Do You Dream About Telling Your Boss You're Quitting?

F*** this, I’m quitting now!

We all dream about the day when we can tell our boss that they can take their demands elsewhere because we are no longer working for them.

We see that meme about the guy tossing paperwork everywhere at an office and we get a warm fuzzy feeling.

Is this really the best thing that can happen to us?

Is our life so miserable that we cannot wait to quit or end what we are currently doing? What kind of life is that?

It is true that life is not fair nor easy. Yet, there should be some joy in the process. If we are not having at least a bit of fun then we are doing something wrong.

Sometimes the best thing to do is say NO and don’t even start.

But in order to grow, we have to say YES to the opportunities that show up. This is something we all struggle with. How do we know we are saying yes to the best possible opportunity?

Which schools should I apply to for my MBA?

Should I take this offer from company “X” or should I go to company “Y”?

Also, once we say yes how do we keep the momentum going so we can grow and learn as much as we can?

Maybe at some point, you might even need to quit because that is the best possible decision.

Some people say that in life we only have three choices:

  • Accept
  • Change
  • Leave

Over the next few weeks, Matt and I will explore these topics to help you make better decisions.

We will share with you what we’ve learned by studying how successful people make decisions, the processes we have used that have lead to successes and failures, and how to cut those losses short when it’s time to move on.

Now let’s explore the process of deciding what and when to start new ventures or challenges.

Knowing if You Should Start is the Hardest Decision


Don’t buy into the hype of a new venture.

It’s easy to fantasize about the new job, graduate program, starting a business, launching a blog, or anything else new. The thoughts flood in, you will be a rockstar the world has never seen before as you take on the new role.

6-months later and reality hits you hard. Elon still hasn’t invited you to his private island, everything is more difficult than you thought it would be, and for some reason, your new project is taking longer than expected. I know all of this because I am guilty of starting too many projects.

There are the multiple startups I have worked with, Law School (never graduated), the job I took for equity (FYI 6% of $0 = $0), working for free, moving to a new city, and the list could go on . . . and on. For some reason I am extremely steady in my decisions except for massive life-altering choices, then I jump head first, most of the time it ends in complete failure.

My biggest area of expertise is in making bad decisions, especially because I get excited in the potential outcome. Perhaps you are the same. The new job offer looks amazing, going back to school will change your career, or your side hustle is going to become viral.

Now, let’s be clear, sometimes change is exactly what we need. It is time to take a new job, attain a graduate degree, move to a new city, or start something on the side. Yet, those moments of changing your life should only come after knowing what you really want.

Let me explain. I have been an internship leader for a non-profit, taught at the college level, and now, work with small businesses to improve their marketing. Over the past decade, I have seen a trend in the people who succeed in new ventures. They have clear goals and metrics for success.

  • Do you want a new job?
  • Do you want to go back to school?
  • Do you want to invest in a company?
  • Do you want to launch a company?
  • Do you want to move?

Before you answer any of those questions, simply ask yourself, why? You should be able to clearly articulate your reason for making a change. Moreover, your explanation should easily be explained in a single sentence. Don’t answer the “why” question with a rambling paragraph. Your answers should be clear and concise.

Instead of imagining a hypothetical future, you should really visualize your decision and have a rationale for the choice. Don’t get me wrong, a good answer could be “I am ready to take a risk and move beyond my comfort zone to test whether I can build a business or not.” That’s a good reason to start your own thing, but notice it’s clear. A bad answer would be “I want to be my own boss and not listen to others.” Newsflash, being an entrepreneur means you work for all your clients, customers, and employees. Notice the difference, in the good answer, there is clarity of doing something to prove oneself, in the bad answer, the motivation is anger with a boss.

New opportunities will continuously arise if you are a high-achiever, and if you are reading this, you likely are someone who reaches for excellence. You should only take on new ventures when you can explain your reasoning. Otherwise, you could lose money and time, experience bad failure (there is a difference between bad and good failure), become bitter, or lose friendships.

Really think through your “why” before jumping into that new experience.


As humans, we have mastered the art of letting our losses run and cutting our winnings short.

This is because we do more to not lose than to win. Avoiding the pain of losing incentivizes us more than the joy of winning.

Once we are aware of this bias, we can actually use it to our advantage. We will explore this throughout the article.

Also, it is key that you always begin with the end in mind. Visualize how you want to finish, with a clear understanding of that growth that will take place while taking action.

When you are curious, everything seems like an exciting opportunity!

Beginning with the end in mind, and having a clear picture of the overall process, might help you avoid jumping to quick into all the opportunities that show up.

Are you the type of person that goes all-in into everything that you are currently doing? Maybe you end up being good at many things but not great at any.

This might be what is holding you down from making it to the next level.

Whenever you are thinking about starting something new, two fundamental questions that can help you make a better decision are:

  • Will I get to develop or master a skill?
  • Will I build meaningful relationships?

It is key that those skills or relationships are aligned with a bigger goal.

Get involved in activities that will allow you to grow your skills and your network. This applies to everything you do.

Do you want to join a gym? Make it an effort to connect with people there.

Do you want to volunteer at a non-profit organization? Be sure to do so in a way that will allow you to tell a good professional story after you finish.

Even if you decide to take a sabbatical and travel the world. You should already have in mind how are you going to tell that story when you decide to come back to the workforce, or how will you leverage that to start a business or grow a following.

Every Step Should Have a Purpose.

Once you do that then you have a clear idea of what you want to achieve then you have to ask yourself: Are You Willing to Do What It Takes to Make It Happen?

For example, getting a website to start showing up on Google searches can take up to 6-months. So if you are not willing to put the work for at least 6-12 months then you shouldn’t even create a website.

If you to invest for when you retire you should have an emergency fund so that if something happens you don’t have to take your money out of your investment account when the market is down and you lose money.

You could get an idea of what it takes to make it happen by having informational interviews with people who have “been there, done that”. This will allow you to save a lot of time and energy.

List Out All the Possibilities!

This is something that separates the good from the great chess players in the world.

The best part is that we can apply to any type of decision making.

What they do is that before making a decision, they go through all the possibilities but without exploring them deeply.

The first step is to list them out, then eliminate the ones that clearly are not good ones. Then you go deeper into the ones that seem to be the best ones.

The mistake we often make is that we list a couple of options and then we start exploring deeper into those options. By the time we are done with A and B we have no energy to think about options C, D or E.

For example, if you are thinking about starting a new business the scenarios could look like:

  • What if we don’t sell anything for a month
  • What if we don’t sell anything for 6-months
  • What if we don’t sell anything for a year
  • What if we sell everything in a week
  • What if we sell everything the first month
  • What if we sell only “X” for the first 6-months
  • Etc.

This process will allow you to identify your weakest points, or the biggest risk, and how to minimize these. Tim Ferriss shares a process like this in his latest TED talk.

To summarize:

  • Begin with the end in mind
  • Understand the purpose of each step
  • List out all the possibilities

Big Decisions Require Clarity 

We want you to be excited about new opportunities. Making changes and stepping out of your comfort zone our the first steps to finding your definition of success. 

However, we are cautioning you to think through the decision and ask yourself clarifying questions before going all in. You wouldn't climb Mount Everest without prepping first. The same is for your large decisions. Take the necessary time to really think through the outcomes and why you are making a change. 

We are here to help with this decision making process. Join others who are defining and achieving success on their own terms with our free monthly resources.