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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#GetFunded: The Best Way to Kick Off Pride as an LGBTQIA+ Entrepreneur

We're here. We're queer. Now that it's pride month, it feels like every store and corporation is flooding us with their best rainbow merchandise, capitalizing on a $917 billion dollar consumer market.

The rainbow flags are out. The mannequins are sporting pride tees. And corporate newsletters are full of interviews showcasing all their queer employees ("Look, we have a gay person here! We GET you!").

To me, this is blatant evidence that the future is queer.

These corporations follow the money, and with 20% of millennials and 31% of Gen Z openly identifying as queer, these businesses have to capitalize on the growing purchasing power of LGBTQIA+ consumers. With a recorded market size of $917 billion dollars in 2016, and a growing interest in socially conscious brands among young consumers, this is clearly a market opportunity that corporations cannot afford to ignore.

However, I'm always surprised by how little attention investors and the entrepreneurial community devotes to this undeniable trend, despite being constantly inundated with overwhelming statistics proving the importance of diversity and inclusion in entrepreneurship. Only 2.2% of venture capital funding went to women in 2018, less than .1% of funding has been allocated to black women since 2009, and only about 1% of venture-backed companies have a black founder or Latinx founder. These statistics are over-quoted but underacted upon.

This gender and diversity inequality significantly hinders economic growth, since 85% of all consumer purchases are controlled by women, and startups with higher ethnic diversity tend to produce financial returns above their industry norm.

The data is clearly leading to one direction: investing in women, people of color, LGBTQIA+ people, veterans, immigrants, and other minority groups in entrepreneurship leads to higher revenue and better business results.

As data-driven and forward-thinking as this industry claims to be, we haven't caught up to the queer founders, particularly queer women, who are rethinking the future. These founders understand and speak to a generation of increasing numbers of LGBTQIA+ people whose market share will only continue to grow exponentially. VCs and investors are already behind the curve.

Apply to pitch!

SoGal Foundation, a non-profit on a mission to close the diversity gap in entrepreneurship, is helping bridge this divide between queer women founders and investors with the launch of applications for the second annual Global Pitch Competition for diverse entrepreneurs. Hosted in 25+ cities across five continents, and culminating in a final global pitch competition and 3-day immersive educational bootcamp in Silicon Valley, this is the first and only globally-focused pitch opportunity for diverse entrepreneurs.

Startups that are pre-Series A (raised less than $3M) with at least one woman or diverse founder, apply here to pitch! The top teams selected from each regional round will join SoGal's final global pitch competition and bootcamp in Silicon Valley for guaranteed face time with dozens of top Silicon Valley investors, curated educational programming, unparalleled 1:1 mentorship, press exposure, and a chance to win investment capital.

Women, people of color, and LGBTQIA+ founders: what's the best way to kick off pride? Apply to pitch!

Regional pitch rounds will be held August-November 2019; final pitch competition in Silicon Valley in February 2020. Details and additional cities to be announced.


SoGal Foundation is a 501(c)(3) non-profit and the largest global platform for diverse founders and funders in 40+ chapters across 5 continents; our mission is to close the diversity gap in entrepreneurship. SoGal Foundation's global startup competition represents the first and largest opportunity for women and diverse entrepreneurs and investors to connect worldwide. Join the SoGal community & follow us on Instagram, Twitter, Facebook.