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What Has Been Your Biggest Career Mistake Example Answer

My biggest career mistake was never jumping ship to another employer. As a headhunter, I constantly warn candidates against the perils and drawbacks of taking a counteroffer. Alas when the shoe was on the other foot, I violated my own advice to my candidates: I took a counteroffer instead of moving with another firm to start a division in a different state.biggest career mistake example answer

Although I ended up retiring from my 9–5 anyways at age 28, I still harbor a regret for never having taken the plunge to work for another employer. I always wonder what my life would be like had I moved to another city to run my own headhunting team. It would have been fun to experience corporate life with another company.

what is the biggest mistake you’ve made in your career

Here are a few of the excuses I created for myself at the time of taking the counter-offer. Hopefully, you will take them into consideration to avoid a similar regret:

#1. Naivety. 

My employer groomed me from a young 23 year old with no experience to someone making over $200k at age 25. I felt so much loyalty, gratitude, and trust that I blindly believed that all their promises on “future equity and ownership”, higher position, and management changes would actually come to fruition. Alas, all went back to normal pretty quickly.

What I did not realize is this: at any employer, you are as good as your ability to earn money from your employers. They did not want to lose me bc of them would also be lost in my gaining capabilities for the company. At the end of the day, they do not have the same investment in my personal future as I did. They will seek the interest of the firm, not mine.

Now, I do not blame you for that because it is the scope of any contractual agreement between the employer and the employee. No firm owes you care, love, and true support. If you find one that does, it is very rare and good for you!

Most companies are run by people who are driven by selfishness, personal gain, and business pursuit of profits, you can not even blame them! That is the basis of capitalism, a system in which we operate and live, for better or worse. People have a family to support, things to do, a lot of stress on their plate. I can not reject another person’s dreams just because they did not take care of mine.

Lesson learned: It’s not your employer’s responsibility to take care of you. It’s your OWN responsibility to maneuver yourself into the best situation, personal and professional, you can get. Forget promises! Get it in writing, don’t settle. Don’t be afraid to look out for your best interests because at the end of the day, you don’t owe them anything either because you already earned your keep by doing a great job! Above all, don’t take anything personally.

#2. Romantic relationships are dangerous. 

I decided to take a counter partly based on geographic constraint self-imposed by my desire to date a guy I really liked at the time. The new job would take me away from this budding romance I had invested merely one month into. I thought that taking the counter offer will allow me to salvage and grow my relationship.

I was floored. Heartbroken, hysterical, dazed. His reasoning was simply that this whole job hullabaloo made him feel that I was putting too much pressure on making our relationship work.

Lesson learned: Don’t let any boyfriend/girlfriend, especially early on in a relationship, influence your decisions for yourself, financially, career-wise, or location-wise. Especially before you know if their intentions are sincere or just for the time being. I didn’t think it would happen to me, and yet it did! I ignored the red flags and pushed through with foolish ignorance; I suffered the consequences of the easy way out.


#3. Don’t make excuses. 

I just purchased my first condo in Brooklyn right at the time I was negotiating this new job deal. Partly because I wanted to stay in NY to be with my boyfriend at the time, I used the condo purchase to rationalize my emotion-driven decision to remain with my existing employer.

In order to rationalize my emotional decision, I made excuses that it will somehow be hard to manage as an absentee landlord. Even though I could have rented it out easily, I needed my excuses to justify my inability to commit to a big career move.

#4. Corporate cultures change.

Under my first manager and in the beginning of my employment, things were too perfect. I thought I’d be a lifer! In the 3rd year of my career, he suddenly decided to return to his home country for his future family plans. A new management philosophy, team, and dynamic was thrust upon me.

I found the new management style completely against how I like to operate. As a top performer, I’m used to special treatment, lots of autonomy, and blind trust in my capability to deliver. I have proved that since Day One. Instead, I was faced with limitations, pushback, and constraint on my ideas to drive my business forward. That, combined with some other elements eventually propelled me to want to leave.

Lesson learned: Things can happen any time, and you can’t control the outcome. Be ready at any time to act quickly should something happen to your career, culture, or current employer’s situation. It’s never too late to plan your next career move, no matter how happy you are. In fact, the happier you are, the more negotiation power and time you’ll have to explore new roles.

#5. Negotiate harder. 

As a headhunter who squeezed the best offers out of the toughest of employers for my candidates, you would think I would be great at negotiating for myself!

Due to my eagerness to leave my employer at the time, I didn’t negotiate as hard as I could have. Ironically, this made it easier to take the counteroffer. If I got an offer of double my base and a crazy guaranteed income, I would perhaps be more inclined to take the risk of jumping ship. The fact was, I clearly didn’t negotiate as hard as I should have to make sure I couldn’t back out.

Lesson learned: Hold yourself firm and fearless. Do not back down from the image you have for yourself. If you have the goods to back it up, go for it all the way. Don’t constrain yourself.

So what happened after?

Ultimately, I ended up staying at my firm for 2 more years. At that time, I built another division but I really lost my passion of being an employee. When I tried to jump back to the ship, I realized that I just did not want to be an employee any more.

Fortunately, I had taken advantage of my investment in Brooklyn, and also took another investment property a year earlier. It was time to retire. I gave up my resignation in the week immediately after my 5th anniversary with the signature and never looked back.

I would have loved to learn of another corporate culture, the environment and the management style. I hope my personal story resonates with some problems you may have experienced and others do not fall into a similar situation!

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