Dave Kashen explains how reframing taxes as a choice rather than an obligation reduced his stress around them. He connects this mindset shift to founders who resist necessary tasks like fundraising, arguing that seeing them as choices with consequences changes how you approach them.
Every year around tax time, I would be like, oh God, I got to prepare my taxes. You know, I had a tax accounting firm, but I still have to do like the prep to, you know, give them the information. And I made— you know, I was so grumpy, you know, poor— my poor wife and kids. Like, right around that time, I get so grumpy, and I'd sit down and I'd do it, and I'd be like, um, and then a few things happened. One, I had a coach who said, you know, you don't actually have to do your taxes. I was like, oh, like I thought, you know, death and taxes, right? Aren't like those the two mandatory obligations? And she's like, no, you actually don't have to do your taxes. There's just consequences. You know, you might pay fines, you might go to jail. I was like, okay, that's like, that's interesting. And so first it was this notion of it being an obligation. Like anything we do from obligation, we automatically resist. It automatically is like less energized. Or drains our energy. So I let go of seeing it as an obligation, and then I think that helped me just let go of resisting it. I was like, okay, I'm choosing to do it because I, I don't want to pay taxes or go to jail, and I like living here in the United States of America. So, um, I just, I just chose to let go of resisting it, and it was wild. Like, it was just no big deal. I'll just sit down and spent a couple of hours and, you know, do the things I needed to do. And so for me, that was like a great example. And I see this with founders all the time. There's a whole bunch of things that are just part of building a startup that, you know, founders are like, ah, I don't want to, you know, I don't want to do this part, but I have to. Oh, fundraising. Oh, I have to do fundraising, right? Like it's this big obligation. It's like, well, you don't have to do fundraising. It's just if you want capital to grow your business, then, you know, asking other people for it is part of the deal.
