Eight years in, a lot of the shop runs on autopilot. Inventory, restocking, vendor relationships, the rhythm of a Tuesday morning vs. a Saturday afternoon. I don't think about most of it consciously anymore. That's the part that gets easier.
Here's what's still hard.
1. Saying no to a customer. After eight years of trying to say yes to everyone, the no's still feel like failures. A customer asks if I can hold a boot for him for two weeks and I have to tell him I can't because I have one in his size and I can't promise it won't sell. He's annoyed. I'm annoyed. The math is right but the relationship took a small hit. I never get used to those moments.
2. Inventory bets in November. Every fall I have to commit to insulated boots, parkas, and bibs based on what I think the winter will be. If I overbuy and the winter is mild, I'm sitting on $30K of insulated bibs in March that I'll have to clear at a loss. If I underbuy and the winter is brutal, I'm out of stock by January 15 and watching customers walk to other stores. Eight years of doing this and I've gotten the inventory bet right maybe four times. The other four times I was either too aggressive or too conservative. There's no fix for this. The weather is the weather.
3. Hiring. I've had four employees over the years. Two were great. Two weren't. I still don't have a reliable interview process. I trust my gut and my gut is right about 50% of the time, which is not a great hit rate. The good ones figured out the boot-fitting in three months and stayed for years. The bad ones never figured it out and I should have let them go faster than I did. Letting people go is also still hard.
"After eight years, I thought I'd have answers. I have habits. There's a difference."
4. The end of summer. Every August I have a stretch of two or three weeks where business slows down — guys are on vacation, contractors are between jobs, the back-to-school noise dominates the news cycle. The shop gets quiet. Eight years and I still get nervous in that stretch. Logically I know September is going to fix it. Emotionally, I'm convinced every year that this is the August where the business doesn't come back. It always comes back. I always worry anyway.
5. Knowing when to take a day. I work most days. I tell myself I'll take a day this week and then I don't, because there's always inventory to organize, a customer who needs me, a vendor on the phone, an account to settle. The shop runs better when I'm in it. The me-running-the-shop runs worse when I'm in it constantly. I haven't solved this.
6. Watching customers age out. I've had a few customers retire in the last two years. Guys I've sold boots to for seven years. They come in to say goodbye, tell me about their plans, walk out, and don't come back. Some of them I genuinely miss. The relationship was real. Then the relationship is over because the work is over. I haven't figured out how to feel about that.
7. The fact that I'm still figuring it out. After eight years, I thought I'd have answers. I have processes that work, brands that sell, and customers who keep coming back. I don't have answers. I have habits. There's a difference. The habits are good. The answers I'm still working on.
If you're earlier in this than I am, none of this should discourage you. The hard parts being still hard is fine. They're hard because they're the parts that matter. The easy parts run themselves and don't teach you anything. The hard parts are where the eight years actually went.