EP 001: Let Go of Control to Gain Freedom in Your Business

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Ann Handley—author, marketer, sought-after public speaker, and founder of MarketingProfs—still remembers the first time she emailed Don’t Panic Management’s Jess Tyson.

It was Sunday morning and she was weeding through her crowded inbox on a weekend (again). Dedicating those precious weekend hours to catch-up work had become a regular routine, and Ann finally hit her breaking point. She sent Jess an email with a three-word subject line: “I need you.”

And the rest is history! Ann and Jess have been working together for nearly a decade. Of course, they are a well-oiled machine at this point, but things didn’t start out that way. Ann is a self-described control freak, so it was a big leap of faith for her to let a virtual assistant into her life and her business.

Ann admits she was wary of working with a VA at first. Handing over all her passwords, credit card information, and license details made her keenly aware that, if a VA wanted to, they could absolutely take her down.

Aside from this practical fear, Ann also had bigger emotional fears about what hiring help meant for her brand. If you know anything about Ann, you know that her personal brand is all about accessibility, and she prides herself on that. If she wasn’t the one doing everything and personally answering every email, would that fundamentally change her business?

Ann says that after getting over those initial hurdles, she’s learned there’s so much to gain in letting go of some of that control. While the business is still very much Ann’s, much of the operational framework has been laid by Jess over the years. Ann credits Jess with setting up a system that’s allowed her to evolve and elevate the business in ways she never thought possible.

“The reality is that by letting go, I’ve actually gained more control,” says Ann.

Aside from the logistical support Jess brings to the table by creating processes for doing work behind the scenes, Ann says that what’s been most surprising about the VA-entrepreneur relationship is that Jess also brings creative support and acts as a critical sounding board.

Ann notes that it was Jess who first encouraged her to raise her speaking rates, unprompted. A strong VA, she says, can provide you a bird’s eye view of your business, minus the emotional attachment you feel. Ann also knows she can turn to Jess to help execute her wackiest creative visions. (Tune in to the episode to hear a story about a particularly memorable speaking gig in Vegas.)

Now, Ann can’t imagine entrepreneurial life without the help of a skilled VA. So what’s the one piece of advice she’d provide to others who are thinking about finding an assistant?

”Don’t approach it like an assistant. Approach it like a partnership,” she says.

A great VA is so much more than a person mindlessly pressing the buttons behind the scenes. They’re a builder of frameworks and processes, a trusted confidante, and an enthusiastic accomplice in helping you realize your wildest, most creative dreams.

Key Takeaways

  • A great VA is like a spouse (or perhaps a skilled therapist). They provide support that goes well beyond logistics and can act as a supportive but non-partisan sounding board for business decisions.
  • The “virtual” piece of a virtual assistant opens entrepreneurs up to finding the right talent beyond the bounds of their hometown.
  • Even if you run a seasonal business, it’s important to have support year-round. In fact, Ann finds that when she’s in the “off-season” for her speaking work, having a VA allows her to take on special projects that lay the groundwork for long-term growth.

Top Quotes

“What people see is me—they’re still getting me, they’re still seeing all of that wrapping—but the foundational stuff is all you.” – @annhandley on the power of working with a virtual assistant. Share on X “The real benefit for me is feeling like I have a partner who can talk through options with me. Having that resource is enormously helpful for someone like me who is otherwise running the business on their own.” – @annhandley on how… Share on X “It’s not just about finding a person to do things, but finding that person who is able to provide the things to create a stronger whole.” – @annhandley on finding the right virtual assistant. Share on X

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