Believing in the Plan

I hate spending money. Some genetic combination of Scottish, Dutch, and a Depression-era family upbringing turned me into someone who gets anxious just walking up to a cash register. Some people call shopping retail therapy. It’s never once been that for me. Every purchase kicks off an internal debate about whether I actually need it, and that internal chatter slows my decisions down, skews relentlessly negative, and keeps me up at night.

Eventually I got tired of feeling guilty and anxious about something that happens almost every single day. It was exhausting, and I couldn’t keep doing it to myself.

What actually changed things wasn’t much. I just made a decision: start believing in my own spending plan.

I’d always been something of a spending-plan fanatic. Every month, for years, I tracked everything I spent in a spreadsheet. A couple of times a year I’d review it and adjust the plan for the year ahead. It only took about two hours a month, less onerous than it sounds.

But despite years of tracking, I’d never actually bought into the process. I never went back and checked whether a prior year’s plan bore any resemblance to what I’d actually spent. I never looked critically at whether the plan reflected what I genuinely wanted to spend on. I rarely came close to spending what the plan projected anyway. I did it because a financially responsible person was supposed to. I still agonized over every purchase and still felt terrible making them. The plan wasn’t doing anything for me except eating up my time to build it.

So I decided I wanted two things: to stop feeling guilty, and to actually get some use out of the plan I’d already built. To get there, I sat down and really looked at what the plan actually said.

It turned out my spending plan was a fairly accurate reflection of my own values, built up over years of the choices I’d actually made. I don’t spend easily, so if something showed up in my tracking spreadsheet, it meant I’d believed in it enough to spend on it in the first place. My spending stayed remarkably consistent year over year, and I’d built in a cushion for the unexpected. And critically, I always had enough coming in to cover what was going out.

Once I saw that clearly, the logic followed: if something’s in the plan, it’s fine to spend on it. Even the unexpected stuff, because the cushion exists precisely for that. All of it, allowed, without the guilt attached.

This shift has taken time, and I’m not fully cured of the guilt even now. I still don’t love spending money, but it no longer stalls my decisions or eats up days of anxiety, most of the time. September used to be brutal for me, business expenses landing all at once, plus the usual pile of kid-related costs, after-school activities, hot lunches, school fees. Before I trusted the plan, I would have spiralled over all of it for days, second-guessed the whole decision to run my own business, maybe even considered shutting it down. All my energy would’ve gone into stopping the bleeding instead of actually moving forward.

This time, when the bills landed, I felt a little icky, grumbled about the cost of running a business, same as always, but then reminded myself: this is in the plan. It’s allowed. I’m not going to make myself feel bad about paying for professional liability insurance.

If you carry your own money anxiety, tracking your spending and building an actual plan is still the best remedy I know. Without one, every purchase becomes its own little interrogation. With one, you get to move through your spending with something closer to clarity.