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Now What? 3 Questions to Intentional Generosity

Jessica Winter

Jessica Winter

August 7, 2020

“So now what?” My husband and I started asking this question about our generosity this year, and it has led us down many new paths. We love the opportunities we have to live generously, but that itch of something more has been following us around recently.

I started asking people about their experiences, and I heard so many interesting stories. One woman would simply divide up the requests and send out her checks at the end of the month. Another person told me about how they were committing 20% of their business profits for the rest of the year. A friend encouraged me to think about joining forces with some others all contributing to a particular cause.

The beauty but also the challenge of generosity is there is no one-size-fits-all approach. It genuinely is the unique ways we reflect God’s heart.

However, with this mindset to be proactive as stewards of how God has blessed us, it still has kept driving home that “Now what?” question in my mind. My husband and I want to take advantage of all we have been given and not settle for a good but generic plan. We firmly believe real generosity is an active, ever-growing process. That does not always mean committing more dollars. Sometimes, it is the heart change that has to occur in us.

As we have begun this journey, I wanted to share a few questions that are helping us go a layer deeper into intentionality with our generosity.

Does this opportunity align with the values and impact we want to create?

When we first started giving, we had the typical list of good places to give, and while they all are great causes, we wanted to refine our focus. This question allowed us to begin a more strategic list to find the groups that more closely aligned with the impact we want to see occurring, and we plan to continue these re-evaluation moments.

Where do we need to invest and store up?

After watching so many struggles in the wake of COVID-19, it left a tremendous burden on our hearts to wish we could do more. Part of being a steward is not just giving money away but being wise in preparation as well. We want to be able to respond as God moves, so putting effort into ways to invest and store up allows us to be ready.

How can we live more yielded to God’s call?

Before you gloss over this as a cliché, let me challenge you to dwell on this idea, because it actually has been one of the most essential pieces to the change in our generosity. Before even worrying over money, when we started to turn over pieces of our lives to God’s hand, that is where the opportunity for real generosity showed up. From cutting down time on social media to more phone calls with friends in need, humbly giving back made space for God to show up and open doors we never would have seen.

My prayer is that you will never be satisfied in your generosity journey. I think that is the joy of walking with the Lord. There is always something new in His abundance and goodness, and I love that the adventure of generosity sends us chasing after Him daily down roads we never even managed we would be on. Oh the delight to be a vessel in His work!

Whether you have been giving for 5 weeks or 5 decades, we all would do well to go back to these key questions so we keep refining, growing, and engaging in God’s glorious work. Maybe you lost your sense of wonder. Maybe you are thriving and ready to go even deeper. Maybe you are searching for passion. Wherever you are, come back to these questions to shape your next stage. Alignment, investment, and obedience are the keys here.

Tell me your amazing stories of generosity! I love the inspiration, and I would love to share with others. We are better together as we learn from each other’s journeys. Submit your story here.


About Jessica Winter

Jessica Winter

Jessica is the former Chief Brand Officer of The Signatry.

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