An Entrepreneur’s Guide For Knowing When To Take A Vacation


Most of us suffer from something called overconfidence bias, meaning that there's a significant gap between our belief in what we can accomplish, and the reality. I would imagine that the gap gets even wider for most entrepreneurs. I don't have any research to back this up, other than proof that if you can quit your job and step into an unknown world, create something new, and expect people to actually buy it, well, you must be pretty damned confident.

Most of us suffer from something called overconfidence bias, meaning that there's a significant gap between our belief in what we can accomplish, and the reality. I would imagine that the gap gets even wider for most entrepreneurs. I don't have any research to back this up, other than proof that if you can quit your job and step into an unknown world, create something new, and expect people to actually buy it, well, you must be pretty damned confident.

Where overconfidence bias tricks us up is when the rubber meets the road. It's the end of the day, your list of to do's is still long, and you make the decision to forego personal time and just keep grinding.

This seems like a great idea at the time, but it's only short-term thinking. I propose that entrepreneurs take a long-term thinking approach to their productivity, much like we should be doing with our business strategy, finances, and everything else. In fact, when it comes to your personal health, it feels like that should be priority number one, simply by reasoning that if you fall ill or drop dead, the rest of the planning really doesn't matter. With this in mind, here are 5 ways to know that it's time for you to take a break. Whether it's a formal vacation, or simply a meditative walk, the goal is to clear your mind so that you can perform to your best, over the long-term.

1: You're exhausted, but forcing yourself to keep going.

Jeff Bezos recently said that sleeping 8 hours per night is key to him, and his shareholders, in making good decisions. A host of other entrepreneurs, including Arianna Huffington, are declaring lack of sleep, and burnout, a multi-billion dollar crisis. Regardless of how much you want to keep going, when you're feeling lethargic you have to stop. You decision-making skills, logic and reasoning are not in the right place for you to work. And the risk of burning out is simply too high. Make good micro-decisions, for long-term greater productivity. Follow the example of the greatest entrepreneurs today and be sure to get 8 hours per night, catch up on any hours you lose, and take mental, and physical, breaks throughout the year. Your overconfidence biased brain may not believe it's necessary, but all research points the to the opposite.

2: You're stressed.

I do a lot of work in corporate culture design with emphasis on workforce wellness. Researchers have found that the costs of high-stress environments will kill a business. It's only recently that many businesses are willing to break free of the high-stress leadership styles and adapt to more long-term thinking. This applies to entrepreneurs as well. Imposing high levels of stress on yourself and your work will speed up short-term productivity, but at a great cost. Organizations with high-stress show 40% more absenteeism, make 70% more accidents, and have 50% higher healthcare costs[1]. Why are the numbers so high? Depleting your cortisol levels is bad for your mental state and bad for business. It leads to health issues, less precision, and burnout.

Take a daily assessment of your stress levels. If you're feeling out of balance, the answer isn't to work harder, it's to stop work altogether. Think about how many times you've made yourself sick from stress. All of us high-performers do it naturally, so the need is urgent to stop ourselves. A week out of work because you're not well is a greater cost than taking an hour of mental vacation to do something you enjoy.

If some people didn't tell you, you'd never know they'd been on vacation." -Kin Hubbard, American Cartoonist

3: You feel weak.

Your mind is still whirring away at your entrepreneurial venture, but your limbs just don't seem to keep up. In the fitness world we call this “dead arms" or “dead legs". It's the byproduct of over-fatigue. This can happen to you from typing on a laptop too much, just as easily as it can from lifting weights. Dead arms or dead legs means that your body is fatigued. To get your limbs back to operating at their best, its time to increase blood flow. Get a massage, or even better, get a workout in. I know it seems counter-intuitive, but when you're fatigued, a workout will increase your blood flow, which reduces the fatigued feeling you're getting. Force yourself outdoors for a run, on the treadmill, or take a fitness class. If you aren't the fitness type, I am a huge proponent of cryotherapy for body recovery. Find a cryo spa near you and give it a try. Most offer a discounted first time rate. It only takes stripping off your clothes and three minutes to get your body feeling brand new again.

4: You Feel Depressed

Depression is incredibly common among entrepreneurs for a laundry list of reasons. If you're feeling down, a great way to overcome your blues is to get out and attend a networking event or social gathering. When you're depressed this is exactly the opposite thing of what you want to do, and absolutely what you need to do. Connection is the opposite of depression. Neural networks are shown to improve in mid to moderately depressed people who attend social events. Get out and re-wire yourself, ASAP.

An often-overlooked aspect of entrepreneurial management is emotional self-management. We have to focus on our mental and emotional game as a priority if we're meant to perform at our very best. As an entrepreneur, you don't have a boss to tell you to keep going, or to take a break. Take on the role of your own boss. Keep your body and mind feeling great. Your business is counting on it.

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How Postpartum Mesh Underwear Started My Entrepreneurial Journey

"Steal the mesh underwear you get from the hospital," a friend said upon learning I was pregnant with my first daughter.

It was the single best piece of advice I received before giving birth in December 2013. My best friend delivered her daughter eight months previously, and she was the first to pass along this shared code among new moms: you'll need mesh underwear for your at-home postpartum recovery, and you can't find them anywhere for purchase. End result: steal them. And tell your friends.

My delivery and subsequent recovery were not easy. To my unexpected surprise, after almost 24 hours of labor, I had an emergency C-section. Thankfully, my daughter was healthy; however, my recovery was quite a journey. The shock to my system caused my bloated and swollen body to need weeks of recovery time. Luckily, I had trusted my friend and followed her instructions: I had stolen some mesh underwear from the hospital to bring home with me.

Unfortunately, I needed those disposable underwear for much longer than I anticipated and quickly ran out. As I still wasn't quite mobile, my mother went to the store to find more underwear for me. Unfortunately, she couldn't find them anywhere and ended up buying me oversized granny panties. Sure, they were big enough, but I had to cut the waistband for comfort.

I eventually recovered from my C-section, survived those first few sleepless months, and returned to work. At the time, I was working for a Fortune 100 company and happily contributing to the corporate world. But becoming a new mom brought with it an internal struggle and search for something “more" out of my life--a desire to have a bigger impact. A flashback to my friend's golden piece of advice got me thinking: Why aren't mesh underwear readily available for women in recovery? What if I could make the magical mesh underwear available to new moms everywhere? Did I know much about designing, selling, or marketing clothing? Not really. But I also didn't know much about motherhood when I started that journey, either, and that seemed to be working out well. And so, Brief Transitions was born.

My quest began. With my manufacturing and engineering background I naively thought, It's one product. How hard could it be? While it may not have been “hard," it definitely took a lot of work. I slowly started to do some research on the possibilities. What would it take to start a company and bring these underwear to market? How are they made and what type of manufacturer do I need? With each step forward I learned a little more--I spoke with suppliers, researched materials, and experimented with packaging. I started to really believe that I was meant to bring these underwear to other moms in need.

Then I realized that I needed to learn more about the online business and ecommerce world as well. Google was my new best friend. On my one hour commute (each way), I listened to a lot of podcasts to learn about topics I wasn't familiar with--how to setup a website, social media platforms, email marketing, etc. I worked in the evenings and inbetween business trips to plan what I called Execution Phase. In 2016, I had a website with a Shopify cart up and running. I also delivered my second daughter via C-section (and handily also supplied myself with all the mesh underwear I needed).

They say, “If you build it, they will come." But I've learned that the saying should really go more like this: “If you build it, and tell everyone about it, they might come." I had a 3-month-old, an almost 3 year old and my business was up and running. I had an occasional sale; however, my processes were extremely manual and having a day job while trying to ship product out proved to be challenging. I was manually processing and filling orders and then going to the post office on Saturday mornings to ship to customers. I eventually decided to go where the moms shop...hello, Amazon Prime! I started to research what I needed to do to list products with Amazon and the benefits of Amazon fulfillment (hint: they take care of it for you).

Fast forward to 2018...

While I started to build this side business and saw a potential for it to grow way beyond my expectations, my corporate job became more demanding with respect to travel and time away from home. I was on the road 70% of the time during first quarter 2018. My normally “go with the flow" 4-year-old started to cry every time I left for a trip and asked why I wasn't home for bedtime. That was a low point for me and even though bedtime with young kids has its own challenges, I realized I didn't want to miss out on this time in their lives. My desire for more scheduling flexibility and less corporate travel time pushed me to work the nights and weekends needed to build and scale my side hustle to a full-time business. If anyone tries to tell you it's “easy" to build “passive" income, don't believe them. Starting and building a business takes a lot of grit, hustle and hard work. After months of agonizing, changing my mind, and wondering if I should really leave my job (and a steady paycheck!), I ultimately left my corporate job in April 2018 to pursue Brief Transitions full-time.

In building Brief Transitions, I reached out to like-minded women to see if they were experiencing similar challenges to my own--balancing creating and building a business while raising children--and I realized that many women are on the quest for flexible, meaningful work. I realized that we can advance the movement of female entrepreneurs by leveraging community to inspire, empower, and connect these trailblazers. For that reason, I recently launched a new project, The Transitions Collective, a platform for connecting community-driven women entrepreneurs.

As is the case with many entrepreneurs, I find myself working on multiple projects at a time. I am now working on a members-only community for The Transitions Collective that will provide access to experts and resources for women who want to leave corporate and work in their business full-time. Connecting and supporting women in this movement makes us a force in the future of work. At the same time, I had my most profitable sales quarter to date and best of all, I am able to drop my daughter off at school in the morning.

Mesh underwear started me on a journey much bigger than I ever imagined. They sparked an idea, ignited a passion, and drove me to find fulfillment in a different type of work. That stolen underwear was just the beginning.