As Christmas Nears, Remember to Prepare — and Reflect

A Christmas tree outside covered in show with a snowflake ornament hanging from a branch

If the weather isn’t enough of a sign that Christmas is approaching, the Hallmark specials and holiday shopping commercials surely make it hard to ignore. At the Cutter household, we’re especially enjoying the television line-up. While my kids gravitate to Rudolph or the Muppet’s Christmas, I can watch It’s a Wonderful Life every year and enjoy it just as much each time. The tree and decorations have been up for weeks, I’ve got my shopping done, and the girls’ winter break from school has started. This means we’ve had more time together to enjoy the anticipation of Christmas day. But personally, I’m also taking time this month to pause and reflect on the important things around me.

This week I want to shake it up a bit.  Instead of diving into a topic about finances, this week I’d like to instead use our time together to contemplate the joys of the season to maybe help us experience more meaning than just the inevitable gifts and good food. As Winston Churchill once said, “Christmas is a season not only of rejoicing but of reflection”. And he was a pretty smart guy.

After all, for most of us, when we recall Christmas of our past, we often find that our fondest memories are the simplest things. Not the nice presents or decadent food, but the memories. Spending time with family. Being thankful to God Almighty for all that we have and especially for the birth of his Son. Laughing, singing, listening to Christmas music. It’s the traditions and love that I remember and value the most. I see my wife, Jill, and daughters, Maeve, Phoebe, and Sophie, as the greatest gifts I have and I’m ever thankful for their presence in my life, their health, and the love and satisfaction they offer.

And you know, I am a lucky guy because I also have a wonderful work family as well.  Bonnie, Sheri, Jen, Allison, and Jill make it an absolute pleasure to go to work.  Their work ethic, morals, dedication, and friendship are something I truly value and am so thankful for them to be in my life.

So, let’s practice an exercise in reflection. What better time to evaluate what happened over this past year and how I can use that information to make next year even more successful? For example, here are a few questions I like to consider: 

– What’s the most important goal that I achieved this year?

– What’s the biggest mistake I made this year, and what did I learn from it?

– What is my best memory of the year, and why?

– What’s one thing I bought this year that I regret?

– Who’s someone I truly enjoyed spending time with this year, and can I do it again?

– What is the nicest thing that someone did for me this past year?

– What was my biggest time waster this year?

– If I could change one thing about the past year, what would it be?

– Did I grow spiritually?

– What are three words that would sum up this year?

Folks, these are just a few of so many things to consider as we look back on 2021. Rather than focusing on things we can’t control, like COVID and its variants, politics, government policies and spending, and more – this is the time of year to look inward. Taking time to ponder the events of the year and being grateful for all that we have can reap benefits that last well into the New Year. It’s easy to get caught up in all of the chaos of Christmas – the parties, the shopping, the rush to get everything done while simultaneously juggling your career and family can be exhausting. Hey, I get it.  But you know, carving out time to think and reflect reminds us what Christmas is all about and sets the stage for a more meaningful 2022.

As someone once said, “May you never be too grown up to search the skies on Christmas Eve.” The true spirit of Christmas is in our hearts and minds, not under the tree. 

If you’d like to read more about budgeting for Christmas, or retirement, you can take a look at last years’ post How Much to Invest for Retirement – or Christmas

So as always – be vigilant and stay alert, because you deserve more!

Have a great week and a very Merry Christmas.

Jeff Cutter, CPA/PFS is President of Cutter Financial Group, LLC, an SEC Registered Investment Advisor with offices in Falmouth, Duxbury, and Mansfield, MA. Insurance offered through its affiliate, CutterInsure, Inc. We do not offer tax or legal advice. Jeff can be reached  at

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