• RSL = Retired school leader
  • DH = Dear husband

A great party

I went to a retirement party Friday night (not the one featured above, but it was about that size), and it was one of those times when I was struck by how lucky I am to work where I do. I’m a teacher with a job in the library of a very multi-cultural, inner-city high school, and I’ve known since the moment I set foot in it that I wanted to spend the rest of my career there. I believe it all stems from the students, for many of whom the school is like a second home, but it definitely extends to the staff. In no other situation have I ever worked with such a supportive, encouraging, authentic group of people. Staff have come and gone over the years, but the work culture of our school is long-established, and it doesn’t alter with a changing cast of characters.

The party Friday night was filled with the familiar faces of former colleagues – teachers, technicians, office staff, department heads, custodians, vice-principals, principals – some whose career paths have moved them to different schools and others who are in retirement. It was just a fabulous event, and it thoroughly honoured the retiree in question – who was completely surprised by it.


When one of the “V.I.P.” guests arrived – one of the few who would be giving a speech – there was a widespread “Oh, look who’s here!” response among many – including me. I knew I’d have to wait my turn to have the chance to chat with this person – I’ll call her RSL for “Retired School Leader” – because she would be approached by a steady stream of friends. By this point in my career, I’ve worked with many different school administrators – that is, principals and vice-principals – and three stand out in my mind as being exceptional – as being true leaders who have served both staff and students with vision and passion. RSL is one of them.

I was surprised when, after a warm hug and “Hello!”, RSL asked if she would be able to talk with me. “Of course!” I said, and we found a table out of the way. “Do you remember when you and your husband started to make an effort to get out of debt?” she asked me. I nodded a yes. “Well, that’s a goal I have now too.” For the next several minutes, I listened as she described her circumstances. She’s actually in a strong position overall – but with more debt than she’d like to have included in the equation. I asked about different options, and she welcomed my questions, answering in detail. Although I have grown more and more comfortable talking about personal finances with different people (to the extent that I have had to learn to hold back and filter what I say), I’m aware that for most people, open and frank discussions about money are rare, if not non-existent.

Stepping into a vision

Soon, others came to our table, as I knew they would, to have their chance to talk with RSL. We established that she’d keep me posted, and our conversation ended. I felt so touched to have been sought out by her in this way. It wasn’t the first time a colleague had talked to me about personal finances. Several staff members and even some students know about my quest to become completely debt-free, and on occasion, one will stop by to talk about a success, a stress, or an uncertainty in money management. One fellow teacher recently came to the library and asked me, “Can I borrow that life-changing book?” I didn’t know what he was talking about, but it was the Dave Ramsey book that has guided us on our journey out of debt, The Total Money Makeover (Canadians, choose this link for the book.) I was happy to lend it to him. I love being that person.

I think in the case of RSL, I felt a particular honour in having been approached for this talk because there was a reversal of roles involved. When we had worked together, I was the one seeking guidance from her – whether about a certain student or the ins and outs of scheduling an event – and here she was, reaching out to me for support, as someone who understood the pursuit of stronger finances that she had taken on.

In the very first post I wrote for this site, two weeks before our journey out of debt began in June of 2012, I lamented the vision I’d had in my youth of my older self. “We’re in a position now that’s so different from the one I envisioned as a young woman.  I imagined that we’d coast through our 50s with the ease of prosperity, the satisfaction of well-established careers, and the dignity of being in a position to give back to our church and community.  Instead, we are financially tight, putting a lot of time and effort into making DH’s new career succeed, giving very little in terms of time and money.  And we’re in debt.  Far too much debt for people our age.” I believe now that my talk with RSL Friday night awakened me to the welcome realization that I’ve been stepping into that lamented vision. It’s not that I’m living the life I described. After all, we’re still financially tight, and we’re still time-strapped on a day to day basis. But I am, as it turns out, in a position to give in a significant way.

I’m not giving as much money as I hope to, but I’m giving my alliance to people who have had a wake-up call in their finances. And although financial advice comes at us all from every angle, not everyone has a financial confidant – a safe person who gets it. Again, I love being that person.

I remember a pastor once saying, “Your point of greatest weakness will be your point of ministry.” I was definitely very weak in managing money – right from my teen years when I’d whine and beg my parents to give me an advance on my monthly allowance because I regularly drained it by mid-month. Now, as I get stronger, I’m so glad to be a support to other people who are also trying to turn things around. “We’re in a position now that’s so different from the one I envisioned as a young woman,” I lamented as we approached the starting line of our journey out of debt. But I don’t lament it anymore. Because it’s developed into something rich.

Have you ever experienced the phenomenon of a weakness turning into a strength? Do you ever have open and frank conversations about personal finances with the people in your life? Your comments are welcome.

*Image courtesy of Tony Webster


Join the Conversation


  1. I love being able to look back and see how far we’ve all come, and I think it’s really cool people are coming to you for advice. To answer your question: big time yes! My blog essentially…well not even essentially, but directly led me to this current job I have which is not only what I love doing (making personal finance videos), but also pays me way more than any other job I’ve had. So yup! 🙂

    1. I love hearing this from you, Tonya! It will be SO interesting seeing how you manage abundance. How wonderful that your blog, in which you have always been transparent – including points of vulnerability, has been a direct link to your current strong position! I love it when things work out like that!

  2. “I think in the case of RSL, I felt a particular honour in having been approached for this talk because there was a reversal of roles involved” This is so great that you are viewed as the expert. A go to person when other need help. I think I have had a similar turnaround when it comes to personal finance. It was a weakness for us for many years, something we would never talk about or share with anyone. Now I openly talk money and have helped others gain control and it’s a great feeling.

    1. Thanks, Brian. It really is liberating to be able to discuss money matters openly. It’s a very significant part of life – too significant to be all hush-hush about. I think the fact that you and I both have a history of poor financial management makes us particularly approachable. I like it when something good comes out of a struggle!

    1. Kay, it’s so good to hear from you again! I think I’m a mentor in the sense that I’m a safe person to talk to – open and nonjudgmental when it comes to money talk. My “expertise” is extremely basic, but that actually seems to be enough. Thanks for commenting, my friend : )

  3. Probably none of our lives have turned out just as we envisioned in our younger years. I can look back now and see how failure and weakness have shaped me in really valuable ways, and how that has increased my ability to help others and show compassion instead of judgment.

    1. I think it’s possible to be held hostage to a vision. So much better to let it go – because there just might be a better vision to replace it : )

  4. I definitely shy away from talking about personal finance with people. I tend to be kind of judgmental, so I don’t want to alienate people if I react strongly to how they got in debt or whatever. I think I’ve gotten better about that, but still…

    Then again, I usually just say I’m a blogger. I don’t actually say what the subject is, I think.

    I’m glad you’ve been able to offer some guidance to people who apparently really need it.

    1. I always like your honesty, Abigail! As for finding yourself reacting with judgment to people’s financial mistakes, is it possible to consider an area where you struggle, and then extend that understanding to this area of struggle (that so many have) – even though it’s not yours? For instance, I have a friend who is great with money, but not so great in regulating her food intake. She is able to be compassionate about people’s money problems because she gets it – through her issues with food. I hope that makes sense!

  5. While some people have reached out to me for personal finance advice, I think those “frank” conversations haven’t really happened much. I think it takes a tremendous amount of trust – from both sides – to have those conversations. I hope they start happening because it’s typically the first step towards having a better financial future.

    1. I hope that they start happening for you, DC. Clearly, you have a lot of good advice to pass along. In my case, I think that the fact I’ve had to turn from my own unhealthy habits in managing personal finances – and I’m open about that fact – helps people to trust me. There’s a lot of fear, pride, defensiveness, shame, and simple awkwardness out there surrounding personal finances. Do you talk with people face-to-face about your blog at all? I can’t help but think that would be an opener for some to speak to you frankly about their money issues.

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