Don’t Make that Job Choice Mistake Again: Learning From Regret

mm Russ Finkelstein

There are certain phrases I hear, often, as a career coach, and this is one of them: “If I could go back and do it all over again…”

I hear it so often that I have to be careful not to overreact when I hear it. I have a very deep and soothing voice, but when I hear those words I want to make the high pitched squeal of an ambulance or fire truck, because you can’t do it all over again. You can’t.

I would hope that the sound emanating from me when those words are used would get across how upset I am for you, and for me. It really frustrates me.

To be fair, in the coaching work that I do with people, regret has value. It lets me know that someone has been processing or doing a ‘slow cooking’ treatment on an idea. It may just be tender enough, by the time the regret emerges, that we can take the idea out and pick it apart.

I heard someone say the fire alarm phrase the other day, again, and it had been a long day, and I realized I had to write this column rather than risk my vocal reputation as the James Earl Jones of the coaching world.

It turns out that regret in your career is a common place for most of us to visit. But trust me: It’s such a dangerous place to allow yourself to live. It is a place best for short and directed stays.

Regret usually surfaces during my coaching sessions in one of two ways. Either a person realizes they’ve been behaving a certain way for a long time, and that it’s held them back from moving forward in their life or career. Or there is one big regret—perhaps a decision to go to graduate school, or not to go to graduate school (you’d be surprised how many people seem to regret exactly the opposite things! Just as one person’s trash is another’s treasure, one person’s regret can often be another’s crowning achievement, professionally…). This big regret comes up almost every time the person is feeling an absence of clarity about what their next career move should be.

Next time you hear yourself say these words about work, I want you to imagine me as your off-screen, omnipotent narrator. I want to give you what the Japanese call a “satori”, or a sharp philosophical kick, a kind of spiritual awakening. Let’s use this as a teaching moment. Now, let me coach you through it…

There are two steps to learning from a regret. First, go back and examine the decision you took. Perhaps you decided to leave a job and move countries, in a rush, for some reason. Or, yes, maybe you decided not to go to graduate school. Or to pass up a job offer in favor of staying where you were for someone you thought you were in love with at that time, and he or she has since left you, God damn them all to Hell, or…to be nearer your family.

Step one: Ask yourself the following questions:

  • How you were feeling?
  • How did you make the decision?
  • Who did you engage in the process?

This is important. Before you can move through a regret, it’s important that you process why you’re feeling it, and, perhaps, decide to go a little easier on yourself for having made the decision in the circumstances. Remember my rule, if a friend shared with you the same information how would you react? You aren’t allowed to be less kind to them than you are to yourself.

Were you feeling particularly stressed out at the time? I knew a guy who left a start-up because he realized he had lost all confidence in  himself even though he was meeting with success, and another person who had recently gotten divorced in pretty fraught circumstances, before leaving a job he rather liked, most of the time. I had to coach these people to realize how much their state of mind was a factor in their decision-making. So it’s important to consider whether your decision-making process might have been affected by something unusual.

Next, reflect on what you could have known about your options. Most people draw conclusions in a premature way, and regret moving too quickly over a big decision. What do you wish you’d known before you made the choice you regret? What could you have known? Did you do the best you could to reach out and find out the answers you needed?

Remember whom you engaged in the process. Who did you rely on to help you make this choice? Were they helpful? Did they listen well or did they, too, approach your problem with an agenda? My suggestion is always to involve more, rather than fewer, people, in a major decision. It’s simply not a good idea to make any sudden moves without consulting a trusted network of supportive friends first.

Step two: Write down what you learned, and keep it somewhere for safekeeping. Google Drives are a good place to keep this kind of thing.

Step three: Recognize that a big choice is before you. Locate the saved set of material from Step two. And now, for this next big decision, answer:

  • What’s your emotional state?
  • What information do you have, and need?
  • Who is going to be your sounding board?
  • What are your key takeaways from your most recent decisions?

The next time you are faced with a big choice, the key thing is for you not to feel a deep sense of regret in the future. And it turns out, there’s a lot you can do to avoid it.

When it comes to how you’re feeling, it’s important to ask yourself how emotionally strong you are, right now. Do you need some rest, for example, before you take a major choice? Are you feeling burned out? Are financial considerations weighing heavily on your mind? Is there any way you can alleviate any of those factors before you make your decision? If not, that’s okay. But remember they’re a factor in your choice and you will want to share those, when you reach out to others.

Now, the facts: What do you need to know about the new opportunity, or the employer, in order to be successful there? How will you learn it?

Who is going to be your sounding board? Who do you know with the right standing to be your conversation partner before you make this choice? I’m going to be annoying here and tell you: Your partner and your parents aren’t always the best choices in this situation. It might need to be somebody with professional standing who is senior and more experienced than you are, in your field. Those who love you outside a professional context can be helpful, but you want to be sure that your partners in these conversations have a strategic mindset.

If you felt that you had wasted time or money on a decision around a car purchase or vacation, you would make a careful examination of where you want wrong, to ensure that the next big choice would learn and adapt from those mistakes. You would think about the awful friend or publication that recommended the beach or vehicle. You would try to recall what you thought you aspired to.

Your next big decision should not, and need not, be based on a completely blank state, but people do often forget and make a choice because they feel like the choosing is hard. Choosing can be hard, but living with a poorly made choice can feel impossible. Here’s to fewer regrets.

Russ Finkelstein is Managing Director of ClearlyNext, a guided online career program that helps people of all backgrounds and incomes figure out what to do next. Read more >