesn’t Come with Instructions

Sometimes life takes one look at the plan you carefully created and says, “That’s cute—but we’re doing something different.”

You lose the job. You retire. Your children leave home. Your body changes. A relationship ends. You become a caregiver.

Or maybe nothing dramatic happens. You simply wake up one morning and realize the life you created no longer feels like the life you want. The old version of you doesn’t quite fit anymore, but the new version hasn’t shown up with a name tag and an instruction manual.

I know that feeling. So does my husband, Pablo.

The same week I was downsized from my corporate job at 58, Pablo retired from Procter & Gamble after 33 years. Under the same roof, we were facing two very different endings—and the same underlying question:

Who am I without the role that shaped so much of my life? And, now what?

Neither of us received a roadmap. We had to figure it out as we went. Honestly, we still are.

The event happens. The adjusting takes longer.

One idea from the Modern Elder Academy’s work on transitions has stayed with me: change and transition are different experiences. Change is the event. Transition is the internal process of adjusting to what that event means for your identity, routines, relationships, and future. The change might happen on a Tuesday afternoon. Understanding how to live with it can take months or years.

The ending, the messy middle, and the new beginning offer a useful way to think about that process. But don’t expect a straight line. We can move forward, circle back, get excited, panic, and question everything. Sometimes all before lunch.

What I lost—and what I still had

When I was downsized, I lost more than a position. I lost a familiar structure, relationships with coworkers, a professional identity, and the future I assumed I was moving toward. On the surface, I was asking, “What am I going to do now?” Underneath, I was trying to understand who I would be next. I could have interpreted the loss as a signal to wind down. I was approaching 60. Maybe I was supposed to start thinking about retirement. But that didn’t feel like me.

I still had energy, ideas, goals, and more than 35 years of experience in aging services. I had something meaningful to contribute, and I wasn’t ready to disappear. So I started a care management business because nearly 20 years in corporate roles had left me too far removed from direct care. I wanted to understand exactly what it was like for older adults and their families today. For years, I had helped organizations develop programs and services for older adults. I talked about aging and researched the issues. But what did I really know about the realities? I knew I needed to get back into the weeds: sit across the table from families, walk through the system alongside them, and understand what aging in America looked like when life became difficult. And boy, was I surprised.

I saw families being passed from one provider to another, often with no one looking at the whole picture. Quality care was expensive. Resources were limited. Older adults had complex needs that didn’t fit neatly into a program or service. Families were exhausted from trying to hold everything together. By the time many reached me, they were already in crisis. Their choices had narrowed because of declining health, depleted finances, caregiver burnout, or decisions postponed for too long.

The work mattered deeply, but it was also exhausting, frustrating, and sometimes incredibly difficult.  I loved every minute of it. However, I could only help a handful of clients at one time, and the needs are massive. At this stage of my career, I also wanted a little more freedom in my schedule to travel with Pablo, so I began to shift my priorities.

I began to notice that few people were focusing on helping the younger crowd (50+) with how they can influence the course of their personal aging journey through lifestyle changes and mindset. I was following all of the longevity gurus and healthspan experts, and the seed inside my brain kept growing, keeping me up at night. The light bulb went off, and I founded Bold, Not Old™to offer a blueprint and voice for anyone who wants to design a life worth growing older for. I have found my happy ending.

Pablo’s ending was different. He chose retirement after a career that began in Mexico City and took him around the world as an engineer. His work provided structure, responsibility, relationships, intellectual challenges, and a clear way to contribute. Leaving it created freedom, but it also meant leaving behind a daily life he had known for more than three decades.

You don’t simply turn off your computer, sleep late on Monday, and instantly know who you are supposed to be next.

Even an ending you want and looked forward to can leave you unsettled.

Pablo’s exploration looked different. After retiring, he gave more attention to his health. Yoga became part of that process, helping him work on strength, flexibility, balance, and resilience. It also opened an unexpected possibility.

This year he completed his 200-hour yoga teacher certification. He didn’t leave P&G carrying a briefcase in one hand and a yoga mat in the other. That direction emerged because he gave himself permission to explore.

That’s why I think we need to give endings some room. Before rushing into the next thing, it helps to ask:

• What am I leaving behind?
• What am I grieving?
• What did this chapter give me?
• What do I want to carry forward?

Welcome to the messy middle

This is the space where the old life no longer fits, and the new one isn’t clear yet.

I would have preferred a checklist and a guarantee that everything would work out. What I had instead were questions.

• How did I want to use everything I had learned?
• What did I want to contribute?
• What kind of work could I keep doing with energy and conviction?

You do not need to know the final destination before taking the next step.

Take a class. Volunteer. Revisit an old interest. Have a conversation with someone doing work that intrigues you. Try something without requiring it to become your next career or permanent identity.

Then pay attention. What gives you energy? What do you want to do again? What sounds appealing in theory but doesn’t feel right in practice? Those answers give you somewhere to go.

Becoming someone new, with everything you already know

For me, becoming a business owner involved much more than registering an LLC and creating a website. I had to begin seeing myself as a speaker, coach, writer, and founder—someone who could create work around what she believed without waiting for an organization to assign her a role. Do I have everything figured out? Absolutely not. I still have uncertain days. I question myself. I occasionally wonder what on earth I’m doing. But I keep returning to the work and the people I want to reach.

Pablo is stepping into his identity as a yoga instructor. His engineering experience hasn’t disappeared. He brings his patience, discipline, curiosity, and love of learning into a different setting. Neither of us has had to erase who we were to become who we are now.

We are starting from experience. That matters after 50, when it can be easy to look at the years ahead and underestimate everything the years behind us have given us.

A transition touches more than one part of your life

The Modern Elder Academy’s six P’s offer another useful way to reflect on what is shifting. These are the questions I would bring to each area:

Personal: Who am I now, and who am I becoming?

Professional: What place do work, service, and contribution have in my life?

Physical: What does my body need during this season?

People: Which relationships are changing, and who supports me as I grow?

Place: Does where and how I live support the life I want?

Purpose: What gives my days meaning and direction?

My professional transition changed my identity, relationships, routine, and sense of purpose. Pablo’s retirement affected those same areas in different ways.

That is why I keep saying that retirement planning cannot be only about money.

Financial readiness matters. So does life readiness.

We need to think about how we want to spend our days, who we want around us, how we will care for our bodies, and what will make us feel useful and connected.

What is your next step?

If you’re in transition, you may feel pressure to produce an answer to “What’s next?” before you’ve had time to understand what has ended. Give yourself room to reflect. Then choose something to try.

Ask yourself:

• What am I ready to release, and what do I want to carry forward?
• What could I explore without demanding an immediate answer?
• Which of the six P’s needs my attention right now?
• What is one small action I can take this week?
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You do not need to map your entire future today. But you can take a step toward a life that feels more like your own.

Pablo and I are still writing our next chapter. Some days are clearer than others. What keeps us moving is the willingness to learn, try, adjust, and stay curious about what comes next.

That is part of what Bold, Not Old™ means to me.

Aging is inevitable. How we age is influenced by the choices we make every day—including the choice to begin again.

What transition are you navigating right now?

Acknowledgment: This reflection draws on the Modern Elder Academy’s work on transitions and its six P’s framework. The distinction between change and transition, and the stages of ending, the neutral zone, and a new beginning, are central to William Bridges’s transition model. The personal stories and reflection questions above are my own.