What Amy Winehouse Taught Me About Turning 27

Every time August comes around, I have that “Woah, my birthday is soon,” realization. This year, the “Woah” wasn’t like the ones that preceded my 16th or 20th. This one, coming before my 27th, hit more like, “Oh.”

How boring a number it is, 27.

Initially, I attempted to find reasons it was special. Things like:

  • 27 is the official start to my late twenties
  • The last time my birthday was on a Friday, it was my 21st

I was like a sports reporter with interesting statistics that predict nothing. I eventually dropped it.

A week into August, I visited an Amy Winehouse exhibit curated by her brother Alex. In his introductory wall text, he writes,

“This is not a shrine or a memorial to someone who has died. […] Babies are born, people get married, they get old (should they live so long), and then they die. […] This is a snapshot of a girl who was, to her deepest core, simply a little Jewish kid from North London with big talent.”

Alex wants us to accept that during her time in this world, though unconventionally short, his sister lived, loved, and struggled, as we all do in some way, at some point, for some length of time.

Amy was 27 when she died.

The text reminded me of my earlier quest to make some random number special. It encouraged me to consider that perhaps no age, no time in our lives, is objectively meaningful.

The timeframes we create for ourselves are mostly arbitrary. They are random units of time to which we attach meaning. Aside from being permitted to operate a vehicle, buy cigarettes or drink alcohol, nothing happens only because you’re a year older.

Who we are – and who we wish to be – transcends the boundaries of time.

Looking back, twenty-six was just another year. In fact, there were several moments when time itself had no meaning. Three stand out above the rest.

3 Times Time Meant Nothing During My Past Year On Earth

1. When my dog lived three bonus years

Pepper in her pre-bonus years

Three weeks after I turned twenty-six, my dog Pepper died. The loss was like nothing I’ve previously experienced. I’m still empty.

As I left the animal clinic for the last time, her vet offered his silver-lined condolences. “It was purely old age. You should feel lucky you had three bonus years.” When she died at age fifteen, Pepper had lived three years past her life expectancy. Though my vet’s comment was meant to ease the pain, I was unable to appreciate it.

I am grateful for the time I had with Pepper, and despite enjoying three years more with her than science predicted, I will never feel that it was enough. I long to spend more time with her. If not another fifteen years, fifteen minutes. Or fifteen seconds.

Though at some level we know that everyone and most everything in our lives are impermanent, they quickly become part of us in ways we rely on. We hope they never leave us, but if and when they do, we can’t help but wish we could have had more time.

There is no solution to this temporal struggle, except perhaps to accept that we will never be satisfied with the time we are given. We can remind ourselves to appreciate the small moments, knowing full well that we will frequently forget and take them for granted. Time will never be enough.

2. When I didn’t freeze my eggs

Last October, my plans to sleep through a ten-hour flight from London to San Francisco were thwarted by a chatty neighbor. She was forty, dating, and her prospects were dismal. What about me? Did I have a boyfriend (“A sweet thing like you, you must!”)? And if not, what was the dating scene like (“Especially for someone your age!”)?

Learning that I did not have a boyfriend silenced her for the first time, but only momentarily. Her pupils pierced mine as she brought her seat upright.

“Now listen to me. If there is one thing I wish someone had told me when I was your age, it’s to freeze your eggs. You just have to. Twenty-six, no boyfriend. It’s the only way.”

I thanked her for the advice.

For the rest of the flight, I alternated between indignation and anxiety. Was time running out? Was she right?

Once back on the ground where altitude and air pressure are more conducive to rational thought, I unpacked our conversation. Several sleepless nights, discussions with friends, and science articles later, I concluded that the lady’s advice was, literally, for her at my age. Between wanderlust, graduate school and a career ladder, she deliberately postponed her plans to have a family. “I went to business school, traveled for a few years, then got job and wanted to be quickly promoted. I didn’t have time. But I also wasn’t interested in having a family then.”

She and I are different people and her late twenties and thirties were starkly opposed to what I can imagine for mine. No, her advice was not for me at my age.

Time is our constant. It’s what connects us. A year for me is a year for you. But no two people will fill a year, or all our years, in the same way. Though we may share experiences at the same time or have the same experience at different times, there is no objectively right or wrong time for anything (though there are better and worse times, as in this case). There is time, and then there is time for each of us. To attempt to cut and paste others’ time onto our own is pointless. Time exists objectively, but it is relative in the context of our lives.

3. When “later” became now

March 10, 2010

I first applied to IDEO as a college junior, in search of an internship. The company’s approach, values, and ethos resonated with me at a deep level. It fit.

“I’m holding out,” I wrote to a friend as we exchanged summer plans. “It could take up to four weeks for me to hear back from them.” When I didn’t hear back by the time summer started, I took what was the next best opportunity for me at the time. Fall of my senior year, I tried again, this time in the hopes of landing my first full-time position. In January, I received the following email:

thank you for your interest in IDEO.
we don’t really hire new grads. We typically require a greater depth of experience.
I wish you the best of luck with your job search.

We weren’t wrong for each other. The timing was wrong for both of us. “Maybe later then,” I told myself. The post-graduate role I did receive made me the person I am today, both in the skills I learned and the people I met. Ready for a new endeavor three years later, I considered applying again to IDEO, but decided the time wasn’t right for me. I knew it eventually would be, but at that point, startup-life called.

My third application to IDEO came five years after my first. “This is it,” I told myself. I was ready to wait it out as long as it took. “Are you looking at anything else?” A friend asked. “I’m holding out,” I said. I wasn’t seriously looking for a new job anyway.

Eight months later, I entered IDEO’s San Francisco studio as an employee.

Golden Gate Park, San Francisco

Much of our day-to-day lives are calendared. We have little control over many of those agenda items. Rent will be due whether or not we want to pay it; trains will leave whether or not we’ve boarded them.

Our adherence to short-term schedules makes it tempting to think about our long-term in the same way. “She wants to be married by twenty-seven,” I recently heard. “If I’m not promoted by next quarter I’ll leave my company,” someone else told me.

The problem is that we can’t force arbitrary timelines. If the right partner or opportunity hasn’t come along by the time your deadline does, will you drop your standards or give up? If some unexpected path proves to be superior by the time you hit your deadline, will you ignore it? We need to let things play out. Deadlines are dead-ends.

My path to IDEO helped me see how, instead of focusing on the timing that feels best, we’re better off focusing on the outcome that feels best. We can then design and redesign our paths toward those outcomes. Notably, this does not mean sitting and waiting. It means zigging and zagging and accepting that some zag may become your main path. Arbitrary timelines force us to make myopic tradeoffs and lose sight of the big picture. Trade your timelines for lifelines.


While 27 as a number may not serve any special role except perhaps for departing flights and the 9 and 3 times tables, I’m poised to pour my own meaning into it. To invent what will make it special for me. When the time is right for you, take your years and do the same.



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