Embracing the Uncontrollable: Lessons in Letting Go with Valerie Trapunsky

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Show Notes:

Being a business owner requires a wide range of skills, but effective delegation is definitely one of the most critical ones. But how do you let go of control and learn to effectively delegate tasks? Our guest will tell you all about it.

Meet Valerie Trapunsky. Valerie is the Founder and CEO of ChatterBoss, a company helping busy entrepreneurs find hand-picked executive assistants. After spending more than seven years working as a top-level personal assistant and Chief of Staff for A-List celebrities, CEOs, and high-net-worth individuals, Valerie discovered that she could bring the same level of excellent service to individuals, entrepreneurs, and small business owners. And that’s how the idea for ChatterBoss was born. Valerie has been the CEO of this startup for six years and has built a network of over 175 high-performing executive assistants, now supporting entrepreneurs across the country. Her vision is to give every entrepreneur access to their dream team.

Valerie is an inspiring thought leader in the world of remote team building, entrepreneurship, and productivity. She’s full of wisdom about building trust, effective communication, and successful delegation.

In this episode of the Think Business With Tyler podcast, we talk about the importance of effective delegation for entrepreneurs, how to build trust with your assistant, the benefits of cleaning off your mental chaos, and tips for letting go of control in life.

If you want to free up your time and learn to delegate, make sure you tune into this episode to hear what Valerie has to say.


💡 Name: Valerie Trapunsky

💡 What she does: She’s the Founder and CEO of ChatterBoss.

💡 Noteworthy: Valerie has been the CEO of this startup for six years and has built a network of over 175 high-performing executive assistants, now supporting entrepreneurs across the country.

💡 Key Quote: “The way that we onboard people virtually is different than the way that we onboard people in person. When we are in person, someone can sit next to you all day and literally shadow you. You cannot do that in the same way in a virtual space.”

💡 Where to find Valerie: LinkedIn

Key Insights

Delegation is a vital skill for entrepreneurs. Time is of the essence, especially for busy business owners. That’s why delegating tasks is key to success in business. If you want to free up your time and focus on your area of expertise, you need to learn to delegate your tasks and let go of control.

Valerie explains, “When you are delegating, where are your specific stoppers when delegating? And we all have specific stoppers when delegating, but there is this other world of it, which is, what is my character, what’s my personality? And then there are certain stoppers that I’m going to have individually that are kind of ingrained, baked into who I am, and some of those are harder to overcome. For example, individuals that are real perfectionists or struggle with control, which a lot of entrepreneurs end up being in that category, will then have their own unique hurdles when it comes to delegating because so much of delegating is about relinquishing control and setting different types of expectations.”

Trust is of utmost importance, especially in a virtual environment. One of the most critical factors in every business relationship is trust. And when working with a personal assistant, trust is non-negotiable. So, how do you build trust in a virtual environment? Luckily for all entrepreneurs, Valerie has a few tricks up her sleeve.

She says, “In the virtual world, what we have over the last six years found was that there’s a formula for developing trust. And it’s pretty exciting to discover because then you can replicate it, and you can recommend it to individuals stepping into these relationships. But we’ve found is that you, in order to start and gain trust, you have to delegate one or two very clear and measurable tasks at the start.”

Clean off your mental desk. Entrepreneurs have a lot on their plates. From handling client communication to sending out invoices, there are so many things to worry about when you’re a business owner. But how do you find the time to come up with new ideas for your business, then?

Valerie says that hiring assistants is one of the best ways to clear off your mental clutter. She explains, “The idea of white space when we’re talking about partnering with administrative professionals is to be able to clean off of your mental desk, these things that you don’t need to be focusing on. So then those, maybe three large items are there, and you can give your full attention. It’s like your battery is not being drained by the apps in the background, you’ve turned them all off, and you’re only concentrating on what you have in front of you.”

You can’t control everything. Learning to let go of control as a business owner is a difficult challenge. But you need to accept the fact that you can’t control everything in life. Instead, focus on the things you can control and just enjoy the ride.

Valerie says, “It goes up, it goes down, and then it goes all the way up, and we kind of don’t know where it all ends, ultimately is going to end. But what we have to do is enjoy the ride. And the ride is much more enjoyable when we can give in to the fact that there’s things that we can’t control. Focus on what we can control and just keep going forward.”

Top Quotes

“I’m the kind of person that really lives in the moment, and so I’m very inspired about the events that happened to me. So the truth is, I never planned to be a personal assistant. I never planned to be a chief of staff. That was certainly never in my idea of a career trajectory, but it’s something that happened. And then it was a very natural evolution to start Chatter Boss from there because I was very passionate about business and I have that kind of entrepreneurial drive, and so there, there was the combination of learning a lot about it, a very niche industry, and then having that light bulb turn on.”

“The worst is where it’s like, everything is boiling. You don’t know where it is. And we have a number of different worksheets and, like I said, a lot of different matrices to just identify where is the problem. And the worst is when someone says like, oh, it’s just you’re a bad person. It’s never that. It’s always there’s a mismatch. And usually, I find that people have the best intentions, and if you do have to separate, you can separate amicably.”

“It’s your responsibility as business owners to facilitate the creation of the core values.”

“My personal goal is to be able to contribute to the field of psychology in the space of outsourcing and delegation by adding meaningful literature that’s published by us through observation of clients and assistants.”

“Different stages of our lives in our business bring off these different things. My theme right now in both business and in my personal life is that life will and business will test you. The market will test you. And what I’ve found is that things that look bad end up being good, and things that look bad sometimes might be good. The opposite.”



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