Thanksgiving Reflections: Smart Strategies for Living Generously
As Thanksgiving approaches, it’s natural to pause and count our blessings.
But what if gratitude didn’t stop at feeling thankful—and instead became a way of living that enriches not just your life, but the lives of everyone around you?
Many of us feel especially generous during the holidays, but feeling generous and living generously aren’t the same thing. Feelings can fade; intentional action builds lasting joy and fulfillment.
This guide will help you turn good intentions into consistent, meaningful generosity—through practical strategies that align with your family’s values and your long-term financial goals.
What “living generously” really means
Generosity isn’t just writing a check in December. It’s a way of life that aligns your values, resources, and impact.
Values: What do you care about most? (Faith, family, education, local community, global missions, foster care, food insecurity, etc.)
Resources: What do you have to give? (Time, money, skills, wisdom, relationships, influence.)
Impact: How do you know it’s working and that your efforts are well spent? (Clear goals, consistent habits, and occasional course-corrections.)
StillWater’s approach: We support clients with financial planning by using the acronym of TIGERS- Taxes, Investments, Generosity, Estate, Risk, Savings/Spending). We think it is quite fitting that generosity falls in the middle of that acronym because we believe a person’s convictions around generosity drive all the other aspects of financial planning and breathe life & purpose into the plan itself.
So, if you see tend to see things in life like I do, or I have at least piqued your interest, then we are on board with the potential value of pursuing a purposeful, generous life. But it is all just theory until we take action, so where do we start?
💡 Don’t have time to dive in right now? Download our Quick Start Checklist
Step #1 - Build a Purposeful Giving Plan
Block one hour with your spouse or a trusted loved one to go through our detailed guide:
Step #2 - Give Smarter with Tax-Wise Strategies
A) Donor-Advised Fund (DAF)
What it is: A charitable account you fund today and recommend grants from when you choose over time.
Why it helps: Potential immediate tax deduction when you contribute, with flexibility to give later; can donate appreciated stock and other investments to avoid paying taxes on capital gains.
Best for: Families who want to bunch deductions in a single year, give appreciated assets, or create a “family foundation feel” without the complexity.
💡 Name your kids as successor advisors to instill generosity as a part of your legacy.
B) Gifts of Appreciated Securities
What it is: Giving stocks/ETFs/funds you’ve held over a year that have gone up in value.
Why it helps: You may avoid capital gains tax on the appreciation and potentially claim a charitable deduction (subject to IRS rules and limits).
Best for: Investors with large unrealized gains who want to maximize impact per dollar.
💡 We help clients identify the right lots of investment shares to give and coordinate delivery directly to your desired charity or your DAF.
C) Qualified Charitable Distributions (QCDs) from IRAs
What it is: If you’re 70½ or older, you can give directly from your IRA to eligible charities.
Why it helps: Amounts given this way can count toward your annual required distribution (RMD) once applicable, and if done correctly will not be included in taxable income—which is often better than itemizing a deduction.
Best for: Retirees who give regularly. Have balances in pre-tax retirement accounts, and want to reduce taxable income strategically.
💡QCDs must be paid directly to the charity (not to you first).
D) “Bunching” Strategy
What it is: Combine two or more years of giving into one tax year (often done by contributing to a DAF – see A), then grant to charities of your choice over time.
Why it helps: In the “bunching” years you may itemize (and capture deductions); in off years you would still take the allowed standard deduction.
E) Non-Cash Gifts that Often Get Overlooked
Private business interests (with careful planning)
Restricted stock/RSUs (leverage StillWater to assess timing/feasibility)
Real estate (outright or via a charitable remainder trust)
Personal property (vehicles/equipment with clear fair market value)
💡 These require more effort and due diligence, but can be well worth it in lifetime tax savings when done correctly. Involve your financial advisor, tax professional, and strategic experts early.
Step #3 Practice Generosity Beyond Money
This Thanksgiving, we challenge you to have a Gratitude and Giving meeting with your family. But don’t let the word meeting deter you, this can really be a special time of connection with your loved ones.
Go around the table: What are we grateful for this year?
Pick a cause: Let each family member nominate a cause.
Decide together: Choose at least one cause to support and talk through plans.
Make it tangible: Write a card, draw a picture, donate time, deliver a meal, assemble hygiene kits.
Create a “Giving Jar”: Fund it with part of allowance or side-gig earnings.
Script for kids: “In our family, we’re grateful and we share. We choose to help people because that’s who we are. By doing this we make an investment in people around us and believe that healthy relationships are one of the most important things in life.”
Step #4 Set Guardrails to Protect Your Giving (& Your Budget)
Automate first; impulse later: Set your core giving to run automatically.
Give from abundance, not from pressure: If you start to feel manipulation, urgency, or guilt – pause and walk away if needed.
Know the charity: Quick check: mission fit, financial transparency, local impact, leadership accountability. Not every cause or organization is a good one.
Avoid donor fatigue: Choose fewer causes and go deeper.
Leave room for spontaneity: You cannot script out every giving opportunity. Consider having a family RAK (random acts of kindness) fund.
Step #5 Measure Impact in Human Terms
Not every good thing is easily measured. Try a simple annual reflection:
What stories encouraged us?
Where did we see real change?
What did our family learn about compassion?
How did our gifts and actions make us feel?
What would we like to try differently next year?
💡 If it isn’t joyful or purposeful, adjust the plan.
Final Thoughts
With something as important and sacred as giving to others, there are a few pitfalls to avoid:
Waiting for “leftovers”: Plan to give and save first, budget the rest.
Letting taxes drive the mission: Tax efficiency is a tool, not the reason for giving.
Doing it alone: Bring in your family, advisor, CPA, and (if needed) an attorney. A capable team is more formidable than even the most gifted individual.
Spreading too thin: Many small gifts can dilute purpose, intentionality, and impact.
Impactful giving and intentional generosity is a fundamental part of who we are at StillWater. We would love to help with:
Leading you to clarity around your values and designing your Giving Plan.
Mapping out an optimal strategy for executing your giving plan.
Coordinating DAF setup and in-kind gifts (stocks/funds).
Evaluating QCD eligibility, timing, and implementation.
Integrating generosity with your taxes, investments, and estate plan.
Take Action: Are you intrigued by the idea of aligning your generosity with your life goals? Here at StillWater Financial Advisors, we’ll help you have clarity, confidence, and make steps that we believe will ultimately lead to an improved quality of life.
(This content is educational and not tax or legal advice. Talk with your tax professional about your specific situation.)
