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4 Expert-Backed Strategies for Making Difficult Decisions

Gaining greater perspective will help you confront insecurities head on.

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Eric was one of the most fearless entrepreneurs I'd encountered. His prowess when it came to making calculated decisions was unparalleled. When faced with difficulties, colleagues would often flock to him for counsel.

There was just one area where Eric deeply struggled with indecision: public speaking roles.

As you might guess, this hindered him from taking on more valuable opportunities. Even as he could relay his thoughts one-on-one and in emails, if he had to choose between taking on a more senior role that involved public speaking or staying put, he would often procrastinate.

Whether you're starting your business or are a seasoned entrepreneur, if you find decision-making challenging, here are a few different ways you can approach it, according to experts and my own experience.

Learn your triggers

Executive coach and author of The Art of Decision Making Joseph Bikart argues that one of the reasons certain decisions can be so difficult to make is because they trigger scary memories. "For example, a decision might unconsciously reignite a past traumatic event and alter your judgment as a result."

In Eric's case, his fear of public speaking stemmed from an incident in middle school where he endured humiliation after a disappointing speech. Which is to say, his indecision all these years later correlates to this one specific event.

That's why as Bikart points out: "It can be tempting to take the easy road and procrastinate."

I know I've done this myself. As a bootstrapper, I had to teach myself to push through procrastination. But in order to do so, I had to identify the underlying problem — get to the root of the issue. Why was I avoiding certain tasks?

When I looked beneath the surface, I realized that I was terrified of making a bad decision. I was also caught up in an endless cycle of perfectionism, which also hindered my progress. Meanwhile, like Eric, I was missing out on opportunities to grow my company and forge better business partnerships.

Recognizing my fear of failure helped me make the distinction between who I am versus what I achieve.

One of the things I learned in building my business was that stalling only held me and my team back. "Moreover, indecision and procrastination do not postpone the pains of a decision to a future day," writes Bikart, "they multiply that pain by spreading it across every minute of every day, until you finally decide."

Related: 3 Simple Tactics For Making Better Choices

Listen to your gut

This isn't to say you should throw rationale out the door, but there's a lot to be said for weighing your decision-making on a deeper sense of intuition. "When dealing with difficult decisions, then, learning to listen to your emotions and feelings is a powerful indicator of what you truly aspire to," writes Bikart.

Contrary to popular opinion, researchers have found that "intuition or gut feelings are also the result of a lot of processing that happens in the brain," Valerie van Mulukom writes for BBC Future. "When you have a lot of experience in a certain area, the brain has more information to match the current experience against," she adds. "This makes your intuitions more reliable."

For example, since launching my company back in 2006, we've added hundreds of staff, opened three offices on two continents and built a product with 10 million users. I mention all of this because I've learned a thing or two when it comes to evaluating people. When hiring, for instance, my gut instinct informs a lot of my decision-making — in large part, because of the years of experience accumulated recruiting and understanding what kind of candidates make the best fit for my organization's culture.

Related: 7 Keys to Making the Right Decision the First Time and Every Time

Use the baby steps approach

One of the biggest reasons Eric struggled with procrastinating when it came to public speaking roles is because he didn't know how to act upon his fear.

Breaking down these big decisions into baby steps allowed him to start making progress where it used to feel impossible. Here are a few of the solutions he found to be helpful in overcoming his indecision:

  • He joined a public speaking class to help him eliminate anxiety in a smaller-scale setting.

  • He worked with a coach to help him identify triggers and work through unhelpful memories.

  • He reached out to trusted friends and contacts who would offer him feedback in a positive and constructive environment.

I'm happy to report that all of these micro-steps created momentum and gave Eric the confidence he needed to take on more public speaking roles — increasing his company's opportunities and overall success.

Related: 6 Common Decision-Making Blunders That Could Kill Your Business

Get greater perspective

Probably the most surprising thing I've learned in my research about decision-making is that avoiding making a decision, is in fact a decision. Albeit, the wrong one.

So how can we take a step forward in the right direction?

Something that's helped me over time to gain greater perspective is spending at least an hour every day writing morning pages. It's a daily routine that helps me clarify my objectives, list out my feelings and identify why some decisions are harder than others. Taking this time to self-reflect allows me to think outside the box, imagine new options and confront my insecurities head-on rather than cower from them.

Another strategy I've used is billionaire Warren Buffet's 10/10/10 rule, which comes down to asking yourself these three key questions:

  1. How will this decision make me feel in 10 minutes?

  2. How will it make me feel in 10 months?

  3. How will this decision make me feel in 10 years?

So, now the most pressing question of all: How does all of this apply to you?

Because it forces you to think further ahead, to assess the emotions that arise and your immediate reactions to the answers. With constant practice, not only will thinking ahead benefit you in the long-term, but you'll also be more aware of the bigger picture and what it is you truly want.

Related: How to Harness the Power of Macro Decision-Making

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