The Trusty Oak Blog

How & Why Entrepreneurs Should Take Vacations

feet at beach

Several months ago, I was invited to attend a friend’s wedding in St. Lucia. I hesitated to book the trip because I already had another trip planned to NYC just one month before the Caribbean trip, and I was worried about taking more time out of the office. (Even though these trips would be the first trips I took since starting the company almost a year ago.) With the persuasive comments from my friends and husband, I booked the non-refundable trip to an island in the sun.

As the trip date grew closer, I started feeling anxious about going and began to consider staying home – even though I would lose my money. I felt anxious about leaving the office and had some time-sensitive “to-dos” in my personal life as well. I had just hired a new Trusty Oak virtual assistant that I was training to serve one of our most long term clients.  I hadn’t hit my goal in sales for the month – in fact, we were far from it. And on top of everything at the office, I was selling my house. It started feeling like terrible timing.

How could I leave for five days in the middle of this madness?

And an even better question: Why would I leave?

Well, I went on the trip and it was the best thing I could have done for myself and for my business – despite it being what seemed to be the worst time to check out. This post answers these two questions that entrepreneurs like me are likely asking themselves when presented with an opportunity to take some time off.

How Entrepreneurs Take Vacations


The key to being able to leave my business for a few days can be summed up in one word: TRUST.

If I did not have amazing people on the Trusty Oak team, I would not have been able to leave for five days. I like to say that I have been blessed with an incredible team. That’s true, but it may be more accurate to say that I have been blessed with the ability to surround myself with incredible people. When selecting new virtual assistants for Trusty Oak, I am not only interviewing candidates for their competence, but I’m also asking questions regarding their character. One of my favorite books, The Speed of Trust, by Stephen M. R. Covey introduced me to the idea that trust is equal parts character and competence. It’s a simple concept. We trust people that we believe are experts in their field or industry and we trust people who behave with integrity, honor, respect, empathy, and a number of other positive attributes. Both parts of trust are important.

I knew that when I left the country for a few days, the business would be in good hands. Our clients would be in good hands. And I was right.

Nothing fell apart while I was gone.

The name of our business was born from this idea regarding trust. Trusty Oak virtual assistants are team members I trust and so can our clients. If you are a business owner who hasn’t taken a vacation in a couple of years because you are afraid the business will implode in your absence, give us a call. We can help with that!

But what about the other question? Why would I leave when I was behind on sales and juggling several other challenges?

Why Entrepreneurs Should Take Vacations

Honestly, I was feeling super stressed and stuck. My energy level was waning, and I was struggling to do the things that I knew would “move the needle” for my business.

If you work from home, you likely face some of the same temptations I do. I’m easily distracted by the pile of dishes in the sink or the weeds cropping up in the flower beds. I don’t watch much TV, but I know this can be a common distraction for others when they are feeling unmotivated. And if I’m honest, (I’ll be honest) I have to admit that I find myself clearing social media notifications off my phone constantly in an attempt to relieve stress. My mind knows this doesn’t help anything, but I seem to do it without thinking sometimes. And of course, this is killing my productivity.

I needed to be setting meetings, but I didn’t want to leave my house. I would work all day and wonder what I had to show at the end of the day. I was feeling further behind every day, and overwhelmed by the growing list of things I hadn’t done yet.

The cure? I delegated some of the list a few weeks before I left, and decided it was ok to leave some things undone while I was gone. These things would be there for me when I got back.

The vacation was short, but it was just enough time for me to take a few naps oceanside, enjoy great food and drinks and share some laughs with friends. Like usual, I wasn’t really excited about coming back to reality, but when I did make the reentry, I felt like a new person. I jumped back into my routine, filled my calendar and got to work.

And the best part?

I was exponentially more productive and started seeing immediate results.

The to-do list started getting shorter. The sales started coming in. The joy was back.

What about you? Have you ever taken a vacation in the middle of crazy times at work? I’d love to hear about your experience in the comments below!


How it Works

Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.