Forget Your Goals
Megan Hellerer shows us a better way forward
Welcome to Mess & Noise. Last time, I sent a pupu platter of links while I was deep into Pushing Back with Tact — my minibook about disagreeing at work like a class act — dropping later this week. With a paid subscription you’ll receive all my books, some swag, and unlimited access to my future hydrogen-powered jet (no flights included).
I used to regard life coaches with indifference and a little suspicion. In an unregulated field, anyone—even the hottest mess you know—can charge more by the hour than a licensed psychiatrist to give life advice over Zoom. But the coaching industry has become massive, generating over $4.5 billion as of February, 2024 with about 70% of U.S. coaches being women.
This gives personal coaching the Pumpkin Spice Latte effect—popular with women, so easily dismissed as lame, frivolous, or a Girlbossy scam.
If I had a Statista membership (have I mentioned paid subscriptions yet?), I could probably show you an inverse correlation between the rise of personal coaching and the decline of religion in the U.S. It suggests a simple theory: coaches are filling a void left by modern secularism. We have a deep, culturally ingrained need for guidance, and without pastors, extended family, or strong communities setting norms and milestones for us, we turn to coaches to answer the eternal question: “What should I do with my life?”
Megan Hellerer completely changed my view of coaching. Yes, her clients (including me, about 10 years ago) come to her asking what they’re doing with their lives. But Megan doesn’t offer vague advice like “follow your intuition” or “listen to your gut.” She actually shows you how to do that — the intuition and gut feelings are the outcome of working with her.
Megan’s brilliance lies in the exercises, thought experiments, and beta testing she guides you through, helping you locate what she calls your “Inner Navigation System” (INS)—so you can access it for every decision in your life, from career moves to what’s for dinner.
Megan’s coaching story begins with her crying on the bathroom floor between meetings at Google, where she worked in Strategic Partnerships. Up to that moment, she had done everything right: she was a star student at her Manhattan private schools, played sports, mentored others, got into Stanford, and landed a coveted job. And she was miserable.
I love her story, especially now, when we’re all addicted to our phones and algorithms aren’t just “guiding” us—they’re making decisions for us and shaping our thoughts. In a way, we’re all working for Google and other big platforms, and I often feel like I’m crying on their bathroom floor.
Fortunately, Megan turned her breakdown into a period of experimentation, rebuilding her life as a different kind of strategic partner—one who helps people understand their unfulfillment and clarify steps to living life their own way. Her new book, Directional Living, promises that you can “achieve more, with less anxiety.”
Here are a few key points from Megan’s book to set up our conversation below:
Megan advocates for “Directional” over “Destinational” living. Instead of setting rigid goals like “Make partner in 5 years” and enduring pain along the way (only to ask, “Is this it?” when you get there), she suggests a gentler approach: follow your curiosity and take small steps without the pressure of predefined outcomes.
She offers frameworks (she’s an ex-tech exec, of course there are frameworks) that help de-risk big decisions and give you the space to reflect on them.
Her method has worked for hundreds of clients, though she keeps their identities confidential—except one: a bartender from the Bronx named Alex, who worked with Megan and later ran for office. That bartender is now Alexandria Ocasio-Cortez, Democratic representative for New York’s 14th District.
Now, let’s hear from Megan.
This book comes at a pivotal time: Millennials are hitting the midpoint of their careers, many feeling burned out or disillusioned by the success myth they’ve been sold. Meanwhile, job cuts are spiking, especially in tech.
You talk about the “gift of desperation” and how hitting rock bottom in your life or career can be a turning point. What would you say to someone who’s been laid off or is thinking of quitting without a backup plan? Any first steps or mindset shifts you'd suggest for someone who’s spiraling out? (Asking for a friend.)
This is exactly why I wrote my book—it's the best way I've found to move from misery to meaning and get on a path toward true fulfillment. In the book, I walk you through how to make this shift.
In the meantime, my advice would be to create an intentional exploration period (some people call it a sabbatical) if you can. This isn't a vacation or catch-up-on-life-chores time; it's for reflecting and resetting your approach to work and life. Decide on a timeframe—whether it’s a month, three months, or more—and make it as stress-free as possible. Use this time to commit to not figuring everything out right away, giving yourself the mental space to discover new possibilities.
If you can't take extended time off, try to carve out smaller windows—maybe Saturday mornings or a few weeknights. Even a little time can help.
For those spiraling, here’s my pep talk: It doesn’t have to be this way. There’s a solution, and it’s more attainable than you think. You’re not alone, and it’s not your fault. You followed the path you were taught, but that path was flawed. Now, it’s up to you to change it, because nothing will improve unless you do. If what you're doing isn’t working, why not try a new approach? As they say in 12-step programs, “We can always refund your misery”—you can go back to the old way anytime. But first, give yourself the chance to try something different. It worked for me and for many others, and I assure you there was nothing exceptional about any of us. It can work for you too.
Your take on Imposter Syndrome was such a breath of fresh air! It’s been a saturated topic for professional women over the last decade, and the advice is always to “know our worth” or power-pose our way into confidence.
You argue that we are…imposting (my new made-up word)— not faking our skills or expertise, but contorting ourselves to fit rigid norms that were established long before we arrived on the scene. And it’s exhausting. At the same time, “bringing your whole self to work” can backfire for women. Have any of your clients managed to succeed on traditional career paths — suiting up, playing the game, and enduring the politics while still being able to look themselves in the mirror?
Or is it that the traditional working world — whether it’s an old-school bank or a tech-bro startup — just isn’t designed for most women, and we should opt out to build our own things?
There are absolutely people who’ve built fulfilling traditional careers—and even switched into them because they were so fulfilling! I’ve worked with people who start at Google while we’re working together.
The key is to take a Directional (non-traditional) approach to a traditional career. It’s not about what you do, but how you do it. We’re looking for alignment, wherever that may be. If a traditional career aligns with you, great! If not, just as great. I don’t see a moral hierarchy between traditional and non-traditional careers.
Most people, though, take a traditional approach to a traditional career, which is why they end up dissatisfied. They choose it for the "stability" and the optics, but build their careers in a conventional way.
AOC is the perfect example of taking a nontraditional approach to an established career path. She does it so well because it’s so aligned with her. She didn’t start with an end goal of being a congressperson or holding political office—she didn’t even expect to win! She ran because it felt directionally right and followed her curiosity.
That said, operating in traditional worlds untraditionally—like being a woman in any corporate career—is not easy. This is why alignment is so important. If it’s aligned, it’s likely because you’re uniquely suited to disrupting and challenging the status quo. That’s probably part of your purpose and what makes the work fulfilling for you.
A key part of your Directional Living approach is tuning into your INS, or “inner navigation system,” to recognize what sparks joy and what doesn’t. What feels “light and right” versus “hard and heavy.”
This must be challenging for someone who’s never tapped into their inner knowing before, or feels they’re not wired for it. How have your clients shifted from spreadsheeting and optimizing to sitting still, listening, and resisting the urge to act on the first impulse?
I was that person, and I wrote this book for people like me. (Not trying to give a cop-out “buy the book” answer, but this is one of the main hurdles I address.) It’s frustrating when all you hear is “trust your gut” or “follow your intuition.” Like, WTF does that even mean?! That’s why I created a practical, step-by-step guide to help you tune into your INS. It’s such a simple framework that anyone can learn, no matter where you’re starting.
You begin with small, low-stakes decisions—like what to have for dinner, which exercise class to take, what to wear, or what book to read. You practice, build the muscle, and gradually move on to bigger decisions—whether to attend the baby shower, how to spend Thanksgiving, or whether to speak on a panel. Eventually, when it comes to major life decisions—where to live, whether to take a job, or invest in a relationship—the process will be the same.
Being a mom can often be “hard and heavy.” I don’t think anyone can fully prepare for how much life changes and how much work it takes to raise kids, at least in this country. Parents are constantly pulled in different directions, with little time to choose their own day-to-day direction.
Has becoming a mom changed your approach to Directional Living? Are there any new caveats or adjustments that have come up for you?
Becoming a mom has only reinforced my belief in Directional Living!
There are two parts to this: navigating parenting directionally, and navigating your career directionally as a mom.
As for parenting, I’m convinced Directional Living has made me a better parent. Having this framework helps me parent more easily and with less anxiety. I’ve even joked with my editor about writing a book called Parenting Directionally because these principles fit so well.
Like with a career, everyone has an opinion on the “right” way to parent. But there’s no one right way—just the right way for you, your child, and your family. Trying to parent by external “shoulds” will leave you anxious and overwhelmed. Instead, you need to follow your own Inner Navigation System (INS).
Parenting, like Directional Living, also requires flexibility. There’s no way to plan everything, especially with kids. You can make a million plans—what you’re going to feed them, what school they’ll go to, what activities they’ll like—but they’ll have their own ideas. It’s impossible to control everything.
If you try to parent destinationally, attaching yourself to outcomes like, “My child will walk by 9 months” or “My child will love sports,” you’ll be setting yourself up for frustration. You can expend a lot of energy trying to make those outcomes happen, but why? If you insist on following a rigid, predetermined plan, it’s going to be hellish for both you and your child. Parenting destinationally makes you feel like you’re always doing it wrong.
Directional Living allows for evolution and change, which is crucial in parenting. The question becomes: “Is this directionally right for my child or family right now?” It creates more flexibility without feeling chaotic.
It also lets your child explore and become who they are, instead of who we think they should be. You’re present and responsive to their evolving interests, which allows for curiosity and genuine connection. Directional Living is about being present, whereas Destinational Living is always future-focused.
This same approach applies to adults, too, but it’s more obvious in parenting because you can see how ineffective Destinational Living is with children.
Now, to the part of your question about the unglamorous aspects of parenting. Cleaning up mashed banana for the fifth time or doing endless loads of laundry doesn’t spark joy. But that doesn’t mean it’s not aligned. Most of the “hard and heavy” parts of parenting are about repetitive caregiving and biological needs, which can be annoying even in taking care of our own bodies. It’s less about whether these tasks are aligned and more about asking, “What is this in service of?” For me, raising my daughter is deeply aligned, even the parts I don’t enjoy.
You may not be able to opt out of these things entirely, but you can ask how to make them more tolerable. For example, if bedtime is brutal, maybe your partner handles that while you take mornings. And of course, when possible, outsourcing and asking for help is crucial.
Side note: We don’t have enough support for parents, and we should absolutely invest in revolutionizing childcare and caregiving systems.
Emotional labor is another challenge in parenting, but that’s true in any relationship. Parenting is unique, but dealing with your partner’s quirks can feel just as heavy sometimes. However, investing in growing your relationship is probably still aligned, even if parts of it aren’t fun.
One key difference with parenting is that it’s one of the few permanent things in life. I often say, “Nothing is permanent,” but you can’t just try parenting and then decide it’s not for you. (Enter: argument against forced birth.)
As for navigating a career while parenting, you have less time and less control over your days. But this doesn’t make Directional Living any less valid—it actually makes it more important. With less time to waste, you have to focus on what really matters. Even if you get fewer opportunities to explore your curiosities, you still need to make decisions using this framework.
For example, I would have done more to promote my book if my 1-year-old wasn’t teething, started daycare, and started getting sick every other day, which meant, I wasn’t sleeping. But that doesn’t mean the ideas I had for the book weren’t directionally right. Was it frustrating? Yes. Did I scream into my pillow, saying, “WHY NOW!?” Absolutely!
But holistically, both my book and my baby are aligned parts of my life.
The only issue is my impatience, which comes from a Destinational mindset. I want things to go faster, and that’s where frustration creeps in.
Your book is about choosing expansiveness and possibility over rigidity and forced outcomes. That said, are there any hard-and-fast rules in your life? 😄
Any non-negotiables or boundaries you’re strict about to create space for more possibilities? (For instance, I make one day per week “Do Not Disturb” — no meetings, no emails, no texting while I’m writing, and I love hearing about other people's rules or tricks for protecting their time.)
I do have two “rules” related to sleep. Sleep is a priority for me, and I don’t sacrifice it. These habits started when I quit Google over 10 years ago and haven’t changed. One is that I don’t set a wake-up alarm (except for rare occasions like early flights, but I try to avoid those!). The second is that I take a nap every day and block out “siesta” time, which is almost untouchable. I’m a much happier and more effective coach, writer, and human when I stick to this.
Most of the time, I rely on guiding principles rather than rigid rules, because flexibility is crucial. Lately, I’ve been operating on “baby time” and “media time,” both of which tend to be last-minute and non-negotiable. That said, I’ve found that setting intentions and guidelines for how I work best is still helpful, as long as they’re adaptable. I call this “structured flexibility.” For example, the days I have meetings may change, but I always try to batch them.
Early mornings—before interacting with anyone—are still my most creative and productive time for focused or creative work (like writing). It’s been tough having an early-riser baby, but once I was no longer needed for nursing, my partner and I started alternating mornings. I’ve asked him not to interrupt my morning time unless it’s an emergency, and he honors that time as sacredly as I do. I also try to get on a sleep schedule where I wake up naturally, even if that’s at 5 a.m. I’m very disciplined about using mornings for dedicated projects that need my full attention, and I decide ahead of time what those projects will be.
I’m also particular about my schedule. Like you, I have “people/talking” days and “no people/talking” days. I batch meetings and try to avoid having just one meeting or client session, to prevent the task-switching costs, especially between “people-ing” tasks, which require a different kind of energy for me.
One of the biggest challenges in promoting this book has been that many of these rules and principles had to go out the window. There was no way to fit all the interviews and media into my usual “people/talking” days, and I definitely felt the impact. It was a great reminder of why I created these guidelines in the first place!
A more recent commitment is to strength training (at home) three times a week. I only skip it when I’m sick. I had a lot of postpartum back pain, but I found an amazing postpartum trainer. Strength training has been a great way to reconnect with my body, and the achiever in me loves seeing the data—like the weight I’m lifting going up. Plus, I love that the “results” have nothing to do with how my body looks.
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I hope you’ll check out Directional Living. I listened to it on Audible and it was like having a kind and wise BFF calling you with magical, life changing advice.
👋 Oh, hello new subs! 👋
In 90s-teen patois I’d like to say big-ups to Stephenie C., Sally C., Chris C., (is this the entire C. family?) and Roger W.
It’s cool to see subscribers I’ve never met outnumber the subscribers I’ve hugged and smelled IRL. I’ve been writing this newsletter sporadically and un-seriously since 2021 with no idea what I’m doing, so whether we’ve smelled each other or not, it’s heartening to have you along for the ride.
I think I’m writing about smells & nostalgia next week 🕯️