top of page

The Complete Guide: How To Make Tough Decisions

I recently had to make a tough decision. Faced with a family tragedy I had to decide if I was going to drop everything and fly halfway across the world to be with my family.

While theoretically, this decision should be a no-brainer, it wasn’t an easy one to make.

I was in a critical stage in my business and had a few big projects scheduled.

Flying on a moment’s notice was going to be expensive, not to mention it’s a 24 hours trip. Not easy.

I had a vacation planned a month and a half later - which meant I would be seeing my family soon enough.

It took me a full day to decide I’m going to jump on that plane, no matter the cost.

Here’s how I finally made a decision. I used a framework called regret minimization.

Regret Minimization

According to the FourWeekMBA: ” A regret minimization framework is a business heuristic that enables you to make a decision, by projecting yourself in the future, at an old age, and visualize whether the regrets of missing an opportunity would hunt you down, vs. having taken the opportunity and failed”.

This technique has been made popular by Jeff Bezos.

Faced with a tough decision I asked myself: A year from now, would I regret not going?

The answer was YES.

The more I thought about this question as my future self, the more it became clear how insignificant the immediate consequences were in the long run. I will never have this opportunity to support my family again, but I would always be able to develop new business opportunities.

At that point, the decision was made and I booked my flights.

Looking back now I know it was the right decision because I have no regrets.

You can use the Regret Minimization framework to make tough decisions about your career and life. You can answer questions like:

  • Should I ask for a raise?

  • Should I apply for a promotion?

  • Should I pivot?

  • Is it time to change employers?

You can also use it to make decisions like moving your family to a different state, writing a book, or launching a podcast (shhh.... it's still a secret).

Would It Move Me Toward My Goals?

There is another tool you can use to make tough decisions.

A few years back I was working for Microsoft, arguably one of the best companies in the world. After 2.5 years with the company, I felt like I was ready for a promotion, so I started the process of interviewing for a skip-level role. I was so excited about the possibility of getting more responsibilities and a nice raise.

As a rule of thumb, I always explore more than one opportunity. I want to know what are my alternative costs, and what I may be passing on if I choose to stay with Microsoft.

That meant I started interviewing externally as well. At first, I wasn't sure what to look for, but after sending out a few emails to my network I was introduced to a startup CEO who was looking to hire a marketing leader for their company.

I ended up having to decide between two options: take a more senior role at Microsoft or join an early-stage startup.

On paper, Microsoft had more to offer:

  • Bigger compensation package

  • Amazing perks

  • Job security

The startup role was a bit risky:

  • Decent yet lower compensation package

  • A lot of uncertainty

  • a lot of hands-on work

I had to make a tough decision.

I could stay with Microsoft and get a promotion that included a big raise, more responsibilities, and amazing benefits, or I could join a small startup, and start as the only marketer to earn my way to the top.

If I was just using a pros and cons list, I probably would have stayed at Microsoft. But instead, I asked myself one question: Which option would move me closer to my goals?

My 10-year career goal at the time was to become the CMO of a Silicon Valley startup. I wanted to lead marketing and get closer to the business side.

When I asked myself which role will get me closer to achieving that goal, the answer was obvious. I was going to take the startup route.

If my goal was to build wealth or buy a house in the next few years, I would have stayed with Microsoft. There is no "right" answer, it really depends on what you are optimizing for.

Make Tough Decisions With Confidence

Every time I had to make big career decisions I’ve used one of these questions to help me gain more clarity. When I made the decision to leave my 9-5 job and start my own business I used both frameworks to help me decide. I knew I would regret not starting a business, but asking myself what would get me closer to my goals made it clear the timing was now. So far, I have no regrets about this decision 💪.

Next time you are faced with a hard decision try asking yourself:

1. X weeks/months/years would I regret this decision?

2. Which option would move me closer to my goals

These simple questions would add more clarity and help you make a tough decision with confidence.


Level Up Your Career With One Email Per Week

Get practical and actionable career advice every Saturday so you can level up, earn more and grow 3x faster!

Stuck at the Director level for 2+ years?
Tired of being told "you are not ready"?

Learn how to break through to executive roles without the complexity and overwhelm, or working 60/h weeks 💪

Check out my proven 13-week coaching program Success Builders to turn your career goals into reality.

bottom of page