My Money Story

I grew up on the South Side of Chicago in a working-class family.  Labels are limiting, but you could call us blue collar at the start of our run, and middle class at the end.  In other words, my parents were fortunate enough to live through the post-WW II boom period in America, a prolific time that saw the building out of the suburbs, the interstate expressways, public housing (believe it or not, that was a huge achievement in the fifties and sixties), city infrastructure, bridges, sky scrapers, schools and universities, manufacturing plants, energy infrastructure, etc.  The steel industry and auto industry were booming.  It was almost impossible for an individual during that time not to get a decent job. 

Regarding my approach to money:  both my parents lived through the Great Depression.  I saw them work hard to provide for me and my three siblings.  My parents’ views rubbed off on me, and so my primary approach to managing my finances became “security.”  I need a reserve of savings and investments that I can draw from in case something goes south.  We all have our own stories, and so your relationship with money is likely different.  When I was young, I saw my dad sitting at his desk, sorting through bills, deep in thought with a furrowed brow.  My mother would drive to three different grocery stores and only buy what was on sale at each one.  I knew it was a struggle for them to send four kids to private schools and manage a household.  I saved my first communion money.  I saved what I could from my early jobs: washing ambulances, sanding cabinets in a cabinet shop, working as a laborer for a homebuilder, waiting tables at an Italian restaurant, and scraping and spraying the sides of buildings as a brick washer (yes, that’s a thing) for a masonry contractor.  And as soon as I got a job out of college, I started saving some of my earnings.  Don’t get me wrong: during my twenties I would NOT call myself “fiscally conservative.”  There were concerts, dinners out, nights with friends at the bars, road trips.  I enjoyed myself by all means.  But once I got a bit older, I got serious about getting my financial house in order.  Luckily, I have a spouse who is also “fiscally insightful” and understands the balance between spending and saving.

When it comes to spending, I am a big proponent of “value.”  I get frustrated when I spend money on something that does not bring me value.  The organizational guru Marie Kondo would use the phrase “spark joy.”  I do indeed always ask myself, “Does spending money on this spark joy?”  As a result, I can sometimes get a lot of satisfaction from spending a good bit of money on something I perceive as valuable (I’m looking at you my high-end, carbon frame road bike).  And sometimes I get very frustrated after spending just a small amount on something that was completely unsatisfying (yes, that last crappy meal at the hugely mediocre and loud local restaurant is coming to mind.)  

Each of us is on our own financial journey. Once in a while, it’s good to reflect on where you came from and where you are going.

As far as financial experience, I have been planning our retirement for the last 25 years.  Out of necessity I put together my own spreadsheets, visuals, dashboards, trend analysis, concepts, widgets, etc.   I am happy to share these all with you as part of my overall mission to improve the retirement outcomes for 10,000 people.    

On a personal level, my wife and I raised two kids and put them through college.  They are now both launched (with full-time jobs AND health insurance.  Woo Hoo!)  While doing the above, I served in a variety of roles with a “financial” theme, including in public accounting (I am a Certified Public Accountant, though I no longer practice as one), as a financial manager at a chemical company, a copywriter for a direct marketing creative agency that served the financial services industry, a content creator for a mutual fund company, and most recently as a product manager (software) for Morningstar, Inc.  I have created software tools from scratch that are still used by financial advisors to this day.  During that process, I learned what financial advisors do, and what investors need to do, to put together a solid retirement plan.  I consider myself a subject matter expert on what is required to set yourself up for retirement success.

Now It Is Your Turn

-Think through your story and try to sum up your relationship with money in a few words.  Write it down on your own, or fill in the blank:  “To me, money represents _________.” 

Some suggestions:   

“Money gives me security, money is good, money is bad, money is evil, money brings joy, money is stressful, money is useful, money shows my accomplishments, money brings satisfaction, money is the root of all evil, money makes the world go round, more money is better, more money is worse, less in more, more is better.  Money can’t buy happiness.  Money, money, money.  I am constantly stretching my money too thin.  Money is always just enough. I am usually scraping by.  Money is barely there. I never have enough money.  When I have money, it burns a hole in my pocket and I want to spend it. 

And my personal favorite, which I don’t necessarily agree with, but which stuck with me for a long time, courtesy of my boyhood friend Jack:  “Dollars are just units of fun.”  Do you agree that the more dollars you spend the more fun you have?  Or, do you agree that “the best things in life are free?” 

You get the idea.  Write down some of your earliest and/or most impactful memories about money, spending, and financial matters.   

Once you reflect on your past with money, and your current feelings about money, ask yourself some practical questions:

-How confident are you that you can make good financial decisions? 

-Do you have any financial goals in the short term and long term?  If so, write them down. 

-How much of your current spending do you think “sparks joy”?   How much of your spending is not giving you much satisfaction?

-In an ideal world, would you like to have a plan in place to help you get to a comfortable retirement?

-How much money are you willing to save now for your retirement in the future?    

Up Next: My Worst Investing Mistakes