Keep Asking: Lessons in Not Holding Back

On this week’s episode of the Fundraising HayDay Podcast (Season 4, Episode 14), Kimberly and I had the great fortune to chat with Sarah Stewart Holland and Beth Silvers of the popular podcast, Pantsuit Politics. We didn’t stick with a theme for the episode, but rather asked all the questions we wanted to, from earmarks and use of data to having difficult conversations and being okay with changing your mind. You can take a listen here: Earmarks, Quality Data, and Difficult Conversations (


As I was thinking over what aspect of that interview I wanted to focus on in this blog post, it hit me that the interview itself was the thing. If you haven’t heard of Pantsuit Politics before you might not understand, but it was a big deal to Kimberly and me that Beth and Sarah took the time to join our show. They have a HUGELY successful, twice-weekly podcast, with a large and very engaged community behind them. It would have been extremely easy to not even ask, worried that they would say no or simply ignore our request, but several seasons ago Kimberly and I decided to dream big. Big name we’d like to interview? Ask. Read a book and love the author. Ask them to join the show. Hear about an expert in our field who would bring a wealth of information to our listening audience. JUST ASK.


We have been ignored. We have heard “no.” But we won’t stop asking. Because some people say yes. And that is the lesson I want to share with you today. We can worry about what someone else will or won’t say, or we can seek the things that will bring us happiness and success. This is how I try to live my personal and professional life, and it has led to experiences I would have otherwise missed. For instance, last year an individual I knew from church posted on Facebook that she was looking for someone with social media experience to work a few hours a month for her digital marketing firm. Until then, my experience went no further than rambling on Facebook, but I knew I wanted to learn more to better market the podcast online. I called her up, told her I would love to give the job a try and selfishly learn everything I could from her team. A year later, I’m still learning from her, but would like to think I have upped my game thanks to the shot she gave me.


In that vein, let me encourage you to try something new this year. Have you always wanted to speak at a conference? Apply. And if you don’t want to make that leap alone, find a friend and tag team. Having worked from home during the pandemic, you may have no desire to go back to a cubicle at the office. Open up dialogue with your boss and explain how much more productive you are when telecommuting. Even if they want you in the office two days a week, that’s a better compromise than every Monday through Friday. Want to serve on a leadership role in your professional organization? Find a volunteer role on a committee and work your way up to the top position.


Twenty years ago, right after college, I was too nervous to have some of these conversations with coworkers, colleagues, or bosses. I was a people pleaser, and often eager to put the needs of others first. I’m still a people pleaser by nature, but I have learned that pleasing others does not mean having to forgo the things that will enrich my own life. So, take stock of what you want for your professional life, and ask the questions, take the opportunity, make the leap. Just don’t hold back.


DH Leonard Consulting & Grant Writing Services, LLC is so excited to be season 4 sponsors for Fundraising HayDay, a podcast about grants and such. Catch up on seasons 1 – 3 and stay up to date on the new season here.

Don’t let grants stress you out, check out the helpful grant writing services our team has to offer here.


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