This Founder Is Helping Us Spark Real-Life Connections

Welcome to our series “Ask A Founder,” where we tap into the great minds of female entrepreneurs making their big idea a reality. For the past two years, thousands of women have experienced our Selfmade virtual business coaching program, led by Brit + Co founder Brit Morin and sponsored by Office Depot OfficeMax. Here, we ask Selfmade alum Caitlin Iseler, founder of Happyly, “your guide to daily micro-wins,” about her aha moment, her ways to unwind, and how to recognize when you’re on the right journey.

1. How would you describe your brand in five words? Joy, connection, active, time-saving, wellness.
2. What was your aha moment before starting Happyly? Life isn’t meant to be lived on a screen! I craved more connection with those who mattered most in my world – in any given moment, that could include myself, my family, or my colleagues. As a working mom of a baby, I spent far too much time researching how to spend our limited time together and observed the need for reliable active lifestyle tools to catch up with other life-enabling technologies.
3. What were you doing before you started Happyly? I was a Partner at a global consulting firm in the technology practice. I loved my work but when I had the idea for Happyly, it was time to take the next step on my journey. I feel so blessed to be living my purpose alongside an incredible team, all passionate about making a meaningful impact in the lives of our Happyly community.
4. What’s one thing you wish you knew as an entrepreneur? Pivoting is not a sign of failure. Pivoting is recognizing the next right step on your journey.
5. How do you get in the right headspace to start your day? I love sitting in a coffee shop or at my kitchen counter with an unsweetened iced tea and reviewing and responding to high-priority email and Slack communications. From there, I review my calendar again to ensure nothing has changed and set alarms for the start and end times of every meeting so that I can be fully present.
6. What’s your favorite form of self-care? Hot 60 yoga, it’s my favorite thing!
7. What is your favorite desk essential? A candle!
8. Fill in the blank: The idea of helping others connect with themselves, their families, and their colleagues in ways that make life better gives me all the feels.
9. How has Selfmade helped you grow your business? I love the programming and amazing mentors. The community is inspiring and it’s always powerful to connect with other like-minded people.
10. What is the most powerful thing you do in your day? Be present at home, at work, and with myself. Easier said than done, but I’ll never stop trying.
11. What is usually prioritized on your to-do list? Being a mom and wife is always first. Supporting my team is a close second and, on the work side, is my #1 priority. From there, I dive into investor and customer interactions. It’s on my list of improvements to schedule workouts so they move up on the priority list.
12. How do you balance the practical and the creative parts of your business? I am a creative person first and operational second so the latter requires a lot more focus for me. I have to be very purposeful about carving out time to do things like reviewing P&L and budgets when I’m alone and without distractions.
13. How have Office Depot OfficeMax services/products helped you accomplish more in your business? We were so grateful to win the Office Depot OfficeMax gift card and it helped us to buy some awesome office treats. It’s always incredible to observe large brands doing good and not losing sight of how small business impacts the bigger picture.
14. What does the word “selfmade” mean to you? You’re in charge of your destiny and that’s a beautiful thing.

Thanks Caitlin! Entrepreneurship is not a linear journey and that’s ok. Pivoting means you’re learning and growing and building a better business. Office Depot OfficeMax can help you stay organized & save time with a suite of business services to help you accomplish more – from signs, posters & banners to get your business noticed to marketing materials to help bring your brand vision to life.