My secret phone call with Hamish

On Thursday, my friend Hamish and I did a livestream for the MegaMaker community.

We had a great chat, where we explored his engineering work at Buffer, and what brought him there.

When it was over, we said goodbye to the folks watching and turned our webcams off.

But we kept talking.

And we did what people naturally do when they're not performing.

We spoke honestly about our life and work.

We shared our insecurities.

We revealed things we hadn't talked about openly.

And at the end, I realized Skype had been recording our audio.

"This got deep," I said, "should we release this as a podcast?"

"I think we should!" Hamish replied.

So here it is. My phone call with Hamish:

Short transcript:

Here's one of my favorite parts, where Hamish pointed out something unique about being in tech:


We can do so much too; that's the thing. If your job even touches tech, you have this pandora's box of options. I have friends who are electricians, and they can be... electricians. And that's it! But if you're in tech you can learn to code, you can learn to design, and you can consult, or you can build a startup. It's overwhelming!​


You just articulated it so well: tech gives us this constant paradox of choice: "I could stay and work on this or I could go over here and work on that!" And there's also this terrible FOMO: " Look at that person and what they're doing! Look at their success!" It's like I'm constantly evaluating ten parallel universes, thinking: "What if I'd gone that way?"​

If you like this episode, please share it! If you want more honest conversation about bootstrapping, sign up for my newsletter below.

Justin Jackson

Published on November 23rd, 2018
Home About Articles Newsletter MegaMaker
Powered by Statamic