Piloting Your Life: Chapter 1: Journey

Terri Hanson Mead
Terri Hanson Mead
Published in
15 min readJun 24, 2020

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Terri in her home office sporting the fabulous Piloting Your Life aviators

This is an excerpt from Terri Hanson Mead’s multi-award winning book Piloting Your Life. Terri wrote the book as a love letter to GenX women to embolden women over the age of forty to take the controls and be the pilots in their own lives.

To read the rest of the book (or listen to it), order on Amazon (ebook, paperback, audiobook narrated by Terri). For other purchasing options, go to the Piloting Your Life website.

CHAPTER 1: THE JOURNEY
While talking with a friend about how all of us have circuitous and serpentine life routes, an image of the Life board game popped into my mind. I used to love playing it when I was younger. Now, I just find it frustrating as it takes so long to play. Even so, it seemed like the best analogy to pull into the book here.

Let’s assume we start at the point in the game when we’re alone in the little car. Pick your peg color. Pink or blue. Off you go with the first spin of the spinner. In the game, you’ll pick up passengers along the way in the form of a spouse and/or kids. You’ll draw cards to determine your career, any extra earnings, and payments. The goal is to move from space to space as you head toward the final stop: Retirement.

I’d like to see a more modern version of this game with other colored pegs. Let’s bring in other realities like death and divorce. (I suppose that would ruin a game for kids.)

We still have half our lives left to live when we reach midlife. Thinking about decades of open terrain can be terrifying and overwhelming. If you think about it too much, it can send you into an anxious spiral.

In reality, life is a game of chance, luck, and effort that unfolds daily. It begins with birth and ends with death. In between, it’s a wild ride of opportunities shaped by our families, our environment, and how we handle what’s offered.

Earlier in our lives, standard societal milestones keep us on a predictable path. In midlife, the field opens up, and we encounter wide, open terrain that lasts for decades. It becomes up to us to gauge our progress and personal success. We define the checkpoints. This can be quite intimidating. Most of us don’t acknowledge this wide-open space and want the unidentified and unnamed discomfort to just go away already.

What if we broke midlife (and the rest of our lives) down into five or ten-year segments? Wouldn’t that make it easier to manage? We can have long-term plans, but we don’t have to have everything figured out.

How do you eat an elephant? One bite at a time. Have no idea where to start? Hold tight; I have ideas for you in some of the later chapters.

As you begin to rethink and reframe your midlife — and the rest of your life — here are some things to keep in mind:

— It’s a journey, not a pivot.

— As one chapter ends, another chapter is just beginning.

— Anchors provide stability in times of change and transition.

— You have to be willing to step into the unknown.

— It’s worth the effort.

— All the pieces will come together.

Ready for a deeper dive?

IT’S A JOURNEY, NOT A PIVOT

Four years ago, when I decided that I wanted to do something more with my professional life, I took steps toward what I naively called a pivot. I assumed that whatever I was working toward would ultimately end in something … at which point I would be done. I felt overlooked, dismissed, and frustrated in my professional life. I was afraid I was becoming irrelevant and wouldn’t be able to provide for my family, our current lifestyle, our future, and eventually, retirement.

That discomfort needed to die.

So, I tried making those yucky feelings go away by filling my life with lots of activities. Surely, achieving that one thing, that next thing, would make it all better.

Not so.

Last year at Startup Grind, a conference in my hometown, I bumped into my friend Susan. She asked me, “When is your pivot going to be done? I think you should have an end date.”

Startled by the question and the pressure, I boldly said, “Well … it’ll be done at the end of the year.” After that, I started marching toward completing my pivot …

…until I completely forgot about the commitment.

Fast forward a few months. I’m interviewing one of the women for this book, and the topic of pivoting came up. “I’m four-and-a-half years into my pivot,” she said. That’s when it hit me.

Midlife isn’t a pivot.

It’s a journey.

I held the delusional belief that if I changed just one thing, all would be well. I wanted to get rid of my midlife angst as quickly as possible and was looking for the magic bullet.

While I’d been working so hard to avoid the uncomfortable feelings, what I really needed to do was stop fighting them and see what they had to tell me. That’s hard, by the way. Our minds naturally want to rid themselves of discomfort. We have to fight that natural response and stay with the feelings. We needn’t be afraid of losing ourselves in the uncomfortable feelings; it doesn’t work that way. In fact, when we sit with them, we tend to discover ourselves.

When my husband and I were deciding when to have children, I kept saying, “I’ll be ready when I lose ten pounds.” Which morphed into, “I’ll be ready after I get this promotion,” or “once we have more money saved.”

My wise friend Linda said, “There is never the ideal time to start a family. Stop waiting, decide, and go for it. You’ll only regret it if you keep waiting.”

She was right.

The same holds true in midlife. There will never be a perfect time to focus on you. There will always be one more thing to do and one more person to care for. Something will always get in the way of choosing your own path.

It’s up to you to make your journey your priority. Not later. Now.

BEING INTENTIONAL

For a lot of women, midlife is when we finally feel free to take time for ourselves.

Jacqueline felt she was in a holding pattern while raising her kids. She loved volunteering in the classroom and leading nature-journaling for second graders, but as her marriage fell apart and her kids grew older, she knew she needed to make changes.

She said, “I didn’t know what I wanted to do, and I didn’t know where to start. I only knew I didn’t want to go back to the career I had before I had kids.”

She dabbled in a few things, and with each new experience, she learned and applied her newfound knowledge to the next experience. As the reality of her new situation set in, she knew she needed to be more intentional about making money and building a career. She said, “I wanted to be able to provide for my daughters and create a stronger financial future for myself. I wanted my work to be meaningful and impactful. To do this, I knew I had to take seriously the work of finding work.”

Now, with one daughter headed off to college and the other not far behind, Jacqueline has ended her primary focus as a stay-at-home mom. She’s shifted her attention to what she wants in work, love, and play.

“I feel like I’m just getting started on my journey, and I’m forty-nine!”

Of course, she doesn’t have it all figured out. Every day is a new challenge, but she’s embracing the change, the opportunities, and looks forward to what’s next with hope and excitement rather than fear and avoidance. She is intentional about how she spends her time and where she puts her energy, which brings her closer to what she wants in and out of her life.

The key is to have a deliberate mindset around appreciating where you are (gratitude, anyone?) and optimistically looking forward to what is coming next. This isn’t easy. It requires attention to self-care, patience, and finding something stable while everything changes, which brings us to anchors and tie-downs.

ANCHORS AND TIE-DOWNS

In my forties, I made many pivotal decisions, including accepting an invitation to join a group called Change Makers/Rule Breakers for a week on Necker Island, one of Richard Branson’s private islands in the British Virgin Islands.

While the island is a beautiful and special place that very few people get to visit, it was the time spent with Richard and the others that led me to search for more. At Necker Island, I began to look at the world differently. Having only ever lived in the San Francisco Bay Area, my worldview (and my view of myself) was somewhat limited. Going to Necker changed that for me. And, indirectly, led to this book.

The first invitation came in 2016. I jumped at the chance, booked flights, and sent my payment before I could talk myself out of it.

Despite my fears and misgivings about it being too good to be true, I ended up on the island with thirty amazing people from around the world. I even partnered with Richard Branson on the tennis court.

One day, after lunch on Moskito Island (one of Richard’s other private islands), I relaxed on a lounge chair and gazed out across the sparkling, aquamarine channel. A deserted island on the other side beckoned. I could almost hear it saying, “Swim to me, Terri.”

Who can resist that?

I didn’t tell anyone. I didn’t know how I would get back. I just took off my cover-up, left it on the lounge chair, walked down to the water, and started swimming. While swimming, I glanced back a few times to see if anyone was calling me to turn back. At the halfway point, I let go of the pull back to the safety of Moskito Island and kept going.

Three-quarters of the way across, I realized I would be too tired to swim back. I didn’t worry about it; I’d figure that out when I got to the beach. I was within shouting distance of the shore when two men in a small speedboat drove up to the beach and started to unpack their things. I yelled at them to hold up, stepped out of the water (I wish I looked like Bo Derek, but I’m pretty sure I was panting like a swamp thing), and asked if they would give me a ride back to Moskito.

After the two brothers from Florida got over the surprise, one of them said, “Hop in! We’ll drive you back.”

So, I did.

Back at Moskito, I hopped out and said thank you, and they zipped away as I walked up to the bar for a well-deserved drink. Despite being parched and tired, I felt victorious.

As I swam, I kept looking back for someone to tell me I couldn’t swim across the channel. I expected someone to tell me I couldn’t be on the deserted beach. With this swim, I realized I didn’t need anyone else’s permission. This was a powerful moment for me. Permission was mine to give, to myself. With that realization, I cut one of the tie-downs holding me back and moved a few steps closer to the freedom to choose my own path on my journey.

Sometimes we just have to get out of our own way.

When we go through transitional periods like midlife, the work is often difficult. Anchors help us ease into the transition by creating a feeling of certainty. But sometimes anchors aren’t what they seem.

In other words, don’t confuse anchors with tie-downs.

The definitions of each of these terms are very similar … but are actually very different. An anchor provides stability; tie-downs hold you back. If an anchor is keeping you from making progress, over time, it becomes a tie-down.

As I let go of tie-downs and experience turbulence in my life, I’ve added anchors like daily meditation and stretching, regular communication with friends, and morning pages (daily journaling) to provide me with something constant as everything around me changes. When I start to feel blown about and out of control, I come back to these things. For you, it might be getting out into nature, taking a walk, yoga, or other similarly healthy and grounding activities.

STEP INTO THE UNKNOWN

The Covey Club Reinvent Yourself podcast became a big inspiration for me as I conducted my research for this book. Host Lesley Jane Seymour interviews women over the age of fifty who reinvented themselves. She covers everything from a very public firing (Sallie Krawcheck), to an empty nest (Jeannie Ralston), to leaving corporate (Randi Levin), and more.

One of her guests, Louise Phillips Forbes says, “Step into the unknown, and say yes. Own who you are, and be willing to show up and do the work. Have faith in the process, and when you follow your passions, one dream will lead to another.”

So much becomes unknown and unfamiliar in midlife. That won’t change, so we might as well accept the discomfort, experiment, and explore. We can’t wave a magic wand and make it just so.

No bippity-boppity-boo for us.

We have to actively take steps, often into the unknown, and see where they lead. Then we take it from there.

BETTER ENDINGS LEAD TO BETTER BEGINNINGS (WE SUCK AT CLOSURE)

As a technical project manager, I find rhythms in every project I manage.

After one ends, I always suffer a post-project dip. I spend so much time and energy successfully delivering a tech project that when it’s over, my brain and body don’t know what to do. I often have to dig deep into my energy reserves to get the project over the finish line. Once the project is over, my body crashes. I used to ignore the drop in my energy levels, occasionally wondering why I was so tired and distracted and unable to clearly focus on the simplest of tasks. I experienced the same thing when I trained for half marathons in my early forties. The months of training, and the race itself, took their toll on me.

Eventually, I realized what was going on and built recovery time into my schedule for both projects and races. During this recovery time, I was kinder and gentler with myself. I also conducted what I called mini and informal postmortems. I looked back on the project or the race and mentally noted what went well and what could have been better.

When I took the time to do this, I cruised through the dips. Reenergizing for the next thing became simple. When I didn’t have the mini and informal postmortem, my energy lagged. I felt as if something was missing. Yep — sure was. Closure. In hindsight, I should have done this after each birthday, after each of my kids’ birthdays, after we moved, and any other time that there was an ending.

We are terrible at endings, and this is not a good thing.

My executive coach, Bev, has talked to me for years about the importance of closure. She says, “We need to take the time to reflect on an activity, project, job, or phase in our life.” It’s true. We often blow through these things, and I guarantee we suffer as a result.

The writings of a guy named Richard Davis, commenting on how his granddaughter was turning thirteen and would be having her Bat Mitzvah, caught my eye. The celebration honored the end of her childhood and the beginning of adulthood in her community. While I’m not particularly religious, I appreciate religious traditions that allow for the honoring of endings and celebration of beginnings.

What struck me was the following:
“We so often dread endings. This may be because we build our lives around what is familiar, and we are frightened by change. When something ends, the things that used to be familiar might become rare or even strange. We might have to change, and that can be the most difficult task of all. Yet, as we have all heard, the only constant is change. If we can learn to think of a time of ending as a time of a new beginning, we might relax, at least a little. Beginnings are often the most rewarding times, for it is often there that growth begins. Each season has an ending leading to the beginning of the next. And out of that constant change comes rest, growth, and life.”

I love this. It reframes where we are in midlife when we think so much is behind us or is ending. We may have kids heading off to college. We may lose a loved one. We might not get the same appreciative looks when we walk into a room. We may get laid off from a job that we love. All of this can feel like overwhelming loss … but, if we reframe our view to look at what is ahead, and let go of what is comfortable, we can create something perfectly suited to our specific needs and desires.

Our journey is our own game of Life (literally and figuratively). We get to make choices as we move to the next space on a board of our own creation. This game of Life comes with our own rules and players. We can choose to pause, take a few steps back, move sideways, or accelerate through the spaces, all at different points in our lives.

It is our journey, after all.

ALL THE PIECES COME TOGETHER

Each woman is unique in the opportunities available to her and the experiences she’s assembled over time, but ultimately all of this comes together to form our own personal mosaic, each beautiful and rich in its own way.

Amy, an entrepreneur from the northwest, said, “Everyone’s journey is their own. Each individual will need to take inventory of their elements and ingredients and how they mesh with their own comfort level, desire, and DNA to design and craft their own journey.”

The idea that the pieces of our lives come together to create a piece of art like a tiled mosaic, a stained-glass window, or a tapestry is a striking one that I love. Personally, I am aiming for one hell of a tapestry that rivals the Bayeux Tapestry in Normandy, France.

One of my favorite lines from the movie The Best Exotic Marigold Hotel says, “Everything will be alright in the end. If it’s not all right, then it’s not yet the end.”

This is magical and liberating. It means that we don’t have to have it all figured out at the start. We can figure it out as we go. We can be optimistic knowing it will all come together just as it should.

This is important. As we are creating and assembling the pieces of our lives, it’s difficult to see the bigger picture. We can take a step back to try to get a broader view, but even then, we don’t necessarily have all the pieces or the right vantage point. We must have faith in the process and that we are doing our best possible work.

I think about when I decided to write a book in 2016. I had the suggestion of a process and then a topic and a title. In a few weeks, I’d created what I thought was good enough content, shared it with a friend, and ended up completely derailed. I stalled out until I heard a podcast two years later and had more experience as a woman in my forties. Only then did all the pieces come together to create this book.

My friend and fellow author, Connie, said, “At some point, we are able to look back and piece together the path. Until that point, it may not make sense.”

It’s a good reminder, because eventually it does make sense. Eventually, it all comes together.

IT’S WORTH THE EFFORT

When I interviewed Georgia for this book, she spoke about a venture she’s been struggling with for years. “I’ve had to work hard and have chosen to make sacrifices,” she said. “Through it all, though, it has been worthwhile. It’s been worth all of the effort.When everything seems to be falling apart, I press on. I’ve learned to ask for help and share the journey so that I can get out of my crazy brain. With each win, I’ve gained the confidence to keep moving toward my vision. I will succeed.”

It took (and takes) courage for not only Georgia, but for all of us, to press on when the going gets tough or we are uncomfortable or scared. We have to have faith in ourselves, knowing that we are worth the effort. Our lives matter. Our choices matter. And we can be afraid and still go for it.

We may need to be courageous to get to confidence. This pretty much sums up the way we need to approach this journey.

Be courageous, and know it’s worth the effort.

TAKING THE CONTROLS
— Am I the top priority in my life?

— What am I looking forward to?

— What are my anchors as I transition through midlife?

About the Author

Terri Hanson Mead is an entrepreneur, angel investor, startup advisor, expert witness, podcaster, YouTuber, writer, mother, wife, and commercially-rated helicopter pilot based in the San Francisco Bay Area. She is passionate about encouraging ALL women to live their best lives, especially those over the age of forty.

Want More?

To read the rest of the book (or listen to it), order on Amazon (ebook, paperback, audiobook narrated by Terri). For other purchasing options, go to the Piloting Your Life website.

Not Ready to Buy but Still Want More?

For more from the book, watch Terri read On Botox, one of the Flight Diversion sections in the book.

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Terri Hanson Mead
Terri Hanson Mead

Tiara wearing, champagne drinking troublemaker, making the world a better place for women. Award winning author of Piloting Your Life.