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The Blogger Genius Podcast with Jillian Leslie

Mar 6, 2019

If you're interested in how to overcome burnout as an entrepreneur, this post is for you.

Most people outside of the online world have little understanding of what being an entrepreneur entails.

Sharing with your friends or even family that you’re struggling with blogger burnout may not bring much relief. It’s not that our people don’t want to help us; they simply don’t know how.

Most folks have never spent months or years trying to get a business off the ground. They don’t understand the pressures of building a business and what it requires of you day after day and year after year. And so they simply can’t offer any solutions to the all-too-common struggles of entrepreneur burnout.

This is a topic that’s near and dear to my heart. My husband, David, and I have built 2 businesses from scratch, so we know what it means to face the daily slog of a mile-long to-do list and too few hours in the day to get it all done.

That’s why I am so excited about my guest on today's episode of The Blogger Genius Podcast, Jason Zook.

Jason Zook has started some of the most unique businesses I have seen. He and his wife Caroline have a membership site for client-based business owners who want to begin developing and selling digital products but not burn out while doing it.

Jason has some interesting thoughts about when enough is enough in your business.

If you suffer from blogger burnout, entrepreneur burnout, etc., his method will help you set new guidelines and reshape the way you think about your business. I think you will find him incredibly inspiring.

How The Purple Cow Changed Things 

Jason began his entrepreneurial journey in 2007, with no background in the sphere, not even a lemonade stand as a child.

He had a normal 9-5 job as a graphic designer for three years after graduating college. But one day he looked around and realized how blah his existence was. He felt that he was surrounded by beige, literally and metaphorically.

Then one day, a book, The Purple Cow, landed on his desk. That book helped Jason see himself in a new light and propelled him to make the leap to something new.

He began his own design company with a friend, and they grew that company over the next two years. In 2008, he was standing in his closet when he realized that he was promoting businesses just by wearing shirts with their logos on them.

At that time, social media was only just beginning to emerge and Jason saw an opportunity to use that platform in new ways.

He created a project called, I Wear Your Shirt. For one year, he was going to charge small businesses to wear their shirts and promote them on social media.

It was not an easy road to pursue, but he knew he wanted to do something unique. That project went on for five years, and although he ended up with debt in the end, he will forever have the lessons he learned from that time.

All the time, people are having those ideas that make you say, “Why didn’t I think of that?”

Jason did the same with his tee shirt project. Even though it ended in 2013, his project still gets fresh traction because of its bizarre nature.

Learning Through The Challenges

Not knowing how to run a business perfectly, the unusual charging structure for the project, and taking on too much growth too quickly made it hard for the business to stay afloat.

Jason says that he was focused on growth and success the way he saw it playing out for others.

The problem is that what works for others doesn’t always fit your particular business. Without knowing how to manage the day to day of expenses and revenues, Jason was getting deeper and deeper into a hole.

It sounds silly to say that he didn’t think about how the business would pay for itself, but no one gets taught this in a way that is applicable to entrepreneurs. Jason helps many entrepreneurs work through problems they have keeping their businesses afloat.

Business classes are not focused on entrepreneurial business. Without knowing what things to look out for, it’s easy to get swamped before you know it.

Jason had several credit cards, he owed family money, and when he realized he was over $100K in debt, he made the decision to throw in the towel. He worked tirelessly for five years and ultimately, the entrepreneurial burnout he faced forced him to take a break and reevaluate what he was doing.

How to Know When to Quit Being an Entrepreneur

Jason’s business with his wife is the climax of all they have learned throughout their business careers. He says that it all boils down to knowing who you are. Are you an entrepreneur? Are you cut out for that kind of life?

9-5 jobs are very straightforward. You have a set path that you follow daily.

Entrepreneurs do not have that safety net.

You are going to have unknown expenses; your path might change from what you originally planned. If you think you want to start a business, you need to know a few things going in. The first is related to the choices you need to make.

You have two choices.

One, you can give yourself a cap on how long you can stick with your idea. You might have enough savings to get you through six months or you might be willing to go a couple of months incurring debt.

Choice #1 is to give yourself an end date. Decide to stick with your project for say, one year. At the end of the one year period, you have to reevaluate on whether you can keep going.

Choice #2 is that you have to know at what point you will decide to stop with the project and move on for your own good and your family’s good. You need to cut your losses at some point. So if you see your business isn’t heading in a positive way anymore, it's time to cut your losses and move on to something else. 

When Failure Is What You Need as an Entrepreneur

Jason struggled with feelings of failure until he read Ryan Holiday’s book, The Obstacle Is The Way.

He learned that the business failing is what needed to happen for him to learn lessons about business, entrepreneurial experiences, work-life balance, and debt.

If he hadn’t stopped when he was $100K in debt, he may have gone on until he was $1M in debt. That $100K became a boulder he had to get around, but it helped give him a better focus on budgeting.

When something doesn’t happen the way you think it will or a project fails, it’s your chance to reframe your thinking to, “This is an opportunity for me to get better and learn something.”

Outsourcing Your Weaknesses as a Blogger

It is hard work to be an entrepreneur. You have to make sure you hit every area of your business to make it grow and become better. For some of us, it’s worth it.

But you have to know if you want it and how badly you want it.

For Jason, paperwork is a weakness. He would rather clean house than do paperwork. So it is worth it for him to hire a bookkeeper to do that.

Focus on where you might need to bring in strength from outside in the areas you lack it. Jason encourages entrepreneurs to find the three things they absolutely hate to do and then see if they can outsource them for under a couple of hundred dollars a month.

Doing this one small thing will free up your time and your energy, including your mental energy.

*Here at Milo Tree, I tell people to figure out what you make an hour, and if you can outsource a few jobs for less money than you make an hour, you should do it. Some things are more expensive, but freeing up your time and releasing yourself from a task you despise is worth it. If a job is holding you back and hindering your business growth, you need to outsource it.

I go to UpWork and I hire people for a specific project. If we work well together, we can do more projects in the future. I have met so many wonderful people just by doing that.

How Much Is Enough?

The media has glamorized having lots of employees but in reality, it is stressful. Jason learned from his failed business that he doesn’t need to bring on help just for the sake of bringing on help.

You have to put yourself in the mindset of asking, “How much is enough?”

Jason and his wife ask themselves this question to ground themselves.

How much money does a business need? Not how much money is a glamorous number, but how much would you really need to survive? Break down why you want the number that you’re going after.

Jason has an MMM number, “Monthly Minimum Magic” number. That would be the money it takes to survive and run your business. No matter what, you want to make that.

Then you can pick your “Enough Number”, the one that gives you all that you need. This is the number that provides abundance, the number that makes you feel like all the work you put in is worth it.

If you can pick a number, you will free yourself from having goals that are unattainable and discouraging because they are too big.

Minimalism is everywhere now. People are starting to embrace the idea that enough is enough. Reaching your number may take time, but it will be achievable if it’s not some pie in the sky arbitrary number.

Taking Control of Your Perspective

Instead of focusing on things that you believe will make you good enough, like an annual income, focus on how far you’ve come.

Focus on how much you’ve learned. You can celebrate the small victories and not put all your hopes of happiness in future accomplishments.

When you’re stressed and overwhelmed, you can take a moment to realize how far you’ve come and how your hard work is paying off.

Jason says he is, “Walking a business, not running a business”.

He and his wife got tired of always feeling like a hamster on a wheel, running with no end. All of this constant running, from emails to calls to meetings to social media to more emails...this is what leads to entrepreneurial burnout.

Why can’t we just slow down to a walking pace? We don’t have to run all the time. It’s okay to slow down sometimes.

Sometimes you have to run to get started, run to a place where you can walk, but if you’re thinking about what you would like to achieve, once you hit that, you can give yourself the freedom to rest more.

The Concept of Time Profitability

In business, it’s easy to understand cash profitability but we don’t think of time as something that offers profitability.

If you have certain goals, are you willing to be time poor while you’re pushing yourself to reach those goals?

Even if your business makes less money than you think it should, are you getting more time? Are you able to enjoy an easier schedule while still making enough?

Jason likes to challenge the idea that money is the only profit you should think about in your life.

Most people have to learn their lessons themselves. You might get to a certain point and realize your time isn’t as profitable as it could be.

Do you have a tendency to always think that you’re falling short in what you do? We have to overcome those ideas of what’s normal for us so that we can go at our own pace, enjoy the moments in life as they come, and not feel burdened to always be running.

No season in life will last forever. It’s important to make sure that you have a balance so you don’t miss out on life while you are building your business.

Jason likes to ask, “What is it all for?” He knows that he cannot sacrifice the now in the hopes that when he hits his goals someday, that will fulfill him and make him happy. Your problems aren’t going to go away if your business succeeds; you’re going to have more of them.

If you pursue more than what your enough number is, what are you going to have to sacrifice to get there? Is that money profit greater than your time or peace profit?

Jason identified what was important in his life, and now he can work through the stress of running a business, because of the life he now gets to live. A life without burnout and without regrets.

How to Know When You’ve Made It as an Entrepreneur

Jason was able to identify when he felt that he had “made it” because he wasn’t constrained by what society said success is. He has what he wants and he is happy to have it.

When you are able to identify the things you want from life and what is enough, you can be content, knowing you have gotten what you desire.

As an entrepreneur, you not only need to manage the books but you need to manage your own brain. You need to manage the stories you tell yourself. You can tell yourself when you’ve made it and that’s okay.

You don’t have to keep grinding forever and forever. You can have enough and be happy in the life you want.

The finish line is whatever you want it to be.

Overcoming Burnout as a Blogger

Jason definitely struggled with burnout after the completion of his I Wear Your Shirt project.

He had filmed himself almost every single day for 1,600 days straight. This was before Youtube stars and daily vloggers were really a thing. For 4 years after the business ended, he couldn’t stand to look at a camera.

Anyone who’s gone through burnout knows that the only thing that heals it is time. You need space away from the things that burned you out so you can come back to it.

To handle the burnout, you can set parameters to help you do the things you need to do. More relaxed schedules and less comparison are some of the things you can put into effect so that you won’t feel soul-sick while working.

Jason has created a six-month program called, Build Without Burnout Academy, to help people who want to create a digital product of some kind. This program is releasing in March of 2019.

It takes a lot to get something up and running and making revenue, and Jason helps with doing all of that while keeping the burnout away.

His method, based on his experiences, helps you set goals you can achieve, take your time doing it, and not hate every second of it. It is very important that you don’t get burned out building a business that you are then going to have to keep up and running for years.

There Is No Magic Bullet to Growing Your Online Business

We tend to buy into the idea that a quick fix is all we need to be making millions of dollars.

What happens when that doesn’t happen?

We hit burnout. It is so important to have realistic goals, visions, an idea of what you will have to sacrifice, and how long it might take. You have to be willing to not sacrifice yourself and your life on the altar and grow your business in a way that you will be happy with.

There is no magic bullet for success. It’s a day in and day out grind. But you get to decide what that looks like for you and how you can make it fit the life you want to be living.

You can learn more about Jason and Caroline and listen to their podcast on Jason Zook is on Twitter and Instagram as well. Jason would love to connect with anyone who is ready to build a business they can enjoy running while living the life they want to live.


  • Intro
  • 1:00 How A Purple Cow Changed Things
  • 6:05 Learning Through The Challenges
  • 10:34 How to Know When to Quit
  • 13:08 When Failure Is What You Need
  • 16:00 Outsourcing Your Weaknesses
  • 20:30 How Much Is Enough
  • 24:00 Taking Control of Your Perspective  
  • 26:58 Time Profitability
  • 32:02 How To Know When You’ve Made It
  • 38:13 Overcoming Burnout

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