Is this deadline stressing you out? Unpacking the pressure around turning 30.

This post was originally published on December 20th, 2021 as I had just turned 29 and was looking at my next birthday being the big 3-0. Now, at the beautiful age of 30, turning 31 later this year, it felt time for an update with a little more wisdom.

There's a lot of societal pressure around 30. If you let them, the opinions can really start to distort your view of yourself, your progress and how you should feel about your life. The crazy part is, those opinions can be coming from people ranging from your mother (for most people, an important perspective) to that girl in your high school class who always seemed to have it together and you know you're going to see at the reunion for 20 minutes next spring (objectively, way less important), it's very common for women in their late 20s and early 30s to subject ourselves to an enormous amount of comparison game around this date.

Regardless of whether your 30th birthday is coming up or already past, when I bring up this date, I'd bet most of you immediately bring to mind a checklist of the things you want or wanted to have by 30:

  • Ideally a husband (or wife), but at least a serious boyfriend (or girlfriend).

  • A job that you like, that is paying you well and where you've gotten at least one promotion (for me, it was to the "Director" title).

  • A grown-up home (back in my mid-twenties, I dreamed of a 1 bedroom apartment in NYC but for others, it's a full-on house!) that's comfortable and decorated in my style.

  • So on and so forth.

There's nothing really wrong with having these lists. Or a "by 40" list. Or "by 60." What interests me is how accurate these lists are and what having these lists do to us.

So in this article first, I want to break down:

  • Why we feel timeline pressure (why is turning 30 so scary to us?)

  • What timeline pressure does to us (when does it help and when does it hurt?)

Then, from the perspective of having already turned 30, I want to dive into:

  • why turning 30 is great

  • how to manage the timeline pressure around any age so that it makes your life better not worse.

Why turning 30 is a big deal and how to get over timeline pressure and comparison game

The answer to why turning 30 is a big deal is a cultural one, not an objective one. Said differently, it’s objectively not that big a deal other than it’s a round number and another birthday. The pressure around this age is one that we’ve developed as a society and thankfully, in the past decade or so, has become increasingly irrelevant as more people have started talking about the oversimplification around this date. But that’s not to say that the cultural narrative around 30 is gone. So let’s dive in.

Why we feel timeline pressure (why is turning 30 so scary to us?)

As humans, we’re biologically wired to compare ourselves against things. Why? Because part of our biological wiring is to figure out how to do what we need to do with the minimum effort. Think about it - why would you waste your energy climbing a tree to pick apples when using a stick to knock them off takes way less energy, energy you might need if a tiger comes around the corner and you need to run for your life!

Comparing ourselves to others is like a mental shortcut to decide if we can feel good or not based on “are we better than them?” without having to deal with the much harder evaluation of “are we good?” This is a common part of sales psychology - often you will be asked “do you want the red one or the blue one?” rather than “do you want the red one?” because it’s far easier for your brain to pick between two options (comparison) than coming to an objective conclusion that requires introspection and self knowledge.

This theme applies to far broader topics than turning 30 but pace is a key metric that we use to compare ourselves with others. Even this makes sense from a biological standpoint - if one of the fundamental requirements of humanity is to survive long enough to procreate and to procreate with optimal partners to ensure the maximum chance of your offspring survival, then of course, comparisons that related to these themes of procreation, fertility, partnering and security would feel very, very real to us.

Of course, we live in a very different time than the cavemen - we’re not running from tigers on the regular anymore. But I bring us all the way back to those days because the emotional part of our brain, the one sitting at the nape of your neck is still running the same operating system as those cavemen. We can be smart enough to have figured out how to freeze eggs, to use AI to help us do our jobs, and understood the impact that certain medications have on our mood, hormone levels, etc. but none of that overrides the very primal, emotional part of our bodies that determines fight, flight or freeze.

And in this time, the cultural narrative has doubled down on this pressure. We took the biological narrative and made it a social one - “what does it mean about a woman to be 30 and single?” they ask. Cultural references are literally endless for the “down and out single 30 year old woman” and I won’t deign them with the respect of repeating them. But this only goes to further show that society doesn’t make it easy on you not to care about your 30th birthday.

But we’re not giving up. Just because society makes it impossibly easy to succumb to feelings of timeline pressure, doesn’t mean it’s a done deal or fait accompli. But we do need to acknowledge that the fact that you might feel pressure around turning 30 is not because of some personal failing of yours or because you’re not strong enough to think your way out of it. You are battling against patterns that have been formed literally tens of thousands of years ago.

Good news is that you’re not the only one who’s set out to overcome this, which means there’s a ton of accumulated insight you can use.

What does timeline pressure do to us? (When does it help and when does it hurt?)

Whether the timeline pressure around 30 sounds more like “I’m behind where my peers are at this age” or “what does it mean about me that I’m 30 and still single” or any other version, let’s talk about what this narrative of the timeline does to us - how we think, how we feel and how we act.

When we feel the weight of a deadline at work, most people triage. We text our friends to cancel the after work drinks because "we really need to crank on this memo." We eliminate distractions and pop in the "Piano in the Background" Spotify playlist so we can zero in on the task at hand. We also tend to start to experience anxiety and stress around the outcome and what will happen if we don't get it done -  our heart rate is almost always elevated, adrenaline starts to flow, stress dreams sometimes ensue, etc.

Do these tactics often lead to us getting the task done? Most of the time. But what happens when we start applying the same feelings of a deadline to our life? To looking for a husband? To finding the "right" job? To deciding whether to move cities? To designing our lives in general?

The difference between completing a work task and these larger life decisions and objections is that generally work tasks have an objectively correct way to be completed. The goal posts are clear - analyze this data, put the chart inside the deck, write a summary page, proof read, send to boss, etc. So the timeline pressure to complete it can help us put blinders on and stop doing any of the tasks other than the necessary ones and zone in on the things that must be done.

In real life, on the other hand, there is not an objectively right way to find your partner (nor is there an objectively right partner for you - I talk more about both of these things inside Exclusive). There’s not an objectively right job for you or way to decide that it’s the right one. Same for cities, lifestyle.

Not only does everybody’s ideal destination look different for everybody, so does the path. And because of this, any efforts to compare with others or use others as a barometer for if we’re on the right track is taking us further from the “track” itself.

Because the most important thing is to figure out how to tell if somethings right for you and then applying that to these areas of your life.

The majority of women that I work with in my Private Coaching are high achieving women, usually some version of the eldest sibling, responsible kid, type-A, straight-A student. These women, far and away, have absolutely killed it at achieving against a clear path - get the grades, get into the good school, get the job, work hard, get the promotion. They know how they need to act around their family to get attention and validation. They are excellent at execution.

But along the way, in order to get so good at all of this, they tune out what feels good to them in favor of what will impress and please other people. So when it comes around to these moments of “how do I tell if it’s right for me?” they’re so far away from knowing how to answer that question that they almost ignore the question. They usually redirect it to some sort of evaluation of their life against their friends, coworkers or family expectations.

Timeline pressure around turning 30 asks us to compare your life against other people’s lives but it completely ignores the fact that we’re all supposed to have different paths and the only way to tell if you’re ahead or behind on your specific path is to have gotten reasonably clear on what you’d like your path to be.

So when does timeline pressure help us?

When we are working on something with objectively clear goals and next steps, for which the biggest barrier is focus. In these scenarios, being aware of “how much time you have left” or how you are pacing against other people who have had to complete the exact same sets of steps can be useful for motivation and strategy.

Some examples:

  • Knowing how long previous employees in your role spent in the brainstorm phase before they made a decision on the idea to execute on and started actually creating the content

  • Knowing that the majority of NY marathon runners don’t bust out of the starting line because they’re conserving energy but around mile 16 (this is a fully theoretical example as the closest I’ve come to running a marathon is screaming my guts out at my friends who have run multiple) they push themselves to pick up the pace

  • Knowing that if you make $80k a year, currently have $40k saved for retirement at 29 years old and put away 10% of your income, that you need to slightly increase your contributions if you want to maintain the same standard of living in retirement (but side note: with the power of compound interest, the difference between where you’d end up today, contributing $667 a month, ending up with $2.17M and where you want to be to keep your same standard of living, which is 2.53M is only the difference of contributing $807 a month. That extra $140 more per month ($60,480 over your lifetime) turns into an extra $360,000. That’s basically 5x free money!)

On the other hand, timeline pressure absolutely doesn’t help us when it’s on topics where we all have different paths.

Imagine comparing the speed of someone running a 400m sprint against a marathon runners first 400m. Just because that marathon runner would absolutely do it slower (because they’re on the first 400m of a much longer race), doesn’t mean that they’re failing. Imagine comparing the size of a ballerina’s apartment in NYC (where she’s making her professional debut this year) to the size of the home of someone living in Kansas City, Missouri (who loves interior design and wants to flip houses for a living). Just because the ballerina has less square footage doesn’t mean she’s off track because these two people have dramatically different needs and goals.

How to manage the timeline pressure around any age so that it makes your life better

So here we are - you know why timeline pressure comes up and that society is unfairly obsessed with turning 30 (but honestly, the narrative around women turning most ages ain’t great). And you know that on matters like finding your partner, your career progression and feeling happy with yourself and your life, it’s not helping you. But what do you do about it?

Years ago, I read a great book called The Defining Decade, all about a better way to think about your 20s, especially in the lead up to the big 3-0 (which felt very far off at the time, but how time flies!). A couple of the points the author, Meg Jay, made felt particularly relevant:

1 — Remember you are not behind if you are not living your best life by 30.

She reassures all of us that, while we feel enormous pressure from society around 30, most people "reach their potential" in terms of financial success, career success and happiness, in their 30s, 40s or even 50s. But because I’m sure your skepticism meter just went way up, let me provide you with some examples.

  • Vera Wang didn’t design her first wedding dress until age 40

  • Viola Davis landed her first big role at the age of 43

  • Jessica Chastain broke through in acting at 34 and married at 40

  • Meghan Markle met Prince Harry at age 35

  • Vice President Kamala Harris became was elected District Attorney at 40 and got married at 50

And obviously there are SO many other examples of people that are not celebrities or politicians. (And a practical note - there's not a "best" time to get married in terms of age - the data Jay cites in the book generally indicates after twenty-five, one’s age at marriage does not predict divorce.) But I also know that just because others do hit their stride later, doesn’t mean you want to be one of them.

But here’s the thing my friend, this is a matter of focus - the facts of your life right now are what they are. If you are single, you’re single. That is not something you can magically change today. So for today, you have a choice on how you think about the current state of your life - if you focus on being “ahead” or “behind,” you’re taking the facts of your life and making them mean something bad about you. But you could just as simply, look at your life today for all the things that 14 year old you would be proud of. All the things you have accomplished that you’re proud of.

You are not behind, because there’s no such thing.

2 — Use big birthdays as opportunities for clarity.

Nothing that anybody can do can stop you from turning 30 - time just works like that. But as above, we always have a choice.

There are two types of people: those who start the calendar week on a Sunday and those that start it on a Monday (Sunday, all the way y’all). Both types of people experience Sunday 11:59pm turn into Monday at 12:00am but they choose the meaning of that switch of days differently. For one it’s the start of the week, for the other, it’s not. It’s just a choice. The time is passing regardless but the story comes from how you frame it in your mine.

When you’re doing a set of 20 sit ups, is 10 halfway done or half to go? Same number of pushups - the feeling you have about it depends on the framing of focusing on your progress or the binary of completion.

So coming around to your 30th birthday (or 35th or 40th or 50th) is an objectively benign one day turning into another - but you have the power to make it mean something helpful for you if you choose the right framing.

Some more helpful framings you can use besides “am I behind because I haven’t done X by my 30th birthday” to make this day an opportunity more more clarity:

  • What have I built momentum toward that I’m excited to continue creating or building?

  • What patterns do I have in my life that this would be a good “lightning bolt” moment to shift? How am I going to help myself do that (what tools and resources do I need to succeed in making a change here)?

  • If I view this birthday as a start to a new chapter (or season of a TV show), what is going to be different about me in this season? What do I need to change about how I think or act in order to bring this new version of my character to life?

  • What are the accomplishments from the past year, 5 years or 10 years that I’m most proud of? What made them feel so good and what are some things I can look forward to or work towards in the coming years that might give me a similar feeling?

We can use birthdays as opportunities to clarity our vision for our unique lives. This approach doesn’t put us into comparison but rather the focus returning to ourselves.

3 — Don’t let big birthdays encourage the "slide."

In Defining Decade, Jay describes a trend of "sliding in" to major commitments like career and marriage - where a couple goes from dating to sleeping over to moving in together to engagement often because "it just made sense." A career version of this might be sticking with the path you’re on just because making a pivot at 29 or 36 seems too scary (but let me tell you as someone who left their corporate job to start a business at 29 - it’s possible and never too late!)

But before we move on from the topic, one of the most insightful chapters of Defining Decade was on this topic so I want to dive in for just a moment. There's a common misconception that living together before marriage (or engagement) makes a couple more likely to succeed in marriage. The data found this was not true. Couples who live together before engagement tend to be less satisfied with marriage, and more likely to divorce but this trend did not hold true for those who lived together after engagement but before marriage. She points out that couples that "slid" into living together (which probably made up a decent chunk of those cohabitating before engagement) may be less likely to break up when they should have because of the logistical difficulties and this led to more unhappy marriages than those that had actively decided based on being ready for the larger commitment.

This does not mean if you're currently living with a partner before engagement that the relationship is doomed. Jay points out the importance of the active, explicit discussion that often occurs around a potential engagement (including aligning on the vision for the future and addressing any underlying issues head on).

The key here is to make active decisions about what you want, don't just stick with what's in front of you because you're worried you won't find something better.

Don’t let a date on the calendar encourage you to accept “good enough” or what’s in front of you because of some fake deadline.

4 — Prioritize learning about yourself over exploration or achievement.

There can be a story around 20s being the time to explore and get the crazy travel, hookup, or irresponsibility out of your system. I think this leads to some of the unhealthy pressure around 30 because it becomes the time where you need to “get serious.”

But Jay makes an important point in the book, regarding this “get it out of your system" narrative. She argues that hookup culture, ever present in the romantic discussions of twenty somethings, isn't the best path to happy future.

I loved seeing this debunk. She cites a study that tracked men and women from their early twenties to their later twenties found that of those who remained single—who dated or hooked up but avoided commitments—80 percent were dissatisfied with their dating lives and only 10 percent didn’t wish they had a partner. Her main observation here was not that we should all only be dating to find our future partners but we should be dating (and not just hooking up) with the hope to learn something - learn relationship skills, get clearer on what we want in a partner, etc. Whether you are currently in a relationship or single, I love the reminder that there is value in your romantic life (whether you end up with the person or not) as long as you are learning about yourself.

When you are no longer playing the “am I ahead or behind?” game or comparing your progress against your friends, your burden of self-evaluation is in many ways more complicated. You don’t get the simple comparisons so what do we get instead? You have to evaluate how you think, feel and act against how you want to think feel and act.

When you’ve spent a long time following other people’s rules, this can be a big wakeup call because you may realize: “I don’t really know what I want.” (I know from personal experience because I had this moment plus about 30% of my clients have this sort of aha at some moment in our work together where they realize they need to rediscover what actually makes them happy.)

If you feel like your tendency is to people please and try to achieve on some external rubric, let 30 be your opportunity to start rediscovering yourself. Look at every dating scenario not about whether it worked or not, or “it was just to have fun” but rather, what did you learn about yourself? What did you learn about what you do or don’t want in a partner?

This shift in how you evaluate each situation makes them actionable and helps orient your thinking toward your own self-knowledge, which is the best 30th birthday present you can give yourself.

Remember you are not alone. There are hundreds of thousands of people who feel similarly and while often this feeling can feel excruciatingly lonely (especially if most of your close friends are in relationship or having the type of career success you're seeking), it can help to remember that many others feel this and more importantly, many have gone on from this place to live happy and fulfilled lives.

And if you are feeling lonely, I am here to tell you that I see you and you have a place in my world as you navigate this transition.

You are doing just fine. As a now solidly thirty year old, I can happily report that feeling defeated or like there's something wrong with you is not required. Your life can be amazing and you have time.


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