She Keeps Taking My Calls. I Still Don't Have The Job.

What two years of quarterly check-ins taught me about doing the hard, unglamorous parts of work — in recruiting, in interviews, and everywhere else no one's watching.

Every quarter, I call the Head of Talent at a top-tier VC firm.

Every quarter, she says some version of the same thing: “Nice to catch up with you, Ben. I’ll let you know when one of our portcos needs recruiting help.”

That’s been the answer for two years. Two years of quarterly calls. Zero placements.

Here’s the part that should bother me and doesn’t: she always picks up.

Either she genuinely likes hearing from me, or she really doesn’t have work for us — honestly, I can’t tell which. (I do send her Sumato Coffee sometimes. Make of that what you will.)

But if she couldn’t stand these calls, she’d stop taking them. Nobody keeps a standing quarterly call with someone they’re trying to avoid.

That’s when it hit me: the hard part of hard work isn’t the effort. It’s staying alert enough, for long enough, that you don’t start resenting the process.

Anyone can push hard for a week. A sales cycle that pays off in year two requires something different — showing up quarter after quarter with nothing to show for it, and staying genuinely useful and pleasant the entire time. Most people don’t quit hard work because it’s hard. They quit because they get bored or bitter, and it shows.

We see the same pattern from the other side of the desk. Candidates get frustrated with long interview loops and case studies — understandably. Multiple rounds, a project you build for free, and you still might not get the job. That’s real, and it’s fair to be annoyed by it.

Here’s the test I’d give you, though: if you can’t get genuinely curious about the problem, the panel, or the product somewhere in that process, that’s information. Not a reason to phone it in — a reason to ask whether this is the right job at all. Better to find out in round three than eighteen months in.

If you’re building a business or a team, the unglamorous, repeatable stuff is the job. Recruiters: do your sourcing on the days you don’t feel like it. You’ll enjoy lunch more. If you’re building a brand, tell your CRO exactly what you’re doing and brace for the pushback. Choose the hard version on purpose. Sometimes that’s as small as making the bed or picking up after the dog when you’d rather not. Same muscle, smaller rep.

If you’re interviewing right now: a long process isn’t automatically a red flag, and your frustration with it isn’t proof the company is broken. But how curious you stay through it tells you something real about whether you actually want the job. Pay attention to that signal instead of pushing through on autopilot.

If you’re wrestling with a search that’s dragging — on either side of the table — hit reply. I’d rather compare notes than send you another bag of coffee.