4 Tips for 40/50-Year-Old Lawyers to Reignite Their Freedom

An Ironic Celebration

There’s a profound irony in celebrating July 4th here in the United States.

Americans love to spend the day grilling food and blowing shit up to celebrate our country’s independence from England. This is the one day where the gusto with which Americans love to shout “freeeeeedom” is rivaled only by the scene in Braveheart where Mel Gibson is about to meet his maker and yells, “freeeeedoooom” as his dying word.

The day after July 4th (often hungover and tired from staying up too late watching the bombs bursting in air) we wake up and before our feet even hit the ground for our morning constitutional and coffee, we unconsciously slap on a pair of golden handcuffs that symbolize anything but freedom.

On one hand, these golden-handcuffs — from an an external perspective — allow many Americans to have privileged lifestyles that afford various kinds of freedom.

On the other hand, these golden handcuffs have left many of us feeling anything but “free” from an internal perspective.

Thus, here’s the irony of celebrating the 4th of July: the freedom we externally celebrate and experience on that one day out of the year, often isn’t experienced internally in the remaining 364 days of the year.

For 23 years as a lawyer, the golden handcuffs of the legal profession gave me so many privileges of freedom, and simultaneously created a sense of internal imprisonment. It wasn’t until I was about 45 that I started feeling the pinch of these golden handcuffs in my life, and the associated internal imprisonment.

The Opposite of Freedom as a 40/50-Year-Old Lawyer

I know I’m not alone. Most of my friends are lawyers. I worked with lawyers and other legal professionals for 23 years. And I have many lawyers as current clients.

And the common denominator — especially among lawyers who’ve reached their 40’s and 50's — is a growing sense of feeling trapped. That “trappedness” then leads to a host of other feelings, like restlessness, lostness, and hopelessness.

It makes total sense: we’ve spent the first half of our lives building up our career and everything that is “supposed” to go along with that. The house. The car(s). The family or living on your own. The vacations. Maybe even the vacation homes. The debt . . . all the freaking debt . . . from mortgages, to credit cards, to student loan debt. Kids’ schools. Taking care of aging parents. Saving for retirement. Buying all the “stuff” that we believe buys us “freedom.”

By the time we reach our 40’s and 50’s we’re wearing so many pairs of golden handcuffs that it’s a wonder we can raise our hands to sip a glass of wine at nite to numb ourselves.

And what’s even more ironic (or maybe it’s hypocritical), is that this lost sense of freedom clashes with the wild and rebellious freedom that so many children of the 70’s and 80's — the forgotten GenX’ers — grew up experiencing.

We spent the first 18 years being wild and free, roaming the streets by ourselves, taking care of ourselves at home alone until our parents came home (shoutout to the latchkey kids), and basically doing whatever the hell we wanted to do (because we actually knew the difference between what to do and what not to do).

Then, once we went off to college, the trappings of American life and what it means to be “free” started slowly sucking all of that natural freedom out of us.

Now we’re in our 40’s and 50’s wondering what the hell happened to ourselves. Especially if you’re an overachieving, Type A, box-checking lawyer like me.

So, what can we do?

Over the last few years, I’ve found 4 practices that have been helpful to reignite that sense of true, natural freedom.

The first two are practices that you can do all day, every day, in any moment . . that can help you change your relationship to the golden handcuffs you’re wearing, even if you feel like you can’t get them off right now.

The second two take a little more effort and intention . . . and maybe, just maybe, could either allow you to unlock those golden handcuffs or at least find some temporary relief from them.

4 Tips to Reignite Your Freedom

First: Recognize Your Sense of Lost Freedom

In all the work that I do with my clients, the first step is always, always awareness.

We can’t begin to address what we’re unwilling to acknowledge.

The 40- and 50-year-olds out there are part of Generation X: folks whose perspectives where shaped by certain events and experiences during our childhood years in the 70’s and 80’s.

Raised in the 70’s and 80’s, most GenX’ers were taught to “suck it up,” “stop whining,” “just look around and somebody’s got it worse than you.”

And that’s a mentality that most of hold wear like a badge of honor now in adulthood.

But here’s the thing: even if you think that mentality has worked for you, let me invite you into another perspective.

What if that kind of “suck it up” mentality doesn’t work as well as you thought it did?

The invitation here is to open up to at least recognizing and acknowledging that something inside you feels trapped . . . that something inside you yearns for more freedom.

Yes, maybe you’re not as trapped as someone else you know . . . but, so what?

The road of comparison is paved with suffering.

Can you at least start to become aware of the ways in which you feel like you’ve lost your sense of freedom?

What does that feel like for you?

Where in your body do you notice a longing for more freedom?

What might that longing for more freedom be trying to tell you?

See, here’s the real pisser: that sense of lost freedom doesn’t go away by ignoring it. Like a pebble in your shoe on a long hike that you ignore, it just starts to irritate you and rub a nasty blister.

So, let’s start to reignite that sense of freedom by at least acknowledging that we feel like we’ve lost some of it.

Second: Bring in Mindfulness and Self-Compassion

I’m talking here about ancient, spiritual practices of mindfulness and self-compassion. Not quick hacks or cute little memes about “be more present” or “love yourself.” Yeah that’s all great — but they miss the deeper meaning.

By “mindfulness” I mean (a) becoming aware that you feel like you’ve lost some of your freedom (which you already did in step 1, so good job) and (b) trying not to judge or resist that sense of lost freedom.

Then, to help us try not to judge or resist that sense of lost freedom, we can bring in self-compassion.

Here’s another irony: self-compassion in Eastern Buddhist traditions is basically a no-brainer. It’s where everything starts. For Westerners, and particularly Americans who have been socialized to believe that kindness is weakness, self-compassion can feel . . . well, pretty damn challenging and about as natural as an 80’s perm.

So, please — never, ever force yourself to feel kindness or love or compassion for yourself. Instead, crack the door open a little bit. Allow self-compassion to gently seep in like tiny hints of fresh air.

Start by saying something to yourself like “this sucks.” “I’m feeling bad in this moment.” “This hurts.” This allows you to acknowledge the impact and experience of this sense of lost freedom.

Then, treat yourself like you’d treat a good friend who was in pain. Say some kind, comforting things to yourself. Or, if that feels “weird,” imagine someone else saying kind, comforting things to you.

The point of self-compassion is not to make yourself feel better or make the sense of lost freedom go away. To the extent that there’s a “point” (an antithetical notion to mindfulness practices), it’s to show some kindness to someone who is in pain simply because they’re a human being. And that human being, my dear, is you.

Yes, you deserve to be shown some kindness and compassion for the lost sense of freedom you’re experiencing.

Third: Get Crystal Clear on What’s Most Important

And by “most important,” I mean your Core Values.

When we’re feeling lost, restless, or trapped, these are all good signs that we’ve gotten disconnected from what really matters to us.

It’s like we’ve ended up wandering along in a dense forest with no compass, just hoping that we’ll eventually find our way out before we start hearing banjos play.

To do that, we need to cultivate what I call our Inner Compass. Cultivating our Inner Compass is deep work — it’s not quick or easy. Yet, it’s so crucial.

Back when I was really in the depths of depression and anxiety because of my golden lawyer handcuffs, I took some time (3 days actually) to figure out my Core Values . . . something I’d never done before.

That was almost 7 years ago. And those Core Values are tattooed on my heart and soul. They are not only what guided me out of the dark forest, but they are what keep inviting me to unlock the golden handcuffs that I still unconsciously wear.

Here’s a quick process to start cultivating your Inner Compass:

Spend some time writing out your list of 3–5 Core Values.

Then, reflect on what those Core Values mean to you. How do you define them?

Next, start with just one of those Core Values and consider what gets in the way of you honoring that Value more consistently.

Finally, write down one small step that you can take to start to honor that Core Value more.

By the way, this Inner Compass work is the bread ‘n butter of what I do with my clients. So if you want some deeper support around cultivating your Inner Compass, I’d love to chat with you.

Fourth: Make a Small Change

When I say “small change,” I mean that and only that.

No way in hell am I advocating for anyone to ditch their lawyer job, leave their family, or skip town and go off-grid. I recognize that everyone has their own unique circumstances . . . their own particular facts of life.

And while we want to reignite that sense of freedom in ourselves, we don’t want to do so at the expense of other people in our lives or the particular facts of our situations.

So, when I say “small change,” please accept the invitation to not go overboard or leap off a cliff.

What’s one small thing that you would love to do, but haven’t given yourself permission to do?

What’s something that you always wanted to do as a kid, but never got the chance to do? Or that maybe you used to love as a kid, but haven’t done in a long time?

What’s something you always thought you’d do, but never got around to doing?

Notice what happens in your body as you imagine these things. Pay attention to those sensations . . . those stirrings.

There’s wisdom in those stirrings.

One way that I started to introduce small change in my life even before I knew that I wanted to quit being a lawyer, was by keeping a “Things That Bring Me Joy” list on the “Notes” app on my iPhone.

Sounds silly, but trust me, it was profound.

I wrote down every thing I noticed that brought me even the slightest bit of joy.

Like snuggling with my dog.

Hiking.

Listening to the birds sing.

Helping people.

Whatever it was, it went on the list.

And over time, I started seeing patterns in that list. Stirrings. Whispers of what I wanted more of in my life that allowed me to feel free, even when I felt trapped in the golden handcuffs of my career.

Eventually that list showed me that my true freedom did lie in quitting my lawyer job and starting my own business as a coach and mindfulness teacher who could help people.

But even before that, I was able to introduce more of those joyful things in my life on a daily basis.

And those tiny changes of bringing more joy into my life, started to reignite my sense of freedom.

What’s One Tip You Want to Try?

Reigniting your freedom isn’t something that happens overnite. There’s no hack. No quick fix.

And . . . it is possible to get a little spark going.

So, this July 4th, my invitation is for you to ignite a more powerful spark than a firecracker.

Because the fireworks on July 4th that are supposed to celebrate our freedom are only fleeting.

Reigniting the freedom within you that you can carry into the rest of year, is a more sustainable celebration of freedom.

Which tip are you going to try first?