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6 Career Regrets You'll Have at 40 (But You Should Be Thankful For)

Not all career decisions end up being amusing stories we can tell later even if things turned out OK. We often lack foresight and insight when we’re in our early 20s. There are times our "yes" should have been "no"—and vice versa.


Setting career strategies and goals are not easy. Yes, we want to take control of our career by accepting full responsibility for our actions, creating opportunities for ourselves, and staying connected. There are those times when we put lots of food on our plate, but we won't eat it all, and often waste the food.


Some decisions seem horrible at the time, but it was the right call. Those are the ones you may not appreciate until later, like when you're over 40. I thought of a few, and perhaps you can spot them sooner than I did:

1. You said "no" and missed out

When you're young, you value moving up the ladder and want the life experiences with friends. You want both, but the time you said "no" to career opportunities (or a single one) leaves you with feelings  of unrequited love. On the trip back to reality your values mean more than status, and contentment means more than confinement in a career.


It's bittersweet but those relationships you built through your experiences were too valuable. Now you understand these relationships start the process way before any crisis. You gain intelligence from coffee conversations, networking events, and a few informational interviews. Only after a few interactions your resume will take a relevant shape.


2. You were fired and afterward, your career stalled

How does it feel when you realized being "fired" was either a great new beginning or a shareable life lesson? Being "let go" was not judgment day but it felt like it. If feels as if Satan in the form of disappointment is stalking you. It took years to get over the sting. The needles and pins of pain. The cloudy and stormy feelings of shame.


Some people need help in understanding why it happened, but others discover freedom and relief quickly is what was supposed to happen. Counseling is not a bad thing, but neither is time. You lost a job for reasons not uncommon to man. If you haven't already reframed it positively in your mind, now is the time to do so for the rest of your career.


3. You chose life over money

We were told to have fun and work very hard in our 20s. Some of us were underemployed but refused to go home because we loved our freedom. We ate Spam or Ramen noodles to survive because we decided to immerse ourselves in our lives. The sting remained for years, but we can go to that place when challenges cloud our vision.

Sometimes we gain wisdom from there, other times clarity, or novocaine. You can see the ending to your story clearer, so now you save. Even better, happiness doesn't have the cash value it used to. Your ability to career management brings a smile and not a competitive smirk.


4. You lost track of tech and professional relationships

Certain technologies can become old-school in a short period of time.  You career path can become irrelevant as quick if you are not on top of trends in your industry. Your friends indirectly challenged you to keep up because they were moving and you knew you had to keep up.

Somewhere along the way relationships changed, priorities rearranged, and we feel we should start over again. Tech is infused with life now, so you have to catch up. It won't take long if you work at it daily.


5. You couldn't accept "no" from a potential employer

Rejection makes us a stronger, and boy is it painful at the time.  You spent more time over "what could have been" and less on the what you have. Sometimes it turned out great, and then you're grateful for the "trail."

Remember those who benefited from your path and the way it turned out because without you, and they are not better. Whether you just started a new job yesterday or 20 years ago, you can list 20 ways you're valuable to your next employer. And do yourself a favor: Keep adding to the list.


6. The bad boss had value after all

We may not like the messenger and hate the way the message was delivered, but the message was on point. Sometimes our jagged little life-saving pill was brought by an ugly carrier pigeon, and we reject the message for the wrong reasons. In our late 30s or early 40s, we realize when a more acceptable package our ugly acting boss was right. We hated how the message was delivered.

Don't worry, most of us have been there, but it would have saved us or someone else much heartache if we looked much deeper at the message. The diamond isn't in the delivery, but in the package.

We get to a place where we realize what's most useful, and valuable lessons are not the most recognizable at first. We may have gotten to a clearer space before 40. But the one thing we do know is upon arrival, and we appreciate the journey of our career more because the clarity is an irreplaceable part of our experience.

Last Updated: November 1, 2016
About the author

Mark Anthony Dyson

Mark Anthony Dyson is a career consultant, job seeker advocate, career writer, and founder of The Voice of Job Seekers. He helps the employed, unemployed, underemployed, and under-appreciated find jobs. Mark has published more than 400 articles on his blog as well as some of the largest career sites such as Recruiter.com, YouTern, and Come Recommended.