Harnessing Creativity and Leadership: Andie Asacker’s Entrepreneurial Journey

Andie Asacker was laid off in December 2020, and by the day she registered her LLC she already had clients. On this episode of Leadership With a Twist, Barbara Schindler talks with Andie, digital strategist and founder of Whirlybird, a one-woman marketing agency in the heart of Vermont, about what happens when a business grows faster than the plan behind it.

Andie spent nearly 15 years in sales and marketing managing six-figure advertising portfolios before going out on her own. She is also a musician, dancer, choreographer, fire spinner, potter, quilter, watercolor painter and illustrator, which says a lot about how she approaches work. She and Barbara get candid about the blurry line between work Andie and creative Andie once no employer sets the clock, and why she now chooses no more than three markers each morning that tell her the day is complete. She walks through the practical mistakes of her early years too: an unemployment case she won because she took notes on a single phone call, quarterly taxes she managed to both overpay and underpay, and a fee she paid for five years that she never owed. The deeper lesson took longer to see. If you don't steer your business, even as a solopreneur, it steers you by whatever lands in the inbox.

From there the conversation moves into platform instability in digital marketing, why Andie tells clients she learns alongside them every time Meta changes, and something she calls shiny software syndrome. Barbara lays out the stages leaders move through with change, from feeling it happen to them toward co-creation and flow, and both land on a new paradigm of leadership where everyone leads themselves first.

Key Takeaways

• Choose one to three markers at the start of each day that define complete, so an endless to-do list doesn't decide when you stop.
• Sitting at your desk all day is not the same as being productive. When you're circling the drain, a walk often moves the work further than another hour in the chair.
• If you don't hold the steering wheel in your business, incoming requests will, and you can drift far from what you intended at the start of the quarter.
• Foundational skills like communicating clearly, asking good questions and knowing how you'll measure success outlast any platform or algorithm.
• Getting your lessons faster keeps deliberate pacing from sliding into perfectionism and rumination.
• The question that makes you nervous to ask is usually the one someone else in the room has been holding too.

Action Steps

1. Before you open your inbox tomorrow, write down the markers that will tell you the day is done.
2. Build stop points into big projects so 5:00 has a natural place to land instead of a scramble.
3. Get help with taxes and business setup early, before a letter shows up a year later.
4. Before switching to new software, name the specific problem the current tool is failing to solve.
5. Put one idea in front of other people this week and pay attention to what comes back.

Questions to Reflect On

• Where is your business steering you right now, and is that where you want to go?
• Which foundational skill have you skipped in favor of the newest tool or tactic?
• When did you last ask the question in the room that nobody else was asking?

Connect with Andie:
https://www.whirlybirdonline.com
@whirlybirdonline on Instagram

Let's Talk
If this conversation stirred up questions about how you're leading yourself and your business, bring them to a complimentary call with Barbara. We'll look at where your work is steering you and what it takes to get your hands back on the wheel: https://www.empoweringleadershipteams.com/discovery

More about Andie:

Andie Asacker is a digital strategist, creative powerhouse, and the founder of Whirlybird—a one-woman marketing agency based in the heart of Vermont.

She's spent nearly 15 years in sales and marketing—managing six-figure advertising portfolios, representing Fortune 500 brands, and playing key roles in small businesses and startups. Whether creating stunning visuals or meticulous spreadsheets, Andie is happiest at the intersection between inspiration and execution.

She brings a fresh perspective and keen attention to detail to her work, designing logos, websites, theater sets, trade show booths, and SOPs.

She is also a musician, dancer, choreographer, fire spinner, potter, quilter, watercolor painter, and illustrator. Andie loves the ins-and-outs of bringing ideas to life! Creativity isn't just what she does, it's how she's wired.