Anna recently tweeted one of her archive posts that really resonated with me. It’s full of great tips on dealing with other people who may not really understand or accept your new commitment to money matters.

I can relate! By far one of the most difficult leadership challenges I’ve ever faced was trying to get my teenagers on board with the transition to a more frugal lifestyle. I’ve started a couple of businesses, and I can assure you that both times I instantly found myself living a new “spending less” lifestyle.

The first time, in 2001, was relatively easy. The only person I had to convince was my wife, and I already knew she was on board. Starting a new business is a little insane, but she married me — so I already knew she was a little insane. I couldn’t have done it without her support in many areas — frugal living being only one of them.

We had a toddler and a baby at the time. The baby didn’t care, and as long as the toddler could go outside and play in the dirt, she wasn’t worried, either. I’m pretty sure if we’d moved into a tent, they both would have been perfectly happy.

The company grew quickly, and it wasn’t long at all before we didn’t have to worry about how to pay the bills. Yay!

Fast forward to 2013.

I had found myself leading software development for a remote subsidiary of a large international corporation. I had plenty of things to worry about, but a paycheck wasn’t one of them. When the company decided to consolidate development within the main corporation, I started another company. No prob, we’re just living off of savings again for a while, I thought.

This time, however, my daughters were teenagers, and we had two more kids as well. I foolishly failed to realize at the outset that I’d need to get them on board. It seems so incredibly obvious in hindsight, but I guess at the time I might have figured they’d just blindly go along with whatever their mother and I came up with. (Hah! Like teenagers always do, right?)

One day early on, my 13-year-old daughter asked me one simple question and a realization hit me like a ton of bricks.

“Dad, are we poor?”

I had spent all of my time convincing everyone of what a truly amazing thing we had going — yet somehow I had neglected to convince the most important people in my life, living in my own home, that we were going to be at least basically OK.

“No, we’re not poor. But we should be living like we are poor.”

And of course the part I didn’t say: “…or we will be.”

I was fairly certain we’d be just fine no matter how things went with the new company. However, it turns out it’s remarkably difficult to share that vision with someone else whose entire life has been subject to some degree of lifestyle inflation. From the earliest time our 13-year-old could remember, throughout her entire existence, for each and every year, our financial situation had improved, and our lifestyle bit by bit along with it. I easily could see that as “luxury,” but now I only could expect my kids to see that as “normal.”

When Anna tweeted about getting others on board, I responded that, “One of the toughest leadership/parenting challenges I have ever faced was trying to get my teenagers on board.” She asked me how I did it.

The truthful, concise, answer is that I didn’t.

I could enumerate the dozen or so things that I tried. But there was certainly no magic bullet, and I get exactly zero leadership or parenting credit for merely attempting to get my teenagers on board. This story is by no means a tragedy, however. Of their own accord, they eventually accepted our circumstances. I believe that was because of the strength of their character and because they chose to do so when the situation rationally was weighed against the alternatives. It wasn’t easy.

There is a simple moral to this story, though — It is approximately 800 billion times (my estimate, your mileage may vary) easier to forego lifestyle inflation than it is to voluntarily implement lifestyle deflation. When you start making more income, save it — don’t spend it. Spending has inertia that is very hard to reverse.

Just saying ‘no’ — to yourself, to your teenagers, to whomever — is hard. Saying ‘no’ after you’ve already said ‘yes’ repeatedly is REALLY FREAKIN’ HARD, so make fun stuff like these 56 Things To Do Instead of Spending Money “normal” and make spending money the “luxury.”

Right this very second is the perfect time to start.

Have you struggled with trying to get others on board with your new “spending less” lifestyle? Or, have you managed to convince others to get on board with you? I’d love to hear how you did it.

Tim Johns has spent most of his career trying to make sense of data (spending and otherwise). He and his wife are the proud parents of four amazing kids with varying degrees of appreciation for frugal living. When not cursing at his computer, Tim usually can be “found” somewhere in the Cascade mountains of Western Washington either pretending he isn’t getting his own family lost, or searching for other lost hikers by headlamp as a Search and Rescue volunteer. You can follow Tim on Twitter @TimJohnsWA.