The Ambition Edit

On ambition, the corporate ladder, and realizing that the next chapter of a good life doesn't necessarily have to be bigger.

There's a jigsaw puzzle I'd like to finish, a stack of books I keep meaning to read, and a few creative projects waiting for a quiet afternoon.

None of them is particularly urgent. Which is probably why they keep getting pushed aside.

Somewhere between work, the things that need doing around the house, family responsibilities, and trying to fit in a little exercise, another day disappears. Sometimes an entire weekend.

It's a peculiar thing to realize that you've worked for decades to build a comfortable life, only to find yourself wishing you had more time to enjoy the ordinary parts of it.

I have a good life. I know that. I've been fortunate to earn enough to pay the bills, save for the future, and occasionally buy something beautiful without having to justify it. My career has taken me places, introduced me to interesting people, and given me work that I genuinely care about.

But lately, I've been thinking about something I never gave much consideration when I was younger.

What if the next step isn't up?

The Ladder I Thought I Was Climbing

I was given my first director role at 29.

At that age, I didn't think much about what it meant for the rest of my career. I was doing work I enjoyed, being recognized for it, and naturally assumed that if I continued working hard and doing a good job, more opportunities would follow.

And for a long time, they did.

I came of age professionally when the path seemed fairly straightforward. You worked hard, learned your business, took on more responsibility, and eventually moved into bigger roles. The title changed, the salary grew, and you kept climbing.

There wasn't an entire internet full of people building businesses from their kitchen tables or documenting their lives while earning a living. Most of us couldn’t imagine a world of careers as content creators or independent entrepreneurs.

We were building careers inside organizations. And the ladder was supposed to lead somewhere.

I still believe in working hard. I still believe in being good at what you do.

What I no longer believe is that the relationship between effort and advancement is quite as simple as I once thought.

Over the years, I've watched opportunities become more complicated. People stay in positions longer. Entire layers of management disappear. Organizations change direction, sometimes before anyone has had a chance to settle into the last change.

And being good at your job doesn't necessarily mean you're the person who gets the next opportunity.

That's been an adjustment for someone who spent much of her career believing that good work would speak for itself.

I don't think organizations are uniquely flawed. They're made up of people, with all the personalities, loyalties, and competing priorities that come with them.

Still, it's an odd realization after spending so many years believing the rules were different.

When More Stops Feeling Like More

The higher you go, the more complicated the trade-offs can become.

There are experiences I wouldn't exchange for anything. I've traveled, met remarkable people, contributed to work that matters, and developed friendships with colleagues who have become an important part of my life.

Those experiences are among the things I value most about my career.

But somewhere along the way, I began to notice that I was enjoying those parts of my work more than the machinery surrounding them.

The meetings. The reorganizations. The constant pressure to do more with less.

Technology has made so much possible, including the ability to work from almost anywhere. Yet somehow, for many of us, it has also made it harder to be entirely away from work.

The workday follows us into the evening. A Sunday afternoon becomes an opportunity to get ahead on Monday. A weekend away doesn't always mean the laptop stays closed.

I remember when unlimited vacation time sounded like freedom.

Now I find myself thinking that the real luxury isn't necessarily having more days available to take.

It's feeling that those days, and the hours surrounding them, actually belong to you.

I haven't stopped wanting meaningful work.

I've simply begun questioning how much of my life I'm willing to organize around it.

The Life That Doesn't Fit Into a Career Plan

Of course, deciding that you want more freedom and creating a life that allows for it are two different things.

My husband and I live in a beautiful corner of Cape Cod. It's the kind of place people travel to for their vacations, and there are still moments when I look around and feel extraordinarily lucky to call it home.

But living somewhere beautiful doesn't make the practical realities disappear.

The Cape has become increasingly expensive. Many of our friends and family have moved elsewhere. And we're at that stage of life when our own plans have to be considered alongside the needs of family members at different stages of life.

My in-laws are in their eighties, and being nearby matters.

So while I sometimes imagine what it would be like to live somewhere new, with a little more flexibility and perhaps a different pace, we're not making those decisions in isolation.

I suspect a lot of women my age understand this particular in-between place.

We're thinking about retirement while still very much working. We're making plans for the years ahead while helping the generation before us or after us navigate theirs. We're beginning to ask what we want from the second half of life, often while everyone else still needs something from us.

It's not quite the carefree reinvention story we're sometimes sold.

There are mortgages and healthcare and retirement savings to consider. There are people we love and responsibilities we wouldn't dream of abandoning.

There is a great deal to be grateful for.

And sometimes, a great deal to carry.

A Different Kind of Ambition

What surprises me is that I don't really want to stop working.

I want to work differently.

I still love the field I've spent so many years in. I love helping organizations think through difficult problems, preparing leaders for the unexpected, and bringing people together around work that matters.

I've also been thinking about ways to bring my professional experience together with something much more personal: my love of rescue animals. And volunteering in my community more.

It's a different sort of ambition from the one I had at 29.

I'm less interested in how impressive a title sounds and more interested in whether the work is worthwhile, whether I enjoy the people I'm doing it with, and whether there's room for a life outside of it.

I'd still like to travel for work. I enjoy meeting people, exchanging ideas, and being part of a professional community.

I enjoy the conversations and connections that happen in person. What I don't enjoy is spending hours commuting to an office when the work itself could just as easily be done elsewhere.

And I don't want to reach the end of another busy year wondering where all the ordinary days went.

The Things That Make a Life

Lately, I've been making a more conscious effort to say yes to the things that are easy to postpone.

Dinner with old friends on a Monday night. A conversation with someone I enjoy. An afternoon spent doing something with no particular purpose beyond the pleasure of it.

I've taken an interest in decoupage. I've rediscovered how satisfying a jigsaw puzzle can be. There are books I want to read simply because I'm curious about the subjects, not because they'll help me become better at my job.

And there is my husband, my favorite person, with whom I'd like to spend more unhurried time.

None of these things looks particularly impressive on paper.

They don't belong on a résumé. They won't lead to a promotion. There isn't much to measure.

Perhaps that's part of their appeal.

For most of my adult life, I've been accustomed to thinking in terms of accomplishments. What needs to get done? What's next? What could I be doing better?

It's a useful way to approach a career.

I'm beginning to wonder whether it's such a useful way to approach an entire life.

Because even the things we love can become another list of things to accomplish.

Exercise. Read more. Make something. See friends. Spend time outdoors. Travel. Cook a new recipe. Learn something new.

Before long, even leisure starts to feel like a calendar that needs managing.

I'm trying to resist that.

Maybe I don't need to finish the puzzle this weekend. Maybe reading a few pages is enough. Maybe a walk with my husband doesn't have to count toward a fitness goal to be worth taking.

I want to get better at enjoying things without immediately thinking about what comes next.

Enough, for Now

I haven't figured out exactly what this next chapter will look like.

I still have professional goals. I still have financial goals, and I know that the freedom I'm imagining will require thoughtful decisions rather than one dramatic leap.

There are things I want to build, places I want to see, and contributions I still hope to make.

I don't think I'm becoming less ambitious.

I think I'm becoming more particular about where I put that ambition.

At 29, success looked like another opportunity, a bigger role, the next rung on the ladder.

At this age, it looks a little different.

It looks like meaningful work that leaves room for the rest of my life. Enough financial security to make choices rather than simply meet obligations. Time with people I love, a little space to be curious, and the freedom to occasionally spend an afternoon doing absolutely nothing productive.

I still want to do good work. I still want to grow.

But I don't want to spend the next decade working toward a life I never quite make time to live.

Perhaps enough isn't a number or a title or a point we eventually reach.

Perhaps it's recognizing that some of what we've been working toward is already here.

And making a little more room to enjoy it.

Warmly,

Ashley