You can reach every goal you’ve ever set for yourself and still feel like your life lacks value. That isn’t ingratitude, and it doesn’t mean something is wrong with you.
I know, because that’s exactly where I landed.
By the middle of 2022, I had won. The title I wanted. The job I wanted. The zip code I wanted. The downtown condo I’d always dreamed of. The car. The relationship. Check, check, check, check, check, and check. I had arrived everywhere I’d been working so hard to get.
And when I finally got there and looked around, I waited for the feeling. You know the one. Accomplished. Proud. Like you’ve finally made it. It never came. That was my aha moment: I had everything I’d ever wanted, and I didn’t feel the way you’re supposed to feel when you get it. I felt deeply unfulfilled. Nobody tells you that arriving can feel exactly like being lost.
Maybe I hadn’t been making the right choices at all. I’d spent years chasing a title, a label, a brand, a paycheck, and a set of expectations I’d been led to believe would make me happy. And here’s the part that stung: nobody forced those expectations on me. I expected it of me, too. Now I was standing in the middle of everything I’d wanted, and it didn’t feel good. Today I’d call it being out of alignment. At the time, I was just confused.
Then, after that aha moment, life started clearing the shelves for me. My relationship ended. The company I worked for closed its doors. Suddenly I had nowhere to be and no one to serve. For a woman whose whole identity ran on being needed, that isn’t a pause. That’s a free fall.
It’s a strange thing to stand in a place where you’ve lost what you thought was your value. You can see it as an ending. Or you can decide it’s time to reset your entire life and look at it as a beginning: take a good, honest look at who you are, what you’ve been chasing, and where you’re headed, and realize it’s all a choice. Then you start choosing differently.
2023 became the year I started making different choices. Here’s what it actually took.
Screaming in the car wash
First, I fell apart a little. Okay, a lot. I slept a lot. I cried a lot. I shouted into my pillow a lot. I also discovered that a drive-through car wash is the perfect place to scream. It’s private, it’s loud, and your car comes out shiny. (Pro tip. You’re welcome.)
Every morning I woke up unsettled. No Zoom meeting to sign into. No panicked texts. No Slack pings. No important meeting to anticipate, or dread. Just me and a very quiet phone. I had become deeply addicted to being needed at work, and without it, I had to face something hard. I had given myself away to my career, piece by piece, and I had never really learned to find what I needed from within myself.
My programming kept saying get to work, get to work, get to work. That’s what I’d been conditioned to value. When I was working, I was valuable. When I wasn’t, I wasn’t. So when the work was gone, I didn’t know what I was worth. I didn’t know what to do with myself, or what I even liked to do with my time. I didn’t even know what to complain about without the irritants of my career. Do you know how disorienting it is to miss being annoyed?
Lost and hopeful, all at once
In the middle of February 2023, I arrived at a health retreat in Costa Rica feeling two things at once. Lost, like my life lacked value. And hopeful, like I was standing at the edge of something big. That is a very confusing combination to pack for.
While I was there, I learned that I could only show up in the world, and shine, as brightly as I could love myself. For a woman who had poured everything into her career and her relationships and saved very little for herself, that was a whole lot of homework. I looked at the key areas of my life I wanted to change. I talked about how each one had always been, and then I set a vision for how it was going to be going forward.
For the first time, I could see who I wanted to be without defining myself by what I had been, and how I wanted to show up in this world. When I looked back at everything that had happened, professionally, personally, and romantically, I braced for the anger, the resentment, the regret. It wasn’t there. What I found was acceptance, for all of it. Every single thing up to that point, the good, the bad, and the ugly cry, had landed me right there, in that moment.
All that mattered was how I chose to show up now, and every day after that. In every way, that was a choice, and it is all we can really control.
To-do lists a mile long
By then I knew a few things. I knew I was done trying to be seen in rooms where everyone was trying to be seen and no one was actually seeing one another. You know those rooms. For years, that meant being the loudest, most boisterous person in there, or always trying to say exactly the right thing. Exhausting. I knew which parts of my career I loved and which parts I didn’t. And I knew where I wanted to be: working alongside women finding their power through purpose-driven work, and helping them any way I could.
Within a few months, ready to jump into action, I started Beespoke Brands, a small consulting business. I worked with friends who were in business for themselves, helping them get organized around what needed to happen next and where they were being slowed down. That work felt deeply purposeful.
It also showed me a real problem. These women were so busy doing the work inside their businesses that they couldn’t figure out how to grow, expand, or juggle everything the business required. They were exhausted and overwhelmed, mostly because they carried the lion’s share of caretaking in their personal lives, for parents, children, and the people they love. They didn’t have the tools, or even the time to ask for help. They were drowning in to-do lists a mile long that knocked the wind out of them every time they looked. I wanted to help them, and most of them couldn’t even find the time to work with me.
I knew there had to be a better way. And I knew there was a physical limit to how many women I could help one at a time. So I set out to bring these women the support they needed, in a way that could reach as many of them as possible, through tools that could show each of them her next best step, based on the time and energy she actually had that day. Most of all, I wanted to create a place that felt like home: supportive, free of judgment and deadlines, and able to help her keep momentum even in the hardest of seasons. That’s where Wayfindher® came from.
I packed my career
Looking back on more than two decades in corporate, I can see how the pieces set me up for this, even the jobs and roles that didn’t make sense at the time. Knowing what to do next. Knowing how to think about a business. Knowing how to approach a brand, how to move through product development, and which steps to take in what order. All of it came with me. Turns out, I didn’t walk away from my career. I packed it.
That became a second realization behind this work. The experience a woman has built up to now comes with her, too, and she can use it to build something of her own.
That doesn’t mean I always follow my own advice. I break the rules sometimes, more often than I’d like to admit, and I ignore things I would have told the people who worked for me. But the foundation is there. Whatever experience you’re carrying, your foundation is there too.
Founder, intern, and IT department
The first thing that had to go was my ego. When you take on work like this, you have to be willing to do every job, including the grunt work: the heavy lifting, the blood, sweat, and tears that go on behind it. No job is too small. It’s one thing to put “founder” in your bio. It’s another thing to be the founder, the intern, and the IT department, all before lunch.
The second was my idea of outcomes. I can’t control most of what happens to this business. What I can do is keep listening to women and keep trying to build the right product, so it becomes the best it can be for them. Whatever shape Wayfindher ends up taking, including ones I can’t imagine yet, doing the work, bringing it to life, and letting it unfold the way it needs to has become my most important goal. I refuse to set myself up for failure by setting goals around things I can’t control, or by shrinking the dream I have for this business.
It’s quiet out here
Some of it is the work itself. Infrastructure, technology, and detailed documentation don’t play to my strengths, and I’d much rather lean into the pretty stuff people actually see. Every day I look at my list and watch myself drift toward the pretty stuff like a moth to a very well-designed flame. I know what I gravitate toward, and I know what I gravitate away from. That’s the daily battle.
But the even harder part is building in a vacuum. It’s quiet out here. Really quiet. There’s very little feedback and very little validation, so the voice in your head becomes the most important relationship you have to manage. Every day I tell myself that what I’m doing is meaningful and that I’m fulfilling a purpose. What everyone else says doesn’t matter, and the reality is, most days they don’t say anything at all, because honestly, no one cares about it like you do.
The relationship you have with yourself, the confidence you need, the conversation you have to get past imposter syndrome and the question of whether you’re capable of this: that’s the real work underneath the work. The tools out there today make all of us capable of things we couldn’t have imagined. After 20 years in product, I can now sit down and build a product without an engineering team, and that still blows my mind. But as amazing as that is, the daily wrestling match with self-doubt and uncertainty is by far the hardest part of this for me. Self-doubt doesn’t care how many years you’ve put in or how many problems you’ve solved.
Face Everything And Rise
I’m not here to tell you to leave a perfectly good career to start a business of your own. That call is yours. But if you keep asking yourself, “Why am I not doing this on my own?”, that question deserves an answer. Try.
Fear lives in your head, and most of what it tells you isn’t real. I remember it this way: Face Everything And Rise. That acronym gets me through every single day. Some days it gets me through every single hour.
If you can get out of your own way, I want you to know a few things. There are so many tools out there now that will help you do it. There’s a community out here that will help you do it. And you’re not alone.
We’re all scared. I’m terrified. We all struggle with courage, with putting ourselves out there, with the same set of fears. If you’re afraid you’re not enough or not capable of this, you’re wrong. We’re all capable, and every one of us needs clarity, confidence, and community to get there.
I also want to be honest about my situation. I’m single, and I don’t have kids or financial dependents (unless you count two very spoiled Boston Terriers), so it was less complicated for me to take a big risk. I’m not suggesting you dive headfirst into years without a paycheck to chase your dream. Decide which risks are worth taking for you, and build yourself a safety plan. If you do, you’ll know when the time is right. That might mean working on your business at night or on weekends while you keep your job, so you’re ready when you go. As for me, I gave myself a runway to make it or break it, and I take it one very frugal day at a time.
For the woman I was in 2022
I’m building Wayfindher for the woman I was in 2022, and for every woman who has looked at the life she worked so hard for and wondered, quietly, is this it?
No woman should have to build something of her own alone. She shouldn’t have to wait for the perfect week, a clear calendar, or anyone’s permission. Whether she has a full day or one hour at the end of a very long one, she deserves to know her next best step, and to take it without judgment.
That’s the whole mission. Everything else is how I’m trying to get there.
If you’ve already made the leap, or you’re sitting at your desk tonight wondering whether you could, hit reply or leave a comment and tell me what you’re weighing. I want to hear it.
~amy
Wayfindher is built with women, not just for them. Join the Waitlist and tell us where you are: wayfindher.com/get-involved/founding-cohort