OVercoming Spending Guilt

If there's one thing I've learned in nearly a decade of coaching people with their spending habits, it's this: money is as emotional as it is logical. We like to think it's all about the numbers, but it's tangled up in feelings—especially guilt. Most of us carry guilt around how we spend or manage money, whether from feeling like we don't have enough, regretting past purchases, or comparing ourselves to others. But today, I want to talk about a mindset shift: a way to break the guilt cycle and replace it with a more empowering cycle of planning, spending, and reflecting.
This guilt often comes from the spend > track > regret cycle. It's when we make a purchase in the moment, track it after the fact, and only then realize it wasn’t the best choice. We didn’t plan for it, and now we regret it. Maybe we saw something we wanted (or felt like we needed) and bought it impulsively. Then we have something more important come up that needs to be paid for. We realize we already spent the money. Then we regret the spending. Or it may look like seeing something we need or want, spending the money, later realizing the item could have cost less elsewhere if we had done our research, then we regret and feel guilt about the spending.
One of the biggest ones my husband and I experienced was with a water softener. Just after our first child was born, we had a water softener salesman show up at our door. Being young and still not very experienced with door to door salesmen, we let him in. He used our new baby to tug on our heartstrings and we agreed to do a whole house system with a water softener and RO water spout in the kitchen. When all was said and done, we went to Lowes and found out that we could have gotten the same things for a quarter of the price. Boy did we feel stupid! We still look back and regret that one, but we’ve had to learn to let it go. That’s when we realized: spending guilt and frustration can cloud our judgment, making us doubt ourselves. But practicing self-compassion, even after mistakes, helps break that cycle.
The water softener example was a large one, but we have had many such regretful spending moments over the years. We had a lot of shame over going into overdraft each month, asking family for a loan, and much more. Over time, with a lot of trial and error, we learned there is a better cycle to be in. The plan > spend > reflect cycle.
With this cycle, we plan our spending BEFORE we spend. We think of all the things we need our money to do for us - going beyond just the day to day, monthly spending. We plan for things like Christmas, car registrations, school fees, and yearly subscriptions year round - not just before they happen. We plan on emergencies or other unexpected things happening. We even have a plan for our kids' weddings before any of them are even close to being married.
Making this plan, having it all laid out in front of us, helps us spend with confidence. We know we can buy that pizza or pay for that car repair and still be able to pay for all of our other expenses - because we have it all planned out. Now, don't get me wrong, we were not planning on weddings and the like right off the bat, but we stuck with what we knew we needed now and in the near future. As more and more things got funded, we were able to expand to include more things in our spending plan. The key difference here is that with the plan > spend > reflect cycle, your spending aligns with what matters most to you—because you planned for it ahead of time. Instead of reacting and regretting, you're in control, making intentional choices that align with your goals. And that’s what takes guilt out of the equation. If we had been following this plan back with that door to door salesman, we would have known that it wasn't part of our plan. We could have updated our plan to include it, done our research, and done it much more cheaply and intentionaly when we were actually ready for that expense.
After we spend, we can reflect on our purchases and not have that same feeling of guilt and shame. Reflection doesn’t mean beating yourself up over past choices. It’s about learning from them and making tweaks to your plan so that you can get even closer to your goals next time. If something didn’t go as planned, adjust and move forward. This is all part of the process.
If you really want to kick spending guilt to the curb, start today by giving every dollar a job. Plan for each dollar, track your spending, and make sure it lines up with that plan. After a week or so of spending, look back. Is your spending in line with what's important to you? If it is, keep going. If it's not, adjust, re-plan, and keep going. Remember, no one taught you how to do this. You can't magically know something you were never taught. You'e got this!