How to Make Career Decisions That You Will Never Regret

Plot your career as a journey full of lessons and you will never regret a choice you make.

July 22, 2019 6 min read

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We often judge career decisions as good or bad by only evaluating the rewards the commitment brings. Money, status, networks, progress up the career ladder, decision-making power and degree of influence are classic feedback indicators we look to as success measures or lack thereof. Such external markers can lead us to make bad career decisions in many forms.

We often set goals that aren’t truly our own, listening to the advice of those who aren’t qualified to give recommendations and directions. In a bid to belong and feel accepted by our friends, family and our dependents, we’re on track to carve out a lucrative career, but inside we’re utterly void of work and personal satisfaction. Regret underpins the ‘should have,’ ‘would have’ and ‘could have’ internal dialogue that plays when we’ve made such decisions.

Plot your career as a journey full of lessons as opposed to a final destination and you will never regret a choice you make. You’ll be apt to take greater leaps, considered risks and feel grateful for every trial and tribulation along the way. Hindsight will always be a beautiful thing.

1. Devise a career map, not a single trajectory.

Waiting for the next carrot to be dangled to then decide if you like it or not means you’re not in charge of determining where you’ll end up. To minimize your chances of making regretful decisions, start with a review of your journey thus far and ask yourself the following questions:

What has been my most enjoyable experiences and what made them so enjoyable?
What sort of people and relationships have I learned the most from where the lessons were most valuable?
What environments provided me the best learning opportunities and experiences? What features of those environments afforded me this?

The answers you uncover will strengthen your awareness and clarity around what you truly want and help your reticular activating system filter for opportunities that take you towards finding it. Create your own decision-making opportunities rather than allowing someone else to dictate your direction and progress. Also, don’t just think of the next conventional linear rungs on your career ladder. Be enlightened to step sideways.

As Benjamin Hardy was undertaking his organizational psychology Ph.D., he started writing projects on the side. After eighteen months of continuously improving his penmanship on Medium, he became the platform’s most popularly read writer. From here Hardy was inspired to develop his first online course which generated just short of one hundred thousand dollars during the first seventy-two hours of its launch.

What followed was Hardy sought the services of a proposal writer to help him land his first book deal which won him a three hundred thousand dollar grant to pen Willpower Doesn’t Work. Hardy is indeed now a renowned, published writer and author across different mediums: online courses, books, psychology-focused research articles and featured guest writer.

All of these pathways led to Hardy doing what he wanted to do, be and have. Note, however, he did not take a single trajectory route. He exercised a growth mindset and willingness to step sideways into unfamiliar territory. If you have a single track pathway in mind, you’re likely to miss incredible opportunities which will truly exercise your potential. Missing those opportunities is not something you want to regret.

2. Reverse plan your career pathway and set activity goals well in advance.

Author Marshall Goldsmith’s words: “What got you here won’t get you there” have scientific research to warrant them true. Researchers Jooyoung Park, Lu Fang-Chi and William Hedgcock found reverse (backward) planning not only led to greater motivation, higher goal expectancy, and less time pressure but also resulted in better goal-relevant performance. Start with the end in mind, work backward and you’re more likely to have successful, validating work experiences. When you can map your pathway using this method, you’re unlikely to make career decisions you’ll regret.

Also set yourself challenges to practice improving both technical and personal skills, even within the first ninety days. Expanding your individual capabilities will increase your mental and emotional familiarity toward becoming what you need to be to achieve the goals you set. Build structured learning into your experiential activity goals.

Don’t be the perpetual course junkie or an avid reader who loves to learn but achieves no desired changes. Devise two lessons and plant activities against them that will shift you from your current position and take you further toward your goals. Work with a coach and come clean with what you experienced, achieved or did not achieve. Acknowledge what both scared you and excited you.

Monitoring your progress from a holistic perspective will make it very hard for you to regret taking action. Career decisions that contain well-planned and calculated activities rarely hold regret.

3. Never make decisions in an unbalanced mood state.

Research shows exercising emotional intelligence to restore oneself to a balanced, positive mood state reduces the likelihood of making regretful career-decisions. Therefore, ensure you never make career decisions — or any important decisions — in a negative emotional state or a euphoric one.

Negative moods go hand in hand with fixed mindsets. You have limited capacity to see bad decisions you have made from any other perspective and have a lower ability to think of ideas and actions to reverse them if you feel you’ve indeed made a grave mistake. Conversely, making decisions in a twister-like state of euphoria is also dangerous. You can miss fine details which could cost you dearly. The next time you attend a high energy event promoting a ten thousand dollar digital marketing package which promises to boost your business, think again. Even better, leave your credit card at home.

This article is from Entrepreneur.com