How to make career decisions that you will not regret for life

How to make career decisions that you will not regret for life

What makes big decisions so hard? As a decision coach, I see many people struggle with tough choices, because they really, really want to have no regrets.

While I’ve never met anyone who felt they got it right 100% of the time, going back to the basics can help you get clear on what you want and feel better about moving forward.

Here are five simple strategies I’ve learned for lessening the odds that you’ll look back and wish you did it differently.

1. You’ve Got to Collect All the Information

The first step is research. If you make a decision without the proper information—like joining a company without learning what the culture is really like—you’re setting yourself up for disappointment later on when you learn something that would’ve made a difference.

Putting the time in on the front end means fewer chances for regret down the line. You don’t want to be thinking, “If only I’d checked out the website more closely!” or “I should’ve asked that in my interview!” You want to be thinking, “I did my research and made the best decision I could.”

2. You’ve Got to Chill Out

Making a choice is stressful by nature, but doing it from a place of calm consideration lowers your chance of making the wrong one. That’s because the calmer you are, the less likely you are to make a hasty, emotional decision.

Try to get into a relaxed state of mind, remove any stressors—including people—from the room, and think through your decision with a clear head and an open mind. Don’t rush, don’t freak out; instead, take deep breaths and think about the facts.

If you’re not in the right state, ask yourself if you have to weigh your options right then, or if you can wait until a better time (i.e., “sleeping on it” usually helps).

3. You’ve Got to Know All the Options

A client recently asked me to help her think through a big, cross-country move. Her husband had a job offer with a higher salary in the new location; and while they loved where they were, they were struggling financially in an expensive city.

I pointed out that her options weren’t simply to take the job or to stay and continue to barely make ends meet. There were other ways she could change her situation: her husband could ask for a raise, she could look for part-time work, or they could downsize their house. Don’t leave any option unexplored, no matter how unlikely it seems: You want to know the full range of choices and not limit yourself to two.

4. You’ve Got to Keep a List

Instead of just going through the pros and cons in your head, write them out in list form. It’s not just a matter of clarifying important points and picking a side. Keeping the list will help you minimize regret, because if you start to second-guess yourself later on, you’ll have evidence for why you made the decision you did.

Sometimes, a simple reminder that your choice was based on concrete factors and the best information you had at the time—and wasn’t just made on a whim—can help re-configure your thinking so you feel better about the path you took.

5. You’ve Got to Keep Things in Perspective

This is important both during decision-making and afterwards. We often get so caught up in finding the best option that it consumes us. Reminding yourself that things are going to be OK no matter which choice you make—which is true most of the time—puts you in the right mindset for a regret-free decision.

You’re not perfect—and that’s OK, no one is. Sometimes, we choose badly, or circumstances beyond our control mean that a decision we made wasn’t the right one. Regret is usually unproductive and pointless, and although that doesn’t help when you feel like you made a huge mistake, the less time you spend dwelling on what could have been, the better.

If all else fails, try to channel that regret into something useful. Making a poor decision prepares you for better decision making in the future. Analyze what went wrong, refine your process, and move forward.

How to make career decisions that you will not regret for life

How to make career decisions that you will not regret for life

Success is all about costs and benefits.

Photo Credit: @eyeforebony

Many of the wisest people in the world have given up on the idea that there are “winners” and “losers” in life. While it might seem that your boss has it made with a higher salary and status, that comes at the cost of long hours, stress, and not being able to spend time with family. At the other end of the spectrum, the person serving food at a fast-food restaurant might seem like they have a long way to go. But their low levels of stress and passion for things besides their work could mean that they have a great life.

Success, therefore, is all about costs and benefits. While going for a better job will net you more income, it could also bring a host of new problems your way.

A lot of career-minded people will set out to progress no matter what. But as they do so, they discover that they have regrets. They’re “winning” in their careers, but losing in life.

Making big career decisions without regrets is a challenge. Here are some insightful strategies that you can use to make sure that you don’t wind up making a massive mistake.

Think Carefully About Whether You Can Work Overseas

Working overseas is one of the most potent things that you can do to improve your career prospects. Employment in a new country can open up a whole host of opportunities.

Sorting out visas is your top priority. Results Migration has one of the highest success rates in helping foreign workers get the documentation that they need. But that’s just process-related stuff. What matters is how moving abroad makes you feel.

If you’re somebody looking for a brand new start in life, it could suit you perfectly. If, however, you’re a pillar of your local community, moving might not be an option right now. Plus, you have to think about your personal needs too. Can you deal with being far away from your friends and family? It is an important consideration.

Research, Research, Research!

Going for a new job can sometimes be a once in a lifetime opportunity. It is essential, therefore, that you capitalize on the situation. You don’t want to find yourself in a position where you could have got the job if you’d prepared better.

Researching as much as you can about a potential employer before you go to an interview, therefore, is vital. The more you know in advance, the more likely you are to get the job.

Research is essential for another reason: it helps you find out whether a particular employer is a good match. You don’t want to hop from a culture you love to the one that you despise. It could wreck your happiness.

Know Your Options

Finally, you must know your options. While taking a new position in a different company might seem like the only way to improve your financial situation, there are alternatives. Asking for a raise at your current place of work, for instance, is often worth a shot.

How to make career decisions that you will not regret for life

What makes big decisions so hard? As a decision coach, I see many people struggle with tough choices, because they really, really want to have no regrets.

While I’ve never met anyone who felt they got it right 100% of the time, going back to the basics can help you get clear on what you want and feel better about moving forward.

Here are five simple strategies I’ve learned for lessening the odds that you’ll look back and wish you did it differently.

1. You’ve Got to Collect All the Information

The first step is research. If you make a decision without the proper information—like joining a company without learning what the culture is really like—you’re setting yourself up for disappointment later on when you learn something that would’ve made a difference.

Putting the time in on the front end means fewer chances for regret down the line. You don’t want to be thinking, “If only I’d checked out the website more closely!” or “I should’ve asked that in my interview!” You want to be thinking, “I did my research and made the best decision I could.”

2. You’ve Got to Chill Out

Making a choice is stressful by nature, but doing it from a place of calm consideration lowers your chance of making the wrong one. That’s because the calmer you are, the less likely you are to make a hasty, emotional decision.

Try to get into a relaxed state of mind, remove any stressors—including people—from the room, and think through your decision with a clear head and an open mind. Don’t rush, don’t freak out; instead, take deep breaths and think about the facts.

If you’re not in the right state, ask yourself if you have to weigh your options right then, or if you can wait until a better time (i.e., “sleeping on it” usually helps).

3. You’ve Got to Know All the Options

A client recently asked me to help her think through a big, cross-country move. Her husband had a job offer with a higher salary in the new location; and while they loved where they were, they were struggling financially in an expensive city.

I pointed out that her options weren’t simply to take the job or to stay and continue to barely make ends meet. There were other ways she could change her situation: her husband could ask for a raise, she could look for part-time work, or they could downsize their house. Don’t leave any option unexplored, no matter how unlikely it seems: You want to know the full range of choices and not limit yourself to two.

4. You’ve Got to Keep a List

Instead of just going through the pros and cons in your head, write them out in list form. It’s not just a matter of clarifying important points and picking a side. Keeping the list will help you minimize regret, because if you start to second-guess yourself later on, you’ll have evidence for why you made the decision you did.

Sometimes, a simple reminder that your choice was based on concrete factors and the best information you had at the time—and wasn’t just made on a whim—can help re-configure your thinking so you feel better about the path you took.

5. You’ve Got to Keep Things in Perspective

This is important both during decision-making and afterwards. We often get so caught up in finding the best option that it consumes us. Reminding yourself that things are going to be OK no matter which choice you make—which is true most of the time—puts you in the right mindset for a regret-free decision.

You’re not perfect—and that’s OK, no one is. Sometimes, we choose badly, or circumstances beyond our control mean that a decision we made wasn’t the right one. Regret is usually unproductive and pointless, and although that doesn’t help when you feel like you made a huge mistake, the less time you spend dwelling on what could have been, the better.

If all else fails, try to channel that regret into something useful. Making a poor decision prepares you for better decision making in the future. Analyze what went wrong, refine your process, and move forward.

Looking in the rear-view mirror can cause an accident!

How to make career decisions that you will not regret for life

Regret. It seems to be a fact of life: the one who got away, the job you didn’t take, the fight you wish you hadn’t had, the choice of the wrong school, the investment you didn’t make, the money you didn’t save, the move you wish you’d made, and on and on and on.

That’s the predictability of life; there will definitely be something along the way you will wish you’d done differently. Regrets can be big — choosing the wrong career — or small — picking a dress you really don’t feel good in for the senior prom. They can occur daily, or you can have overarching ones that just seem to color everything you do.

There are a number of cognitive reasons why regret is a factor for most of us. To read more on the literature behind this, visit the National Institutes of Health website on the subject.

Regret on its own is not a bad thing; in fact, it can spur us to action. The parent who has been working too much and might be preoccupied around the children might happen to see an ad, or a parent playing in a carefree manner at the playground with their similar-aged child. This parent might feel a twinge of regret for not focusing on their own child more and may then actually spend more time with their child. People who get terminal diagnoses may regret time wasted and realize that every second is precious, and resolve to enjoy each and every moment they have left. Tim McGraw’s song, “Live Like You Were Dyin’,” sums this experience up well. Someone who regrets choosing a particular career path may find themselves approaching retirement and resolve to quit and pursue the career of their dreams. The examples of people who turned something around, tried something new, or charted a new course because regret motivated them are endless.

But for some people, regret becomes something more like an albatross. Too many regrets can sometimes materialize into an overall feeling of being wrong or bad: “I never seem to make the right decisions” or “I always choose the wrong thing for me.” Or regret may cause paralysis because you mourn what you could have or should have done, and can’t seem to make a better decision going forward. This becomes like driving down the highway, constantly looking in the rear-view mirror at what you have left behind. Not only do you not enjoy the scenery as you pass it, but it’s dangerous to drive without looking ahead and being present to what’s beside and in front of you.

If regret has become debilitating for you and is not spurring you to improve, but rather feels like the small mirror you are constantly checking behind you, maybe it’s time to let go of the regrettable experiences and move on to something new. While you can learn from any mistake, the only thing any human being has to work with is their present, and hopefully future, state. The present is where the action really is, and being present to where you are now and resolving to make better decisions going forward should be your commitment. But if you have become locked on the rear-view mirror, how do you tear your attention away? After all, you might be looking at something pretty appealing back there that you left behind or choose to ignore!

Consider these steps to stop looking back and start being present to your present, and working on your future:

  1. Own it. Yes, whatever it is that happened, happened. You made the wrong choice, said the wrong thing, went in the wrong direction. Whatever it is, it’s done. And you know what? It’s over. The fact of the human condition is that you won’t always choose wisely, and you won’t choose in your best interests every time. Sometimes you don’t have the right information. Sometimes emotions overrule your thinking, sometimes thinking overrules your “gut.” You might not have enough time to consider options, or you might have pressure on you to choose a way. Whatever it is, the bottom line is that the conditions are not always optimal for anyone to make the perfect decision every time. Give yourself a break. Own it, and love yourself anyway. It’s done and you can’t go back in history and rewrite. Cry. Mourn. Scream. Pound the pillows. Do whatever you need to (without harming yourself or others) to get the emotion out, then let it go.
  2. Learn from it. Try and take an objective view of what happened. Why did you do/decide what you did? This is not an opportunity to bash yourself, but rather to examine the event critically. You can learn a lot about how you make decisions by trying to understand what went awry. Do you need to do a better job next time of gathering information? Do you need more time to think something through? Are you unduly influenced by others? Note what you need to do differently the next time you have a decision to make.
  3. Write out what you would like. If you regret a lost (or found) relationship, a career choice, a financial decision, an educational experience, then instead of focusing on “what if I had,” focus on “what I want.” You can’t revisit the past, but you can turn your attention to something you want. So this career isn’t the best one; how do you paint a picture of something you do want? So the person you let get away got away; how do you create a life you can enjoy as a single person? So you didn’t go to the school of your dreams; how can you structure a plan to take classes or become involved at the school you did go to? Paint a picture in as much detail as you can about where you’d like to head. This will start turning your attention away from the rear-view mirror and to the windshield looking forward.
  4. Become entranced by today. Turn your attention to senses. Smell, taste, hear, and enjoy whatever it is you are doing at a greater level than you have done before. Really engage with your world. Notice things you haven’t noticed before, and resolve to be PRESENT with whatever is going on. As Oprah Winfrey said, “Whatever has happened to you in your past has no power over this present moment, because life is now.” Get involved with the now and heighten your senses to what’s around you. The mind can’t focus on two things at once, so if you turn your attention to your surroundings, you won’t be able to focus on your rear-view regrets.
  5. Make a plan for something you can do that might help to cancel out what you regret. For example, you didn’t spend enough time with your kids growing up and now they won’t visit you much? How about volunteering at an orphanage or joining an organization like Big Brothers Big Sisters? Missed out on the career you always wanted? What about taking up some hobby you are passionate about and pursuing that instead? Life is not linear, nor is it black and white. What shades of grey could you incorporate into your life that wouldn’t necessarily change the regret, but might add something important to the life you are leading today?

If you keep driving with your eyes on what you’ve left behind, you are bound to eventually crash. Take the steps to get your eyes back on the road and see the scenery of today, and focus on where you are going.

How to make career decisions that you will not regret for life

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Most of the choices we make every day are simple and straight-forward: what to wear to work, what to eat for lunch, whether to go to sleep at a reasonable hour or stay up watching Netflix. They don’t cause much stress or inner conflict.

Career transition points, on the other hand, can leave you feeling significantly more stuck—especially when you’re facing a big, life-changing decisions.

Should you take that promotion? Move to a different city? Transition to a new industry? Launch a business or take your side hustle full-time?

Decision-making is tough, particularly when there may not be one “right” answer. Despite your best efforts, it’s not always clear what to do next. How do you know whether you’re heading in the right direction, or about to make a bad career move you’ll regret?

1. You have a sense of foreboding.

Just about everyone has experienced a feeling that something is “off” or a sense of dread they can’t shake. Does that sensation creep up when you think about the new opportunity?

(Photo courtesy of Shutterstock)

Maybe you didn’t feel much of a connection with the new team you’d potentially be working with when you met them. Or perhaps you’re starting to worry about relocation costs and not as willing to take a pay cut as you first thought.

Although most of us come equipped with a sense of intuition when something doesn’t feel right, we also have plenty of ways to rationalize these feelings away and ultimately discount them. You certainly don’t want to turn down a great offer or miss out on a solid opportunity because you’re feeling nervous. A big career move is bound to cause some butterflies.

But an ongoing feeling of discomfort could be a sign you’re not ready or that this career move isn’t the best option for you. Try out the 10/10/10 test to slow down your thinking and separate fact from fiction in your mind: will this concern matter 10 weeks from now? 10 months from now? 10 years? Your answers can help you put things in perspective.

For instance, if you’re incompatible with your colleagues, that could absolutely matter 10 months or even 10 years down the line. Getting used to a longer commute, however, might be something you could become accustomed to in 10 weeks or less.

2. You’re feeling desperate.

Feelings of desperation may take root when you’re deeply unhappy with your current position, or when you and your family are in a difficult financial situation. You might have an anxious feeling of simply wanting to get the decision over with.

When you feel panicky, it’s tough to maintain perspective, so consult someone who doesn’t share your emotional attachment to the situation. This may include a trusted friend, mentor or coach who can help you sort through options in an objective way. You may be amazed at how much easier it is to calm down and think rationally after getting out of your own head.

3. Your motivations aren’t healthy.

Be honest with yourself: are you considering this opportunity to spite someone else—to make your old co-workers jealous maybe? Taking a new job to sidestep criticism from family and friends or hiding the decision altogether are also bad signs you’re making an escape-based choice that you could regret in the future.

Gallery: 10 Things To Do When You Hate Your Job

If you find yourself venting to anyone who will listen ranging from your mom to a stranger on the bus or indiscriminately seeking advice, you’re likely being driven by fear. This type of “polling” behavior is done in an attempt to feel better. You seek external validation that you’re doing the right thing. But you essentially outsource your decision making to other people when you ask everyone for advice instead of becoming self-reliant. It’s important to learn to trust yourself.

4. You have to talk yourself into it.

You may find the pep talks you give yourself turning into last-resort trumpet songs. Your self-talk may include some version of the phrase, “Well, at least I…”

  • “Well, at least I have a job…”
  • “Well, at least I’ll be making more money…”
  • “Well, at least it will technically be a promotion…”
  • “Well, at least I won’t look stupid for passing off this opportunity…”

This type of anxious internal dialogue, called intellectualization, is a common response to anxiety. Because strong emotions can be uncomfortable, we overly focus on facts and logic.

While being rational and using reason can of course be a great thing, it can also signal denial. Deep down, you know your possible career choice might be a bad idea. This isn’t a productive frame of mind for making decisions about a career move because you’re talking yourself into something you don’t truly believe is right for you.

5. You’re restless.

The complicated nature of a significant career decision might make you feel completely preoccupied or keep you up at night tossing and turning. Any career transition can send you for a loop, but you should be able to see promise in what you’ll be able to learn through the process. Whether it’s taking on a promotion or starting a company, you might feel far outside your comfort zone, but you’ll also feel excited about everything you’ll learn.

With big decisions come uncertainty. Learning to balance your head and heart is an ongoing process . Take the false pressure off of yourself to know all the right answers, right now. No matter what you choose, move forward with confidence, knowing that your career is always evolving.

The next positive change might be right around the corner.

If you’re questioning your job right now, here are some actionable steps you can take.

No matter how old we are or how long we’ve been working, we all have questions when it comes to careers—from how to respond to a rejection letter to learning to say no when a role isn’t a good fit. That’s where Career Counselor comes in. In this weekly series, we connect with experts to answer all of your work-related questions. Because while we don’t all have the luxury of a career coach, we still deserve to grow in our careers.

I wish I had picked a different job. I wish I had asked for more money. I wish I had taken more chances. I wish I had focused more. I wish I had asked for a mentor. I wish I had quit that job sooner. I just wish I had done things… differently.

If any of this sounds familiar, know you’re not alone. While career regrets are incredibly common, the onslaught of coronavirus (COVID-19) layoffs has made folks even more likely to beat themselves up for not doing things differently when it comes to their professions. According to Forbes, a new study from the journal Emotion shows that humans are most inclined to regret things associated with opportunities. The greater we regard the opportunity, the more likely we are to experience regret. And since many of us have experienced dramatic career shifts in the last few weeks, it’s easy to ruminate and create fantasies about what we “should” have done in order to have more opportunities in this trying time—even when something is totally out of our control.

If this resonates, take a deep breath. None of us could have prepared for a national pandemic, and you likely were doing the best you could when you made the decisions that you did. (Even Michelin-star chefs are unemployed right now!) Now that you’ve forgiven your past self, let’s turn to the future. Because here’s the good news: Many of our so-called “mistakes” don’t need to become regrets. In fact, those mistakes can actually lead to valuable insights on our desires and ambitions.

We spoke to career strategist and leadership coach Emily Eliza Moyer about career regrets, why we have them, and what we can learn from them—even in the time of COVID-19.

HelloGiggles (HG): What would you say are the most common career regrets you’ve witnessed?

Emily Eliza Moyer (EEM): The most common career regrets include wishing you had followed a career dream earlier in life, choosing the wrong career path, not being authentic at work, or feeling like you generally made the wrong decision about something.

HG: What are some reasons one might experience professional regrets?

(EEM): Most people’s reasons for experiencing professional regrets are making decisions based on gaining someone else’s approval, not listening or trusting your own intuition, or taking on personal responsibility for someone else’s emotions.

HG: We live in a world that leaves a lot of room for comparison. I think it can be hard for folks to see their friends doing XYZ, compare, and worry that they “did things wrong.” What would you advise someone with this mindset?

(EEM): The common assumption is that comparison is the thief of all joy. I certainly believe this, but it’s only natural as humans for us to observe each others’ lives and compare them to our own. The problem arises when you live in the space of focusing on what someone else has that you don’t have.

When jealousy arises, or when you see someone who has something else that you want and it makes you feel something negative, bring awareness to those thoughts. Notice if you’re dwelling in the negative emotions associated with comparison. Instead, choose to see comparison differently. Allow yourself to step out of the negative emotions and ask: Is what they have really something that I want? If the answer is a resounding yes, then ask: what would I need to do to achieve that? What mindsets might I need to shift? What decisions might I need to make differently? Let comparison, instead, be an expansion of what’s possible for you too.

HG: I also think people can easily slide into “it’s too late” thinking because they didn’t do XYZ in their undergrad, twenties, and beyond. Is it ever “too late” and if not, how can we challenge this attitude?

(EEM): It is absolutely never too late to make a change in our lives. As humans, we’re wired to continuously grow, learn and evolve. We’re never starting over because even if you are transitioning into something new and you’re a beginner, you’re carrying all of your previous skills, experience, and knowledge with you. In every industry, we can see examples of people who became successful much later in life. It’s a societal assumption that it’s “harder” to pivot after a certain age. But, who says that’s true? Consider this: The older you are, the more experience you have and the more connections you can lean on. You know how you learn, you’re less afraid of failure, you care less about what others think and you know what’s right for you. Could it be possible that following dreams later in life is actually much easier and could even mean you’re much more likely to succeed?

HG: Is there a positive way that we can look at career regrets? What can we learn from them?

(EEM): Regrets are the feeling of looking back on decisions that you made and wishing you’d done something different. The feeling of regret is just that—a feeling. Feelings are information; they tell us stuff. They point out something that needs to be processed or something that needs to be looked at more deeply. Regrets are signals; they’re your intuition speaking to you, telling you that you have an option to do something different. Regret in itself can be the opportunity to make a new choice. Many times people interpret regret as a permanent state, a given that will just live with you. But feelings are by nature, fleeting. Let the temporary feeling of regret be an opportunity to tune into yourself and ask, what do I really want?

Like everything in life, every mistake, every challenge, every regret is an opportunity to learn.

HG: What actionable steps would you give to someone in order to move past their regrets?

(EEM): Bring awareness to your feeling of regret. When does it come up for you? What does it feel like in your body? What other emotions is it associated with? Then, carve out some time for yourself to journal on this feeling. What is it bringing up for you? Why are these regrets? What is the feeling actually trying to tell me?

You might find that your feeling of regret appears when you’re comparing yourself to someone else, but with further investigation, you don’t actually want what they have. Maybe you made a tough career decision and your feeling of regret is a signal that you still haven’t forgiven yourself for it. Or possibly, your regret is showing you that someone else followed their dream, and now it’s actually time for you to go follow yours.

Last Updated: April 7, 2021 References

This article was co-authored by Guy Reichard. Guy Reichard is an Executive Life Coach and the Founder of HeartRich Coaching & Training, a professional life coaching and inner leadership training provider based in Toronto, Ontario, Canada. He works with people to create more meaning, purpose, well-being, and fulfillment in their lives. Guy has over 10 years of personal growth coaching and resilience training experience, helping clients enhance and transform their inner worlds, so they can be a more positive and powerful influence on those they love and lead. He is an Adler Certified Professional Coach (ACPC), and is accredited by the International Coach Federation. He earned a BA in Psychology from York University in 1997 and a Master of Business Administration (MBA) from York University in 2000.

There are 12 references cited in this article, which can be found at the bottom of the page.

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Making a choice between two or more options can be a difficult and overwhelming experience. Especially if the decision will affect you in the long-term, you may wonder if you will make the right choice. And even smaller choices may leave you feeling anxious and doubtful. But you can make choices without regret if you evaluate your options and make your decision. Then, build confidence in yourself and accept the consequences of your choices.

How to make career decisions that you will not regret for life

Guy Reichard
Executive Life Coach Expert Interview. 19 March 2020.

  • Think back to the times when you felt happiest. What were you doing? Who were you with (or were you alone)? What made you feel happy in that moment?
  • Think about when you felt proud of yourself. Why were you proud? Did other people share in those feelings of pride? Who?
  • Think about times you felt satisfied, content, and fulfilled. What need or desire was fulfilled? How and why did the experience give your life meaning? What were some of the other factors at play that gave you this feeling of satisfaction?
  • Using the information you have gathered, identify commonalities (Were you always with a family member? Was your passion for singing always a factor?). Then try to identify 10 values and rank them from most important to least.
  • Values may include faith, family, adventurousness, empathy, generosity, service, nature, achievement, and more.
  • Once you have identified your values, ask yourself if your decisions align with your values. Would taking a new job in a foreign country violate your top value of spending time with family? Would skipping class support or violate your top values of accountability and achievement?

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What makes a good decision? When I ask people that question, I often get answers like:

“When the outcome is successful.”

Why is it that we, as a society, romanticize outcomes? Only things and people that succeed are celebrated. Just look at all the articles and books that idolize successful people. And to a degree, that’s obvious.

But it’s also misleading. We tend to overlook cases that did not come with a successful outcome. And when we do look at failure, we are often quick to explain why things failed.

How to make career decisions that you will not regret for life

In hindsight, we can all look at mistakes and say that it was imminent. But if preventing mistakes is that easy, why are we still make decisions that we regret?

Take the case of the Titanic. Looking back, we all know that the luxury liner that traveled from Southampton to New York made many costly mistakes.

For example, it is well known that the Titanic didn’t carry enough lifeboats.

“What happens when all the lifeboats are used in case of an emergency?” is something that someone surely said, right? We just don’t know! We weren’t there.

How about another interesting fact? The Titanic was tested for 6 hours and never with a full crew. After that, they loaded up the passengers and set sail towards New York.

“Shouldn’t we try this thing out more before we bring passengers on board?” someone surely said. I guess not.

But here’s the thing. No one wanted the Titanic disaster to happen. And no one predicted it … Until after the fact.

A few decades before all those innocent people died, Fyodor Dostoevsky famously said:

“Everything seems stupid when it fails.”

Bad decisions and good decisions

It’s easy to look at success and attribute it to good decision making. But here’s the thing—that statement is also true the other way around.

Failure is not always explained by bad decision making. However, that’s what most historians do. But like Dostoevsky said, in hindsight failure is always obvious.

The people who were responsible for the Titanic probably thought they were making the right decisions at the time. After the fact, they probably regretted many things.

But I don’t think good or bad decisions have anything to do with the outcome. Peter Bevelin, the author of Seeking Wisdom, puts it well:

“Good decisions can lead to bad outcomes and vice versa.”

The truth is: You can’t predict the future. Sometimes even bad decisions can lead to good outcomes.

So that’s why I think it’s pointless when people pretend they can teach you how to make “good” decisions. There’s no such thing. Any person who’s failed a lot in life will tell you that.

Mental models: Focus on the process, not the outcome

The way you look at how something works in the real world is called a mental model. It’s your thinking framework about something.

But when we make decisions, we often don’t think about our framework and immediately jump to a discussion about potential outcomes.

We ask, “What will happen if we make this decision?”

That’s an incomprehensive method because you’re not questioning your decision-making process. You’re only looking at the outcome.

But have you considered what specific thinking frameworks (mental models) you can use for your decision?

Too often, we skip the process and jump right to deciding. Maybe that’s due to a lack of time, resources, or knowledge — it doesn’t matter.

Whatever your reason is, it’s never an excuse to skip the decision-making process altogether. Because that’s the only way to become a bad decision maker — regardless of the outcome.

So instead of focusing on how successful your choices are, focus on how comprehensive your decision-making process is.

Look, you don’t have to know everything about mental models — I certainly don’t. Most pseudo-intellectuals spend more time talking about what a mental model is instead of using them to achieve anything meaningful in life. They just like to define mental models.

But as you and I both know, knowledge without application is useless.

That’s why I recommend reading only the following 3 books that focus on this topic:

    Seeking Wisdom by Peter Bevelin — Discusses the mental models of Charlie Munger and Warren Buffett.

We can never predict the future, nor can we know all mental models that exist. But we can make decisions we don’t regret.

By simply focusing on the thinking process, we can always say we did the right thing. And that’s the only sure way to avoid regret—no matter what the outcome is.

“What’s the right thing?”

It’s clear we should never regret making mistakes. Every mistake is a lesson after all. However, there’s another type of regret that literally kills people. It’s the regret of inaction.

I’ve seen this up close with my grandmother. At the end of her life, she drowned in her own sorrow. And that sorrow was solely made up from regret about the things she never did.

Look, no matter what you do, we all suffer in life. But there’s a difference in suffering, as Jim Rohn once said:

“We must all suffer one of two things: the pain of discipline or the pain of regret or disappointment.”

Achieving your goals. Improving yourself and your relationships. Writing a book. Building a business. It’s painful. It takes a lot of time, energy, and sacrifice to achieve things that are worthwhile in life.

But you know what’s also painful? The regret of inaction, disappointment, and laziness.

Which type of suffering hurts more? It’s up to you to decide.

Thanks for reading!

I also wrote a book on this topic. It’s called THINK STRAIGHT. Check it out if you want to learn more about controlling your thoughts.

Last Updated: April 7, 2021 References

This article was co-authored by Guy Reichard. Guy Reichard is an Executive Life Coach and the Founder of HeartRich Coaching & Training, a professional life coaching and inner leadership training provider based in Toronto, Ontario, Canada. He works with people to create more meaning, purpose, well-being, and fulfillment in their lives. Guy has over 10 years of personal growth coaching and resilience training experience, helping clients enhance and transform their inner worlds, so they can be a more positive and powerful influence on those they love and lead. He is an Adler Certified Professional Coach (ACPC), and is accredited by the International Coach Federation. He earned a BA in Psychology from York University in 1997 and a Master of Business Administration (MBA) from York University in 2000.

There are 12 references cited in this article, which can be found at the bottom of the page.

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Making a choice between two or more options can be a difficult and overwhelming experience. Especially if the decision will affect you in the long-term, you may wonder if you will make the right choice. And even smaller choices may leave you feeling anxious and doubtful. But you can make choices without regret if you evaluate your options and make your decision. Then, build confidence in yourself and accept the consequences of your choices.

How to make career decisions that you will not regret for life

Guy Reichard
Executive Life Coach Expert Interview. 19 March 2020.

  • Think back to the times when you felt happiest. What were you doing? Who were you with (or were you alone)? What made you feel happy in that moment?
  • Think about when you felt proud of yourself. Why were you proud? Did other people share in those feelings of pride? Who?
  • Think about times you felt satisfied, content, and fulfilled. What need or desire was fulfilled? How and why did the experience give your life meaning? What were some of the other factors at play that gave you this feeling of satisfaction?
  • Using the information you have gathered, identify commonalities (Were you always with a family member? Was your passion for singing always a factor?). Then try to identify 10 values and rank them from most important to least.
  • Values may include faith, family, adventurousness, empathy, generosity, service, nature, achievement, and more.
  • Once you have identified your values, ask yourself if your decisions align with your values. Would taking a new job in a foreign country violate your top value of spending time with family? Would skipping class support or violate your top values of accountability and achievement?