Stop Overthinking Business Decisions

November 22, 2019

By Mariana

My name is Mariana and I am an overthinker. 

Do you overthink overthinking?

I am naturally analytic and strategic, but overthinking is good thinking gone bad.

Do you tend to overthink decisions in your business?

Merriam-Webster defines overthink as “to put too much time into thinking about or analyzing (something) in a way that is more harmful than helpful.”

Essentially, it’s repetitive or obsessive thinking that is not productive.

Overthinking takes us from considering to confused.

Confused by over complicating a decision.

Not sure you’ve been overthinking?

Here is a quick overthinking self-assessment:

◼ Do you find it hard to make choices, even “easy” ones?

Do you miss out on opportunities due to issues with deciding on a direction to take?

Does your mind become clouded with doubt and fear when faced with a decision?

Does your brain provide a list of imaginary issues and non-existent obstacles?

Does making decisions leave you feeling overwhelmed and stuck?

Does answering these questions cause smoke to come out the top of your head?

Chances are, that if you answered yes to one or more of these questions, you’re an overthinker. 

It’s a sliding scale from delayed decision making to analysis paralysis.

Sidenote: Analysis paralysis refers to a situation when someone is unable to make a decision due to over-analyzing data or overthinking a problem.

Common things people overthink:

  • Situations
  • Opinions
  • Decisions
  • Opportunities
  • Choices
  • Actions
  • Lunch << Can result in HANGRY situations 

Overthinking can become our natural response when faced with decisions, which is not good for us or for business. 

It doesn’t just cause furrows in our brow or burn our precious brainpower, research shows that it is linked to:

  • sleepless nights
  • depression
  • increased negative self-talk
  • impaired problem-solving << Kind of counter-productive right?

As business owners, the biggest negative impact is, it prevents us from taking action and moving forward.

I want to help you break out of the indecision rut.

Below is a series of steps to help you beat analysis paralysis and take action. 

Now, before you start overthinking your overthinking, we better get started.

The Overthinker’s Analysis Paralysis Remedy

Here’s a handy-dandy workbook of this remedy for you.

Own It

What is the problem, opportunity or decision that you need to resolve? You can’t solve a problem or make a decision without clearly defining it.

We need to focus your brainpower on a singular point. Otherwise, you can fall victim to tangents and squirrels. 

Catch and release

Those voices in your head that have opinions about everything are not helpful.

A helpful exercise is a brain dump.

Grab a piece of paper, jot down all the thoughts and then examine them with fresh eyes. 

For each item, ask yourself whether it is helpful or not. 

With a black marker, cross out anything that isn’t helpful. As you do this take a page from the book of Frozen and “Let It Go.” 

With another pen (color of your choosing), circle the items that are worth considering for the decision at hand.

For larger decisions, you may need to repeat this exercise again if you find your mind becomes a swirling vortex of unhelpful thoughts. 


Let’s put things into perspective. 

Sometimes small things can seem like big things once our busy brains get ahold of them. 

Take a moment to anchor this decision in your business goals and the big picture. 

For example, deciding on which accounting software to use is a big deal, but it isn’t likely to cause the demise of your business if the first one you try isn’t a perfect fit.

A little perspective helps provide an escape hatch if your mind likes to jump straight to worse case scenarios. 

Sidenote: Don’t be afraid to reach out to somebody you trust to get help with putting things into perspective.

Drop the fear

Next, we need to come to terms with the possibility that whatever decision we make doesn’t turn out perfectly.

Fear of failure is often what keeps us stuck in overthinking and indecision. 

Giving yourself permission to make a “wrong” decision can create a crack in the fear.

Condition yourself to view the results of your decision, good or bad, as a learning opportunity. If you learn from the experience it isn’t a failure. 

John C. Maxwell’s book Failing Forward is a great read if you want to dig into this concept a little deeper.

When you release the fear of failure, plus add permission to learn and grow, you’re ready to go. 

Arm yourself

You need to figure out what you need to make your decision. 

Make a list of what you need to make an informed decision. 

This will help keep you focused as you look at options and filter through opinions.

A list like this also can create a structure to keep you from getting sucked down any rabbit holes.

Stop waiting 

Are you holding off on making a decision because the “timing” isn’t right?

The truth is that there are rarely perfect conditions for anything. Whether it’s having a child, starting a new healthy habit or investing in your business.

If you honestly don’t have the resources then maybe the decision is made for you, but if you have enough time, money, knowledge or whatever else, stop delaying the decision and get on with it. 

Decision deadline

Spending hours or even days gnawing on a decision is not an effective use of your time. 

To make sure you don’t get sucked into a rumination rut, create a self-imposed deadline for your decision. To be effective, you need to commit to this deadline. 

Determine how much time you need to make an educated decision and draw a hard line in the sand. 

Some decisions require more time than others but hold yourself accountable.

If you suffer from squirrel-brain as I do, I suggest you put on a timer to keep yourself squarely focused on making a decision. 

This works for larger decisions too. If you need to gather information over a few days, use the timer to create a structure for the time spent doing research.

Forest is a wonderful app and Chrome extension that I use when I need a timer.

It’s beautiful and effective. 

Decision time

You’ve done the prep work and now it’s time to make a decision.

Ideally, you want to crush your decision deadline. Don’t wait, do it now.

Write out what you’ve decided. Now own it. 

Doing this is a big deal if you chronically suffer from overthinking and analysis paralysis.

Take action

Turning the decision into action is where overthinking officially gets kicked to the curb.

It’s like an analysis paralysis eject button.

Eject your analysis paralysis.

Once you’ve made your decision, identify the first step and take it. NOW!

If you delay taking action, you risk sliding back into the murky waters of indecision and overthinking.

Do your best

You need to have faith in your ability to show up and do your best. 

The reality is that outcomes in business as in life are rarely 100% in our control. 

For A-Type personalities that can be a hard pill to swallow, but it can also be freeing. 

Knowing that you don’t have to shoulder and manage every moving piece of an outcome, means you can focus squarely on what is in your control.

Do your best.

Forgive and forget the rest. 

Reflect & Reward

This is often overlooked but is integral to developing your decision making muscle and breaking the overthinking habit. 

Once you’ve made a decision and taken at least one action step, it’s time to recognize this as a win.

Take a moment to reflect on the process and what you found helped the most. Do a happy dance or eat chocolate. 

You can also eat chocolate while doing a happy dance. 

Breaking free from overthinking isn’t hard, but it isn’t always easy either.

However, with this remedy on hand, you’ll be able to navigate even big hairy scary decisions and sidestep the analysis paralysis.

Not all your decisions will be stellar, but at least you will make them, take action, learn and keep growing. 

Snag a copy of The Overthinker’s Analysis Paralysis Remedy Workbook

Keep a copy of The Overthinker’s Analysis Paralysis Remedy Workbook on hand to streamline your business decision-making process. 

What will you do with all the time you would have spent overthinking?

Hi, I'm Mariana.

Hi, I'm Mariana.

As you've probably guessed already, I'm the heart and brains behind The Purposeful Entrepreneur.

Supporting entrepreneurs and business owners while teaching and sharing lessons learned brings me joy.

I love family time and do what I can to make the world a better place.

I'm very fond of coffee and puns. I strive to live life to its fullest, grow a little bit every single day, and inspire others along the way.

Let's explore how I can help you.

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