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Personally and professionally, the weight of trying to figure out when it’s the right time for something is a heavy burden, Leah argues. 

First off, the answer is no. There could be worse times or better times, but the idea of a right time to do anything is, or ought to be, patently ridiculous (or as Perelel Founder Alex Taylor told me for issue no. 3, “There’s never a perfect time to start a business, but maybe there’s a less complicated time” when talking about her decision to dive into building her company). I’ve been caught up in wondering about the right time for something more than I’d care to admit: moving, trying to have a child, looking for new jobs, buying something for our house. Matters small and large have captured mindshare in my brain and led me to hem and haw, stress and fret. 

How mentally cruel, too, is the game of convincing yourself that it is indeed the right time only to see the option evaporate in front of your eyes? I’ve had that particular breed of painful whiplash hit me when searching for new jobs and new homes, both relatively monumental decisions that require you to think and imagine before deciding, yes, okay, this is something worth uprooting my current stability for. The time is right! Yet you can reach a moment of certainty and find that the option is no longer viable (the job goes to a different candidate; the home to another buyer). Some of the same twisted-knife feeling exists when it comes to family planning, too. We focus on not getting pregnant for years, only to talk and think and debate, decide it’s time…and then perhaps realize the universe has other plans. 

I’m grateful the women I canvassed for opinions and insights for this piece didn’t look at me blankly or meet my queries with dead silence. It’s more or less half a dozen big questions crammed into one: Is there a right time? How do you know? Is feeling paralyzed by worry and doubt completely normal and to be expected, or a sign of something that’s not quite right? Those questions are hard enough on their own, and if you layer in any external factors (like the housing market or fertility), it can feel pointless. When you reach the point of peak frustration, it’s tempting to throw up your hands and embrace stasis. An immobile stone might gather all types of moss, but at least it won’t find its path rerouted. 

“I’ve learned to lean into the idea that everyone has their own path. Compare, despair. If you stress too much about something before it happens, you’re basically putting yourself through it twice,” advised Amanda Jones Vaughan, a super-talented, and super kind, business development and marketing star. “It’s about taking those deep breaths and enjoying the magic and blessings you have. That’s another thing that comes in with timing: Really understanding what your personal situation is because everyone’s path is different. Career or family planning or relationships—you have to be inspired and motivated by and learn from others, but you won’t be able to move in someone else’s path because it’s not your path. Your timing could look completely different than someone else’s.” 

She hit right at something I hadn’t stopped to consider before: whether much of the worry about the right time is tied up in comparative thinking. Unwittingly, I’d been casting my journey against what I’d seen friends and others on Instagram do, subconsciously creating benchmarks or this-is-what’s-normal paths. We’re all far too familiar with the negative self-talk that can come with contrasting what we have to another, but attempting to use those comparisons as a helpful tool or guide can be just as insidious.

“Certain generations stayed in jobs for decades and decades, and I think there’s a culture these days where we’re jump-happy and go from job to job. There’s no right or wrong way to do it, but that’s a gut check I have for myself. Do I feel like I should leave this job because all my friends were in jobs for two years and then changed, or is this really the time for me to be doing this?” Amanda’s most recent move took her from three years spent handling partnerships and VIPs at Net-a-Porter to Over The Moon, the gorgeous destination for all things bridal. Her new role is bigger in scope, better in pay, and allows her more autonomy, but, even still, she didn’t immediately know it was the “right” time to make the move and put thought into the decision. 

“I wasn’t looking at all. [The role] took shape and turned out to be something I didn’t even know I was looking for,” she shared. “I knew there would be longer hours and a leaner team, and I was heading into a time where growing our family would likely become top of mind. Sometimes you just have to jump.” Over The Moon had always been on her radar—she was acquainted with founder and Vogue.com Weddings Editor Alexandra Macon and had discussed a different job a few years earlier before realizing it wouldn’t be the right fit—and found herself professionally affected by changes wrought by the pandemic. “It made people look at their jobs differently. I loved my role, but a lot of the things I was doing had been put on pause because of the pandemic. I was eager to get back to what my role was, but there was an element of, ‘Life is so short to be waiting on something’—the job could look completely different when we’re ‘out of this.’ There was so much that was good about it, but so much that was comfort, too. The decision [to leave] was about giving myself that gut check: Why am I here? What is my boss’s job? Is that a trajectory I want to be on? Do I want to be at the company in a few years? What am I getting out of it?”

Her list of questions felt like gold as it poured over the phone line. Those questions are so important to ask yourself when weighing a new option, job hunting, or perhaps just on a regular basis. A full slate of affirmatives can still leave doubts as to whether it’s the “right time,” but at least it lays out a pretty convincing argument in black and white. When I’ve asked my own questions about career paths to Marcella Kelson, the maternal wellness life coach we’ve been lucky enough to feature in previous issues, she’s always advised thoughtfully examining your current situation. Is there room to grow and expand upon what you need or want? What more can you learn? To me, it felt like her safeguard against making a decision at not the right time. Amanda offered up a similar sentiment: “I struggle with imposter syndrome and feeling like, ‘Have I given it my all? Should I stay where I am because I owe it to myself and the company to contribute and soak up as much as possible rather than hopping ship? Am I taking the easy way out?’ At the end of the day the answer is usually no. You’ve done a wonderful job, and your heart’s not in it. That’s maybe why you’re not performing or feeling a certain way.” 

As a final check, she takes stock of internal opportunities before making the call on timing. “Is it your dream role but not your dream company? Or your dream company but not your dream role? Is it time to make a change if neither of those are true? Are you ever going to get the perfect opportunity? In my opinion that’s rare—but you can also make your own perfect.” For her, that means stepping back for a fuller picture, noticing all the good, and never forgetting that there are unglamorous or not-so-fun parts of any job. “Creating your perfect is about being grateful and appreciative of where you are; that element of looking back, picturing what you wanted a few years ago, and realizing you’re there or even past there. It’s looking around you and listing the things you’re doing that you’re excited about or the people you get to work with or learn from.”

While much of our conversation focused on career and deciphering when, and how, to move different building blocks and stepping stones into place, we also touched on the personal questions and conundrums that often leave us bewildered as to whether it’s the right time for something. I am personally a big believer in the universe course-correcting you as needed (or providing “God winks” if that’s a phrase you’ve heard before). You might think it’s the right time for something, but if it’s not meant to be, it simply…won’t be. There’s humility to be had, painful lessons to be learned, and setbacks that can feel soul-crushing in their weight. Anyone who’s struggled to have a child or had an enforced nomadic existence, two things that have hit me with a piercing intensity, will understand the futility of worrying too much about whether something is the right time. In hindsight, it’s easy to see why or how it wasn’t, but when you’re living it, things can feel drastically different.

“Recognizing when things or decisions are emotionally charged, I’ve found it’s best to try and chop things off little by little,” Amanda shared, pointing to the gradual, bit-by-bit conversations she and her husband have started to have about when and if they’d ever move out of Manhattan. “I remind myself everyone is on their own path, especially when it comes to building your career and your future family. It’s always going to look different than how you envisioned it and how your friends or people around you are experiencing it. It’s reminding yourself that Instagram is just a snapshot of reality, and everyone is going through something.”  

Our talk left me inspired and with a renewed sense of calm contentment. This question about a “right time” always feels a bit ridiculous since I know one will never exist, yet I can’t seem to stop myself from asking. Perhaps my biggest lesson isn’t that I should stop worrying about timing (a fool’s errand), but connect instead with other smart, passionate people to hear their take on it and be reminded that things will unfold as they should. Whether it’s the stuff mostly beyond your control (finding the perfect home, getting pregnant) or those that you can do something about (optimizing your current work), there’s never a right time. But being reminded of that by women who are living and breathing it alongside you? It’s always the right time for that. 

[This story first appeared in issue no. 4—order the full issue here]

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