When tough conversations hit close to home

Nobody said it would be easy.

At some point, we’ve all heard those words in response to a conflict or struggle we were going through. In my case, I said it to myself because there wasn’t anyone to talk to as I was wrestling with the wreckage from a really tough conversation I had with someone dear to me.

For those who’ve been around for a while, you know we have a pretty firm point of view about money, careers and happiness. It’s one that is rooted in a simple idea.

If you spend your time on the things that mattered most to you, and spend your money on things that give you more time, then you’ll have more time to do the things that actually make you happy.

It’s not rocket science but can very difficult to put into practice. Our pursuit of Financial Independence has helped us design a life that does just that. We prioritize our values over consumerism, career aspirations and the carrying on of outdated practices that hinder our financial progress.

We knew sharing our story would rub some people the wrong way but we were willing to deal with the collateral damage. That is, until we were staring that wreckage head on. And instead of mangled and twisted metal, it was the crumpled up faces of people we love.

When you’re in your 30s, careers start to take off, families are built, routines are defined and a long list of responsibilities fall in your lap that create distance between you and the people you used to spend time with. It’s a struggle many young professionals deal with as they grapple with striving for more and the life they used to have. It’s especially difficult for those who have left home and are separated by oceans and time zones. But…

sometimes, the people you love can be a stones throw away in miles and on another planet in mindset. Click To Tweet

That’s the case here and it’s something, I’ve struggled with for a while. I’ve always been someone that strives for improvement. I have a mixed record having collected my fair share of failures over the years, but I believe the wins outweigh them all. Along the way, I’ve felt the friction between the direction I was going in and the people I was slowly losing contact with.

As I was going deeper into understanding the investment world, personal finance, entrepreneurship and real estate, many of the people I know were doubling down on work, upgrading their cars, and celebrating the purchase of their new homes. Others found themselves in different lanes and decided to go back to school under the belief it would unlock more doors in the future. So when I finally get a chance to catch up with someone I hadn’t seen in a while, I was looking forward to hearing what was new.

Somehow, this simple drop in spiraled into a tense discussion about our blog, our message and how it makes people feel. As I understand it, the feedback was that we should acknowledge there are people who want to pursue this lifestyle, but can’t for a variety of reasons. In general, I was fine with that feedback because I certainly understand that, yes, there are people who are unlikely to achieve financial independence. Hell, I used to be one of them!

But the feedback wasn’t what sent us down the rocky road; rather, it was the context of that feedback. To protect their identities, I won’t get into specifics, but in summary, a major life decision was made on their end and they admitted to feeling uncomfortable sharing the news with me because it has financial implications they believed I wouldn’t agree with. In a perfect world, they would’ve shared it with me months earlier but felt I would be judgmental of their decision.

It really hit me in the gut to hear that and reminded me that I have the tendency to let my passion spill into places where it may not be welcome. It was also yet another reminder of the role money plays in almost every aspect of our lives.

Money can be both a source of pride and shame, a measure of one's strength and at the root of one's weaknesses. It can be a reflection of insecurity or an amplifier of values. This makes it the perfect kindling for conflict. Click To Tweet

This short but uncomfortable interaction didn’t sit well with me at all. Here I was thinking they were just really busy, only to learn…they were avoiding me.

I’ve been been entrenched in the debt freedom and FIRE community for a while now so I know we are a passionate bunch. We’re quick to recommend books, apps, services, blogs, podcasts, articles and even documentaries. These are all well-intended attempts to help people get a little closer to the light and make better financial decisions.

So as I reflected on the past few years and how my relationship with this person had evolved, I had flashbacks of every single unsolicited ramble I’d ever made and realized they had every right to feel the way they did.

It was a tough pill to swallow because on one hand, we believe we have to hit hard to break through. In a world where people are bombarded with marketing, cultural and social pressures to spend more than they earn, if we were to try to make a difference in a subtle way, it would be far too easy to ignore.

On the other hand, there is a cost to being hard-hitting and in this case, one of our haymakers landed on someone we love. Hell, for all we know it’s landed on several people that just haven’t said anything.

So what’s the moral of this story? Well, Im not really sure.

I’m still processing it all because honestly, I don’t regret any of the things I may have said. My point-of-view is supported by data and the warning signs are all around us.

The average American is in about $130K in debt, the average student loan debt balance is about $30K and rising and the average credit card balance is just short of $7K. A record number of people with auto loans are behind on their payments and as home equity rises, there’s little reason to believe American’s won’t start borrowing against it. Health care is expensive and life expectancy in the US has declined for the last three years due to declines in health and the opiod crisis.

Most of the people I know are working to middle class and if they are anything like "the average American", they will be tomorrows working poor. Click To Tweet

All of this is compounded by increased pressure on publicly traded companies to outperform prior years, oftentimes leaving them with no choice but to make job cuts to boost profitability. This is a recipe for disaster and particularly for the people who don’t have a safety net, the next economic downturn will make an already waist deep hole even deeper. I don’t always agree with the man, but I do relate to why Dave Ramsey raises hell every now and then.

Here’s what I do know.

We make a concerted effort to present the benefits of FIRE, entrepreneurship and the importance of personal finance to anyone who will listen. We do this because we understand how devastating financial illiteracy can be. But more importantly, we know that not every financial struggle stems from someone not knowing better. Life just aint that cut and dry and we are not perfectly rational beings.

There are plenty of people who have the means, the tools, access and education that still make terrible financial decisions. THEY are who we focus on! Click To Tweet

We’re not nearly as concerned with the hard-working teacher who is strying to make ends meet while saving, cooks at home for all her meals and is hoping to take a vacation this year. Our beef is with the high salaried employee with little to no savings and a flawed assumption that they can always find another job.

We know they may appear to have it all together but as you zoom in, you can see cracks in the veneer and consequences looming in the background. A simple light tap on the shoulder isn’t going to get their attention so we sometimes opt for the heavy handed tactic to rattle them a bit.

While it’s effective, we now know that not everyone want’s to be or is asking to be awakened. Some people are perfectly fine with their decisions and while they know it isn’t perfect, they’re doing the best they can to get ahead. As we always do, we’ll continue to leave breadcrumbs and a roadmap behind so if/when they decide to get on board, they can benefit from our experience.


  1. Sorry to hear that it was such a rough conversation. I definitely get it. I think some of my ex-husband’s friends leaned not to talk about money around us because I was kind of judgmental. I did my best to hide it but they could see through it and I think it damaged our relationship to an extent. But in my defense these were people making heinously bad money choices over and over and kids were involved.

    At any rate, I think it’s good that your friend was able to be honest with you about his/her concerns so that you’re more aware for the future and anything that makes us stop and reassesss from time to time is a good thing too. However much it hurts initially.

    • Thank you so much. It feels like watching a train wreck in slow motion but I’ve got to learn to let people live their own lives and let it go.:(

  2. I know exactly where you are coming from. In the black community, those hard-hitting tactics often pushed people further away rather than help. And Im sure there is a deep rooted reason for the reaction. But the bread crumb tactic doesn’t seem to work either. Its a tough to care so much!

  3. Oh yes I know the feeling oh so well. In my working class family (and in-laws!) if you have your bills paid then anything else is gravy. But just this year alone there have been 5 hospitalizations of 3 family members, broken down cars, a new baby with unemployed parents, And a move to a trailer park. Of course people get sick and babies get born And people have to move but in every instance these things were preventable with a tiny bit of planning. The beef i have with my family and in laws is that their life choices WILL impact mine no matter how “selfish” I try to be. And investing love and energy (ain’t nobody asking for money from us!!) with people who will suck it all down just makes me and my husband feel like we are the suckers. This is hard with no easy answers

  4. I LOVE this article…mainly because this is exactly why I began getting so passionate about the psychology behind behavior change – there’s a book, Changing for Good by Prochaska that speaks to what people need in order to change – spoiler alert – it’s usually some dramatic event in their lives that push them to shift. Knowing you, having access to you and seeing you can be helpful, but their change really isn’t about. you at all. Anyway, thank you for this article!

Leave a Reply