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Advice Etsy Small business Uncategorized

How to run a business without losing your mind: Coping skills for the small business owner

Jake's dog Ruby

My name is Jake Phillips. I’m the CEO of Whatify, an A/B testing tool for Etsy sellers that increases sales by up to 30%

Whatify is a startup — but not your open floor plan, free-lunch-providing, stylish silicon valley start up. More your “I work from home, my dog is my secretary, and I eat slices of cheddar cheese for breakfast, lunch, and dinner” startup.

Don’t get me wrong, I am not hating on it!  My commute is super short, my dog is really cute, and cheese is delicious! And when it comes down to it, nothing beats working for something that you truly believe in. However, I’d be lying to you if I said it was easy.  It’s not, and that’s okay. But that doesn’t mean I don’t do the things in my power to make these challenges a bit less daunting.

Jake's dog Ruby
This is Ruby. Ruby rocks.


To that point, I want to share with you, small business owner to small business owner, my tips for coping with the stress of the job that I am so lucky to have.

1. Sleep

You’ve heard the quotes:

“I’ll sleep when I’m dead” –The internet

“There will be sleeping enough in the grave”   –The internet

“Sleep is stupid”  –The internet

Alarm clock on bed

This one’s first on my list for a reason. For a while, these sayings would really stress me out. They added a layer of doubt, they added anxiety, they added another voice in my head saying “am I doing this right?!”

I now know that these sayings are mainly baseless cliches perpetuated by conniving competitors who are trying to drive you to make irrational business decisions! (I’m kidding… kind of.) The truth is that sleep is vital and getting the amount you need is crucial to your productivity.  

Seriously, sleep.

Science says that low levels of sleep impair attention, working memory, long term memory, and decision-making. It’s not like any of that is important for running a business, right?! Beyond that, lack of sleep can also lead to an increased risk of heart disease, high blood pressure, diabetes, anxiety, and depression. Solid.

Also, sleep feels great. And dreams are really cool! So when you finally lay down at 12:30 am, don’t turn on Netflix. You will thank yourself for it in the morning.

2. Ask for Help

Asking for help is important. Why?

  • No one knows everything, and people who pretend that they do are really annoying.
  • We live in the information age! Via the internet, we have access to endless data through our fingertips—might as well use it!
  • People like it when others ask them for advice—it’s flattering. When you ask someone for advice you boost their ego just a bit, which in turn, makes them think more positively of you.
  • Don’t just ask one person! Ask several, and consider their experiences when interpreting the information they provide. I like to take the consensus or “average out” all of the opinions I hear. If I hear something over and over again, I am a lot more confident that it’s legit.

3. Monitor Your Emotions

Emotions are weird. On one hand they are responsible for all of life’s joy and on the other hand they’re responsible for all of life’s sadness and frustration. That same dichotomy also applies to work.

It’s important for you and your staff (canines included) to maintain positive morale. According to the University of Pennsylvania, people in good moods “cognitively process more efficiently and more appropriately … and are open to taking in information and handling it effectively.” On the other hand, low morale results in less engaged, less productive employees. Employees who don’t feel positive about work do not feel internally motivated to commit causing them to call in sick and quit at high rates. So when someone comes to you with a personal issue, don’t dismiss it! While it may seem unrelated to their work, it could have a direct impact on their job performance. (It turns out that being receptive to people’s emotions is a key leadership skill.)

One great way to keep to foster positivity is to celebrate the little things. Go out for a beer at the end of a tough week or have a guilt-free facebook break after completing a list of tasks. Validating the small victories keeps teams motivated and focused on long term success.

Read more about why good morale is so important:

4. Trust Your Gut… Sometimes.

Human intuition, otherwise known as that “gut feeling”, often gets a bad rap from analytical types like myself. However, the gut can actually be a powerful and effective decision making tool in situations where empirical data is not abundant. According to psychologist Daniel Kahneman, human intuition is “highly adept [at] automatically and effortlessly identifying causal connections between events.” As a result, your gut can come in handy when you’re forced to make a quick decision without all the facts at your disposal. That’s why I keep mine happy be feeding it ample amounts of cheddar cheese throughout the day.

Watch out for Bias

On the other hand, human intuition certainly has a darkside. In his book “Thinking Fast and Slow”, Kahneman goes on to say that intuition often identifies connections even when those connections don’t exist.

In a small business, this is where things can go wrong. When we have a certain gut impression or feel a certain emotion regarding a decision, we are often slow to change our minds—even in the face of clear evidence. This can cause us to jump to conclusions and cherry pick data to support our preconceived notions. This is why it is vitally important to be aware of your emotional state while making a decision.  If you are personally or emotionally attached to an idea it can make you much more resistant to feedback and much less open to changing direction in ways that may be beneficial to your business.

For me, sometimes just being aware of these emotions is all I need to reframe the situation from a more objective perspective! In tougher situations, a few deep breaths or a walk around the block does the trick as well.

5. Make Time For Yourself (Work-Life Balance)

Do the things you enjoy.  Not taking time off from work can lead to a phenomenon known as “ego depletion,” a reduction in performance that can occur after long periods of sustained work.  Science says that “self-control or willpower draws from a limited poor of mental resources.” Working  60+ hour weeks can cause these resources to be drained. This reduction in willpower can cause business owners (like you and me) to make impulsive decisions that may impact your  bottom line. This won’t just affect your business! It may make it harder for you to curb other impulsive behaviors, such as eating entire sleeves of oreo cookies.

Plus, while most of the time it feels like your entire world revolves around your business, it’s still important to check in with yourself and have some fun. So my advice to you is to RECHARGE! How you go about that is up to you. Whether it’s cooking dinner with friends, going for hikes in the woods, doing yoga in hot rooms, I don’t really care. Just do it!

You might be wondering: How do I know if I need to recharge?

Great question! All I can tell you is how I know when I need to recharge. I start to feel emotionally depleted after too much hard work. This depletion results in the following symptoms:

  1. Depressed mood
  2. Lack of motivation to go the extra mile
  3. Restlessness during the workday

When I feel these symptoms I know for sure that it’s time to chill and take a step back. For me, recharging is often as simple as taking a hike in the woods with my girlfriend, catching up with old friends, or watching Curb your Enthusiasm with a bottle of whiskey.

Couple walking urban street

6. Verified Objectivity is a Gift, Use it (and Whatify)!

Our jobs would be a whole lot easier if there was a one-size-fits-all formula for running a business. We could just plug our information in and get the answer that would lead to our inevitable success. I wish.

The reality is that running a business floats in the nebulous world between science and art. Decisions are made when information is incomplete and when emotions run high. Confronting this uncertainty can lead to even more stress, making it even harder to make fully informed decisions!

Okay I’m starting to stress myself out. I might need to…

Take a nap.
Ask for help.
Check in with my emotions.
Recharge.

Again and again, these techniques have helped me maintain clarity and peace of mind through my most stressful and subjective times as a manager. To reduce the frequency of these stressful situations, I seek as much information as I can prior to making a decision. While the data available to me is almost always incomplete, the more of it I obtain, the more confident I can be in my decision making.

How do you go about gathering information, You ask?

I make sure to collect and save as much data as I can on my business itself! There is no information more relevant to your business than that which was generated by your business’s activities. For example, we’re sure to track the reach, clicks, and sign-ups as a result of each ad we run. More broadly, we save all of our historical data to databases, which I access and analyze using a computer language called SQL. I then take that data and run it through statistical software that actually translates all of that data into useable information. I’ll weigh these insights against other considerations (advice from experienced friends, best practices according to industry experts, etc.) in order to make the most informed decision.

I love numbers.

My dependence on data is one of the core reasons that I’m so passionate about Whatify (and it’s SO important to be invested in your business and mission; it’s why we all do these crazy things in the first place, right?) I know that most small business owners, especially if you work through a e-commerce platform like Etsy, do not have access to databases, and do not have the time to learn SQL and/or statistical programming. That said, small business owners still need and make evidence based decisions about their business!

Whatify provides users with the gift of automatic, algorithmic decision making. It is an all in-one database accessing, information extracting, statistical programming decision maker that barely requires you to lift a finger! By automatically gathering data on your product images, we can tell you with scientific levels of precisions which of images will lead to increased sales. As a result, there’s a whole set of stressful, uncertain decisions that you no longer have to make without having to invest in expensive software or learn how to code; and you can focus on other aspects of your business.

And hey — you can use the extra time for some other important decision, like whether to nap, shower, or eat more cheese.. Don’t worry — we’ve got this.

Jake's dog ruby looking at the camera
Ruby believes in us.

4 comments on “How to run a business without losing your mind: Coping skills for the small business owner

  1. Love this post. A clean and honest style, which gives authenticity to the subject.

  2. Thank you, Laura! Sometimes my honesty/authenticity gets me in trouble but I am glad that you enjoyed it in this case. 🙂

  3. Love the blog, but can we talk about that DOG 😍

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