Late for the Sky, the heartbreakingly plaintiff and personal song by Jackson Browne, “[is] about a moment when you realize that something has changed, it’s over, and you’re late for wherever you’re going to be next.” Are you feeling late for the sky in your next Act, your Third Act of Life — retirement?

The question is inspired by a confluence of questions and experiences in our lives.

A revelatory night with Jackson Browne

One experience? A happy and fortunate twist of fate. Business travel brought us near the state capital. I checked to see what shows were playing. Two late, last-minute tickets were available. The last pair of side-by-side tickets in the cheap seats. Potluck, the venue would assign us the best seats left. We thought, what the heck. Enjoy the music from the back of the house. We could close our eyes and wish with all our might.

Instead, the tickets materialized as front-row tickets to one of our musical idols, Jackson Browne. It was like a concert in our living room, only with some 2,000 people behind us. Perfect sound. Masterful artists. Three hours of thundering piano, driving guitars, and soul-baring harmonies. I wore out several Jackson Browne vinyl albums and CDs listening to inspired turns of the phrase and singing along to soaring lyrics. Hold Out was the concert I couldn’t afford in college but desperately wanted to attend. This concert was everything dreamed of and more. And the words came flooding back.

Late for the Sky stood out. Like a signpost of life, for the Third Act of Life.

third act of life

Front-row tickets to one of our musical idols, Jackson Browne.

Over the Threshold

Simultaneously, we’re debating the exact timing of retirement. I’ve crossed one of those magic threshold numbers at 59 ½.

Now those retirement savings plans are accessible. The numbers work. Or can be made to work. Retirement is a financially viable option.

But interesting and challenging work opportunities keep proliferating, the product of a persistent career of failures, results, and networking. Yep, failures teach us too. The opportunities can be both exciting and oppressive. Can’t do them all. Must be selective. Are the opportunities mission and purpose? My mission or purpose? Or someone else’s? Do the work projects pull me away from what’s important and possible? Is it time for breaking away? Choosing that Third Act of Life?

I know that many retirees miss the identity of their former work. The loss of authority or acknowledged expertise can hurt. The rewards of work are not all financial. The emotional and intellectual rewards are often just as important. Can I find those rewards in my Third Act of Life over the retirement horizon?

The closer I get to reality? The more apparent it becomes that uncertainty discounts future options. Work too long in life and the random health crisis might preclude your plans for travel and adventures as a couple. Quit too early or on the eve of a market correction? And the numbers don’t work as well. There’s no perfect answer. The future is unknowable with any degree of certainty. Get used to uncertainty. Taking the leap is ultimately a flier — an act of faith.

The Snake Oil of the Second-Act Industry

Then we read an article in The New York Times on the Second-Act Industry and workers struggling to stay productive and relevant in mid to late-career. Degrees, certificates, coaches all promising a brighter future, a better you. All for the low, low price of thousands of dollars.

Do we need the stamps of approval or dictates of experts to change?

Truth? We share the vision of a positive life experience through the changes of aging. That is the central story of Aging with Freedom. We’re pursuing our trifecta of High Wealth, High Health, High Purpose.

But we’re not selling snake oil nor handing out red pills. We’re advocating for do-it-yourself (DIY) building of a Third Act. A successful, happy retirement is a choice, or more accurately a habit of choices. Happiness, health, purpose are things you can’t buy. High Wealth or financial security can and does improve your freedom of choice. High health gives you the freedom to enjoy the choices. Wealth and health are functions of our choices, but the randomness of chaos also has a say. And happiness still requires High Purpose or serving something beyond self and idle leisure.

The mid to late-life career change challenge begs the question? Sprint to the end of a career? Keep striving for the money – The Pretender’s “legal tender?”

Or choose wherever I’m going to be next, rather than waiting for some life event or health crisis to choose for me? Maybe adjust expectations and spending? Say by geoarbitrage or downsizing?

One lesson from the Times? Making the choice shouldn’t cost thousands of dollars.

How Long Have I Been Sleeping

Has something changed in me? In my relationships? Is it time to move on? One issue for us? Retirement is a couple decision. It may be my career. But that career is inside a larger relationship with my spouse. She’s more than ready for that next, Third Act of Life. The road is calling out, promising new adventures together. Before it’s too late. Time for me to wake-up?

How long have I been sleeping

How long have I been drifting alone through the night

How long have I been running for that morning flight

Through the whispered promises and the changing light

Of the bed where we both lie

Late for the sky

Time for Third Act of Life — Time to Fly

Is your Third Act of Life calling? What is the exact right time to start retirement? Maybe, you already answered the call and choose retirement or post-employment entrepreneurship? How did you make the jump?

We drift along sometimes in life. Doing what we’ve always done. Go to work each day and struggle for the legal tender. Are we at that inflection point where it’s time to choose that something different? Are we late for wherever we’re going next? That Third Act is calling. Late for the sky.

Curious about how you may have reached the decision to fly.

Care to share?