‘I feel stuck’: How to embrace ‘wintering’ when your ambition is tapped

Feeling less than inspired at work? Here’s how to embrace “wintering.”
Illustration by Anna Parini

This is the second in a series of stories on how we are reframing ambition in 2023. What does ambition mean to you? Email senior writer Alicia Adamczyk for a future article. 

Ali Vingiano felt an internal light switch off sometime over the past three years. Like so many, the TV writer, creator, and newsletter author was dealt a difficult hand throughout COVID-19: She uprooted her life to care for a sick relative, her scripts weren’t selling, her dog died.

She felt weighed down and angry about her situation. Though she is emerging from it now, Vingiano has been stuck in what she calls a down cycle: “A period of perceived failure, of feeling lost, of not knowing what’s next in my career for the first time in my life,” she wrote in her personal newsletter in the fall of last year.

“Nothing feels like passion, ease, arrival,” she wrote. “I feel stuck. I grasp at the memory of daily creative flow. I wonder why I can’t do more, be more, make more.”

While those are uncomfortable feelings, Vingiano has found solace in accepting them; doing so has allowed her to cultivate self-compassion and gratitude. She’s mad. She’s creatively unfulfilled. But she also knows that it’s all temporary—she’s been through this before.

Vingiano’s last down cycle came just before her biggest career achievement to date, landing a writing role on the Apple TV+ hit The Morning Show. That experience taught her it’s better to embrace the ebbs when they come, and flow when you can. 

“A down cycle, it’s just inevitable. That’s how life is. No one has ever just had a great time for 100 years and then died. We all have hard times,” Vingiano tells Fortune.

Though we think of life as linear, it isn’t. There are seasons to stay attuned to; no one rides a wave higher and higher forever. Winter is always around the corner.

Wintering is a ‘a time for reflection and recuperation’

Author Katherine May refers to the down cycle Vingiano experienced as “wintering.” In her book on the subject, May describes wintering as a “fallow period in life when you’re cut off from the world, feeling rejected, sidelined, blocked from progress, or cast into the role of an outsider.” 

Those are feelings likely familiar to many of us as we continue to negotiate what our lives look like after COVID-19. Conversations about languishing, about burnout, about a lack of ambition abound as we work out who we’ve become and what we want moving forward after the past three years of turmoil and trauma, of our collective winter.

But wintering is not simply a dead season; it’s just as important in the natural world as it is to the human spirit, May writes. When times are difficult—you don’t know what you’re doing, or you’re feeling resentment or an overall lack of ambition—it’s best to listen to your instincts and slow down; allow yourself to rest and retreat. 

“Once we stop wishing it were summer, winter can be a glorious season in which the world takes on a sparse beauty,” May writes. “It’s a time for reflection and recuperation, for slow replenishment, for putting your house in order.”

In our productivity-obsessed society, “the times when we fall out of sync with everyday life are still taboo,” May writes. We see wintering as a “humiliation,” to be avoided at all costs, lest we be seen as lacking willpower. But wintering is natural. It “brings about some of the most profound and insightful moments of our human experience.” Rather than deferring it all costs, we’d do better to “invite the winter in.”

Applied to making art or even to work in a corporate setting, wintering can be a useful concept. Though it goes against our culture’s workaholic norms, sometimes the best thing you can do is settle in and take your time before jumping to the next project. Inherent is the idea that it is temporary: Spring will follow. Like Vingiano, our most fruitful season could be nearing, if only we’d allow ourselves the time to regenerate.

“This is life,” says Vingiano. “I will go through incredible periods of abundance and happiness, and I will go through incredible difficulties where I’m changing and growing and faced with new complications, faced with things I’ve never dealt with before. And then I’ll go through another cycle of abundance and happiness and peace.”

For those who can’t unplug, small steps help

Of course, only the most privileged among us can afford to take some time to properly rest. The rest of us need to work, and work hard, all the time to survive. It’s one thing to practice self-compassion and gratitude, and another to unplug and recalibrate completely.

Still, as Satya Doyle Byock, a psychotherapist based in Portland, Ore., and author of Quarterlife: The Search for Self in Early Adulthood, previously told Fortune, resting doesn’t have to mean quitting your job and embarking on your own version of Eat Pray Love. There are plenty of simpler, more accessible ways to inhabit your winter season, to dig into your down cycle.

For Byock, listening becomes paramount in down times. Pay attention to what is calling to you in these moments: What seemingly irrational curiosities do you have? What keeps you up at night? Whose work instills interest and excitement? All of this is information that can guide you in the direction you ultimately want your life to go.

One of the most profound changes Vingiano instituted was actually fairly small: She started meditating each day for a few minutes when she woke up. But cultivating tiny habits makes a big difference. And if you can turn them into a routine, then you will be continually showing up for yourself. 

“If you can find a goal to stick to, it teaches you how to trust yourself,” says Vingiano. “Make small shifts in your day to day life that aren’t focused on work, but are focused on getting you to a place where you can feel good about yourself, be kind to yourself, and able to access inspiration and creativity.”

Going through the motions

Austin Kleon describes himself as a “formerly ambitious person who is not feeling very ambitious at the moment.” Still, the artist and bestselling author suspects the ambition will come back in some form. And though he has called this state of “waiting to be activated” dormant, he’s also still producing meaningful work.

For Kleon, like so many others, not working isn’t an option; he has bills to pay. He has found he’s able to remain productive because he just keeps showing up. Every day Kleon heads to his workspace—a studio he built in his backyard—locks the door, and sits down. Pretty soon, something clicks; the work gets done.

Assigning artificial deadlines and signing up for obligations like speaking gigs he doesn’t necessarily want to do at the moment helps. Two of his books, Steal Like an Artist and Keep Going, stem from talks he gave at conferences. There’s nothing like the pressure of a keynote presentation to really get the creative juices flowing, he says.  

It’s not about hustling, per se; but those external deadlines light a fire and force him to focus. He tricks himself into being ambitious.

That discipline has helped him produce four books, a blog he’s written for 17 years, and a newsletter that he’s sent consistently for nearly a decade. At the same time, Kleon emphasizes the importance of patience and “waiting for some sort of that desire to come back.”

“Ambition comes in waves. When you’re younger in particular, you want to make your place in the world, and you have the drive to get there,” Kleon says. “When you get there, you have to stop and look around and figure out where you are and where you want to go next.”

This is a rejection of an ideal that society glamorizes: Less “move fast and break things” and more slow down and go through the motions, Kleon says. Both have their place in our lives at different points; often the hardest thing you’ll do is accept that the latter is just as important as the former.

“That phrase, ‘going through the motions,’ in our culture it’s a pejorative,” Kleon says. But it is often half the battle. Even when they don’t feel particularly inspired, musicians strum the guitar, dancers go through their positions, athletes run laps. Sooner or later, that discipline will spark something; ambition is reignited.

“Going through the motions is the very thing that kick-starts the engine of the work,” he says. “If you’re not ambitious, you just have to go through the motions until you feel some sort of genuine energy come forward.”

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