Why Do I Feel Guilty Asking for Help? | Ashley Chang Dawson

From Don't Cut Your Own Bangs · 54:04

Show by Danielle Ireland

Do you ever feel like you should be able to handle everything yourself, even when you're completely overwhelmed? Sometimes the hardest part of asking for help isn't finding someone who can help. It's believing you're allowed to need it in the first place. In this episode of Don't Cut Your Own Bangs, I'm joined by Ashley Chang Dawson, co-founder and CEO of Sundays, an executive assistant service helping working parents reclaim time, energy, and possibility. And this conversation is especially personal because I've recently started working with an executive assistant through Sundays myself. As a therapist, mother, wife, and business owner, I've spent a lot of time thinking about support. And lately, I've been learning that being capable of doing something doesn't necessarily mean I need to be the one doing it. Ashley and I explore the invisible mental load, the motherhood penalty, why our identities can become so tangled up in productivity, and what happens when we finally give ourselves permission to receive support. We also talk about something that doesn't get nearly enough attention: what happens when you finally have time back, but you're so accustomed to being busy that you don't know how to let yourself enjoy it? Because sometimes the question isn't whether you can do it all. It's what doing it all yourself might be keeping you from. In This Episode, We Explore Why asking for help can feel so uncomfortable. How we create arbitrary milestones for when we've finally done enough to deserve support. The difference between being productive and being supported. Why constantly responding, managing, and anticipating everyone's needs can become part of our identity. How to reclaim your time and energy. Ashley shares a practical time-and-energy audit for identifying the responsibilities that matter but consistently drain you. We also discuss the pressure working mothers experience to balance ambition and family, how support can look different in different seasons of life, and why having more time doesn't automatically mean you need to do more. And, of course, Ashley shares her Don't Cut Your Own Bangs moment involving wedding planning, a questionable rental car company, and a lesson about the true cost of cutting corners. A Moment Worth Remembering Ashley describes how uncomfortable it felt to mute a Slack channel she'd become accustomed to checking every morning—even after she'd handed responsibility over to a capable team. It wasn't just about delegating a task. It was about learning that she didn't need to be on high alert all the time. A Question to Take With You What is doing everything yourself keeping you from? Not just in terms of time. But energy, creativity, connection, rest, and the parts of your life you might want more room for. Something You Can Try This Week Look at your to-do list and ask yourself two questions about each responsibility: How important is this? Does it give me energy or drain my energy? Notice the things that are important but consistently draining. Maybe you can ask for help with one of them. Maybe you can simplify it. Or maybe you can group a few of those tasks into one designated hour instead of carrying them around in your head all week. The goal isn't necessarily to get more done. It's to become more intentional about what you're giving your time and energy to. One More Thought Knowing how to survive is different from knowing how you want to live. So here's one more question I'd love for you to consider: Wouldn't it be nice if... Finish that sentence without immediately worrying about the logistics. Maybe the clearer you become about the life you want, the easier it becomes to recognize the support that could help you create it. Meet Ashley Chang Dawson Ashley is the co-founder and CEO of Sundays, a company providing executive assistant support to working parents. After working in the technology industry, Ashley began noticing how many talented women were stepping back from career opportunities as the demands of family life increased. Through Sundays, she's working to address the motherhood penalty by connecting parents with executive assistants who can help manage responsibilities across work and home. Sundays offers a flexible, personalized approach to support, with a team of assistants who are themselves mothers and caregivers. Learn more about Sundays: [Guest website — link to be added] Connect with Ashley and Sundays: [Guest social links — to be added] Bring These Conversations to Your Organization If you're planning a conference, leadership gathering, women's initiative, or team event, I'd love to bring conversations like this into your room. My speaking work explores burnout, emotional wellbeing, communication, boundaries, and what it means to care deeply without carrying everything. Learn more about booking me for your next event at: https://danielleireland.com Stay Connected Danielle Ireland — Therapist, Speaker & Podcast Host Website: https://danielleireland.com…

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