Someday Arrived
On equity, shame, and the future I thought was waiting for me.
This is not about a specific company.
It is not about a specific founder or team.
It is not about a specific decision.
It is not even the full story.
I’ve spent my entire career in startups. I’ve worked at companies I was/am convinced would become massive. I’ve worked at companies that no longer exist. I’ve worked at companies that shaped who I am as a person and as a professional.
This is simply one part of my experience. But it’s not the full experience, and I want to acknowledge that.
And while I could tell the public version of the story, the version about how acquisitions are good for communities, how startups create opportunity, how everyone learns something valuable along the way: I already know that story and I’ve already shared it.
And I believe that story.
But this is about the quieter story.
The one that only exists in my body.
The one about equity.
A company I worked for many years ago was recently acquired. When the acquisition documents arrived, I was excited/confused/worried/cautiously optimistic. The former employees were frantically texting each other to see who had any information. We were informed there was a transaction happening, and then we waited 2 weeks before finding out what it meant for each of us.
I opened the email and saw the number.
And I immediately felt ashamed.
Not disappointed.
Ashamed.
The dangerous thing about equity is that, over time, it can start to feel like a numeric representation of your value.
Your contribution.
Your character.
Your work ethic.
Your value.
Of course, I know intellectually that isn’t true. I've been around startups long enough to understand how equity decisions get made. I help make those decisions today. I understand funding rounds, dilution, risk, cash constraints, hiring markets, leverage, timing, negotiations, and all the variables that influence who gets what.
I understand all of that.
But understanding something intellectually and feeling it emotionally are two very different things.
Because when I saw that number, I wasn’t thinking about capitalization tables. I was thinking about what it meant.
And for me, it meant shame.
I felt shame about the amount of equity I had after all those years working there.
I felt shame that my husband and I had to pull money from his 401(k) (I didn’t even have a 401(k) because startups) to exercise it in the first place because asking us to come up with $10,000 to purchase my equity at the time felt like asking us to come up with $1,000,000 cash. We had two young kids, and I was making $27,000 a year.
I felt shame about the amount I ultimately received.
I felt shame that when I asked for more years ago, they didn’t give it to me.
I felt shame that somewhere along the way I had convinced myself that one day this would all make sense financially.
I felt shame that I am still in the same position today, fighting for more equity at a new startup.
I felt shame that I allowed myself to be valued that way.
I felt shame that I valued myself that way.
I felt shame that I compared myself to people who received more.
I felt shame that I cared.
I felt shame that I knew better.
I felt shame that I used to idolize a woman who lived on our street in a mansion because she was Warren Buffets’s assistant and created generational wealth for her family through her equity.
I felt shame because my husband never made me feel bad about it, and I still felt bad anyway.
I felt shame that I had big dreams for what I would do with that money someday.
I felt shame that after all these years, part of me still viewed the outcome as a reflection of my worth.
I felt shame because I interpreted the outcome as evidence that I wasn't worth more.
I felt shame that after all the years of struggling, crying, and yelling, I stayed because I thought it would financially be worth it someday.
Because if I’m being honest, I didn’t just think the equity would be nice someday. I thought it would save us. Not in a literal sense. But in the way people tell themselves stories. I thought one day there would be a moment where all the hard parts made sense.
The answering emails at 3am while I was breastfeeding my newborn.
The going back to work 4 weeks after having a c-section when I was still bleeding from my incision.
The anger.
The stress.
The sacrifices.
The years of wondering whether staying was the right decision.
The years I stood outside the elevator on the first floor dreading to take it up to the office.
The days I wanted to quit.
The years I stayed anyway.
Because someday there would be an outcome.
Someday it would all be worth it.
Then someday arrived.
And the money wasn’t worth it.
The reality is that I was an assistant at a startup that wasn’t profitable at the time. Of course I understand why things happened the way they happened. I don’t blame anyone or anything. I get it. As someone who now helps make compensation and equity decisions, I would probably make many of the same choices myself.
I get it.
I genuinely do.
But understanding the logic doesn’t erase the reality of living it.
The strange thing is that none of this changes how I feel about the people.
The people are still the best part of the story.
The people from that chapter of my life are still some of my foundational people today. They’re the people I call when something amazing happens. They’re the people I call when something terrible happens. They’re the people who have helped me get jobs. The people who cheer for me. The people who knew me before I became who I am now. The people I would show up for in a moment’s notice.
The friendships outlasted the cap table.
And maybe that’s why this feeling is so complicated.
Because so many things can be true at once.
You can love an experience and still feel disappointed by the outcome.
You can love people and still wish they had valued you differently.
You can be happy for those who did well and sad that you didn’t.
You can feel grateful and resentful.
You can feel proud and embarrassed.
You can be angry and still enjoy the Prada shoes it bought you.
But to be fair, I did make money.
Just not the FU money that my 24-year-old brain hoped for.
Both things can be true.
But it gave me friendships that have lasted nearly two decades. It gave me opportunities I never would have had otherwise. (Seriously, I wouldn’t have gotten the 3 jobs I’ve had since that company if it weren’t for that job).
It gave me stories.
It gave me confidence.
It gave me a career.
It gave me my people in this world.
And those things have turned out to be worth more than I understood at the time.
The hardest part wasn’t the number.
The hardest part was realizing how much meaning I had attached to the number.
But the more I sat with it, the more I realized the shame wasn’t traveling alone.
There was grief, too.
Grief for the future I thought was waiting for me. Grief for the story I had been telling myself for years. The story where all the sacrifices eventually made sense. The story where staying would someday be rewarded. The story where there would be a moment when I could point to the outcome and say:
See? It was worth it.
I was worth it.
I wasn’t grieving the money as much as I was grieving the life I thought the money represented.
The version of me who finally got to exhale.
The version of me who got to point to all those years and say, “See? I was right.”
The validation.
The proof that I had been right to stay.
How many times I had told myself:
Someday this will all make sense.
Someday this will make up for the sacrifices.
Someday this will prove I was worth betting on.
But equity was never supposed to carry all that weight.
It was a financial outcome.
And I turned it into a verdict.
Those are not the same thing. The number is what it is. The relationships are still mine. The lessons are still mine. The growth is still mine. The memories are still mine. The life I built afterward is still mine.
The number doesn’t get authority over any of those things.
Because the truth about equity isn’t that it’s meaningless.
It’s that it’s incomplete.
It can tell you what someone was willing to pay.
It can tell you how a company valued a role at a particular moment in time.
It can tell you what happened financially.
But it cannot tell you who you are.
And for a very long time, I thought it could.
The number wasn’t the thing that broke my heart.
The story I attached to it was.
Very relatable read for many of us who've worked in tech during the hype and are rebuilding now. Thank you!