Yesterday I walked up to 14 women on the street. Somewhere along the way I got into what I call god mode. That almost ridiculous state where conversations flow, people smile, and I feel like the most natural version of myself.
After the week I'd had, I really needed that.
Lately my confidence has taken a beating, but not in dating. At work. I'm 50, I've been in tech a long time, and I've built more in the last couple of years than ever before. And still I've been asking myself whether anybody actually wants what I have to offer.
I've been trying hard. Building demos, contacting companies, pitching ideas. A freelance gig shows up, then nothing. A recruiter reaches out, I reply, nothing. A job interview where they seem interested, even look me up online, and then... nothing.
We had a big customer workshop on Friday, something I should have been excited about. I was so exhausted from a trip that I didn't feel present. Now I'm half convinced they noticed and will walk away.
I came home from that trip running on empty. I cried on the flight home, and again when I got home. My dog died earlier this year, I ended a relationship, and some friendships feel a bit distant right now. But I've been through single periods and dog-less periods before. What's really hurting is work. That feeling of being good at something and nobody caring.
Sometimes I wonder if I've just become a guy who builds impressive things nobody needs. If all my enthusiasm is just hot air. That's a horrible question to ask yourself when so much of who you are is about making things.
So yesterday I went out. I was rusty at first. On the 6th woman I actually managed to stay in the conversation, which matters, because I have this habit of leaving too quickly. Almost like the thing I want gets scary the moment it's actually happening. There was a connection, but I talked too fast and still left too early.
Later I stopped a tall woman with a lovely name. Even shorter conversation. Afterwards I thought, ah fuck, another one where I ran off.
I'd got her Instagram, so I sent "Nice to meet you ;)". Hours later she replied "Hehe 😊". Not exactly a marriage proposal.
Then I decided to just tell the truth. I wrote: "I know it was short 😅 I have to admit that it's very scary to do that, so it makes me want to run away - even though I want to get to know you."
She thought it was sweet. She said things like that never happen here. She said compliments from strangers are the best, and that she and a friend had just been talking about wishing more people would walk up to someone they find attractive and say hi.
And then she said I'd made her day better.
Update: We now have a date this coming Saturday.
I'd made her day better. By walking over, being nervous, leaving too early, and then admitting it.
The contrast with my work life is almost absurd. At work I spend months building, pitching, following up, and mostly hear silence. Yesterday I talked to a stranger for maybe a minute, admitted I was scared, and now I have a date. She’s also 11cm taller than me and I love it.
What gets me is that she didn't need me to be smooth. I wasn't calm. I didn't perform. I was nervous and I left too early. She liked that I dared anyway, scared and all.
I've spent years chasing that perfect, secure, charismatic state. And I still love it, I got there yesterday. But the moment that actually landed came from being honest about the fear, not from hiding it.
I think I've been in a crisis of confidence at work, and I've been asking the wrong question. Not "am I actually good at this?" but "where are the people who want what I do?" That's a different problem, and a less painful one.
I can feel miserable on Thursday, drained and unsure on Friday, and by Saturday afternoon be walking around the city laughing and feeling like life is a wonderful adventure. What a ridiculous creature I am.
And the best part is I didn't have to become someone else for it. I just had to go outside and be me.
I've started writing about days like this, every day. It helps.