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Is That Deductible? The Gift of Giving: Embracing Holiday Generosity with Intention

Dec 30, 2024

The holiday season is a time of joy, connection, and celebration. For many of us, it’s also a season filled with the complexities of gift-giving. The act of giving should ideally come from a heart of generosity, yet it often comes with its challenges—from finding the perfect gift to navigating differences in how we express and receive love.

In my household, this dynamic plays out in interesting ways. My wife thrives on the exchange of gifts. She loves the thoughtfulness behind each item, the joy of unwrapping a present, and the emotional connection it represents. I, on the other hand, am not someone who feels particularly energized by either giving or receiving gifts. It’s not that I don’t value generosity or thoughtfulness; it’s simply that my emotional tank is filled in other ways, such as meaningful conversations, shared experiences, and acts of service.

This disparity has led us to find creative ways to navigate the holiday season and ensure that gift-giving remains a joyful part of our family’s traditions. If you’ve ever struggled with the philosophy and practice of holiday giving, I hope my story will resonate with you and offer practical inspiration.

The Generous Spirit vs. the Practical Mindset

My wife is a pretty balanced combination of the 5 love languages, but gift-giving is definitely important to her. She lights up at the thought of finding the perfect gift for someone she loves and feels deeply appreciated when receiving a thoughtful present in return. For her, the holiday season is a chance to express love in tangible ways.

For me, gift-giving often feels more like a logistical puzzle than an emotional experience. I’m the type of person who, for the most part, already has what I need and want. As a result, it’s hard for me to come up with ideas for gifts—both for others and for myself. This disconnect has, at times, made holiday shopping feel like a chore rather than a celebration.

A Secret Santa Strategy

One way I’ve adapted to this difference is by enlisting help. Every year, I ask my youngest daughter, who shares my wife’s love for gifts, to act as my “Secret Santa.” She takes on the task of picking out thoughtful and personal gifts for my wife on my behalf. This arrangement has been a win-win: my daughter enjoys the process of shopping and gift selection, my wife receives presents she loves, and I feel relieved of the pressure to come up with perfect ideas.

This approach works well, but it’s not without its limitations. While my daughter does an excellent job, I’ve realized that I still want to make more personal contributions. This year, my wife and I have decided to try something new: a shared Google Doc where we can each add gift ideas for one another throughout the year. By keeping a running list, we hope to take some of the stress out of last-minute shopping and ensure that our gifts feel meaningful and intentional.

When You Have Everything You Need

One of the biggest challenges of gift-giving for someone like me is the feeling of already having everything I want or need. Over the years, I’ve realized that the best gifts aren’t necessarily things but experiences or gestures that add value to my life. For example, a heartfelt letter, a planned outing, or even a charitable donation made in my name can be deeply meaningful.

In fact, charitable giving has become a significant part of my holiday tradition. Every year, my sister and I make donations to charitable organizations in honor of each other. These gifts not only align with our values but also bring a sense of purpose and connection to the season. While not every gift can be tax-deductible, the act of giving to others—whether through time, resources, or money—reminds me of the true spirit of the holidays.

Practical Tips for Intentional Gift-Giving

If you find gift-giving to be more of a challenge than a joy, here are a few strategies that have helped me:

1. Embrace Collaboration

Don’t be afraid to enlist help. Whether it’s a family member who loves to shop or a shared Google Doc for brainstorming ideas, collaboration can take the pressure off and make the process more enjoyable.

2. Focus on Experiences

When material gifts feel unnecessary, consider giving experiences instead. Tickets to a concert, a cooking class, or a weekend getaway can create lasting memories and strengthen relationships.

3. Make It Personal

Even if you’re not a natural gift-giver, small personal touches can make a big difference. A handwritten note or a gift that reflects a shared memory shows thoughtfulness and care.

4. Give Back

Incorporate charitable giving into your holiday tradition. Donations to causes that matter to your loved ones can be deeply meaningful and align with the spirit of the season.

5. Plan Ahead

Start keeping track of gift ideas throughout the year. By the time the holidays roll around, you’ll already have a list of thoughtful options to choose from.

The Heart of Generosity

At its core, gift-giving isn’t about the material value of the gift but the thought and intention behind it. Whether you’re someone who loves the ritual of giving and receiving gifts or someone who struggles to find joy in the process, the key is to focus on generosity—both toward others and toward yourself.

For my wife and me, the act of navigating our differences in this area has deepened our understanding of each other. It’s a reminder that the holidays are not about perfection but about connection, compromise, and love.

Is That Deductible?

Sure, you could technically buy a business-deductible gift for your spouse—like that shiny new stapler the office desperately needs. Imagine the joy on their face when they find it in their stocking! On second thought, maybe not the best idea unless you want to spend New Year's sleeping on the couch. Remember, personal gifts are about love and appreciation, not tax deductions!

If you choose to use the holiday season as an opportunity to share goodwill with your business network, it's important to know that purchasing gifts for individuals and businesses within this network can be considered a deductible expense. This allows you to express appreciation while also benefiting from potential tax deductions.

I deeply value aligning my business principles with a spirit of generosity, and the end of the year is a wonderful opportunity to share my business successes with those around me. For example, with SimpliMD, I was able to make a significant donation to our Donor-Advised Fund (DAF) before the year's close. This pass-through business model allows me to take advantage of charitable donations now and use my DAF for future distributions. It's truly fulfilling to contribute in such meaningful ways.

A Gift for Your Professional Growth

As we reflect on the meaning of generosity during the holiday season, it’s also a perfect time to think about investing in yourself. At SimpliMD, we believe in empowering physicians to thrive both personally and professionally. That’s why we’re offering a personalized micro-business consult for only $99. This consult includes a one-year SimpliMD membership—a $2,500 value—packed with tools, resources, and support to help you succeed.

Take the first step toward a more fulfilling and independent career. Give yourself the gift of professional growth and freedom this holiday season.

Sign up for your personalized consult today.