From Career Regret to Reinvention: How to Move Past Pain & Design Your Ideal Career

In 1995 there was a man living in Liverpool who played the same set of lottery numbers every week. One week, when he failed to renew his ticket, his numbers came in. His distress over losing what he thought was millions of dollars (a fact he actually ended up being wrong about), was so unbearable that he committed suicide.

That is real regret. The kind of regret that happens when we see the difference between how a situation is and how it could have been had we made a different choice.

Imagine if you were offered a trip back in time so you can undo your biggest regret. If you could live your life all over again, what’s the one thing you would do differently?

When I ask myself that question, the words shoot out of my mouth without even thinking: my educational and career choices.

It turns out I’m not alone. In the book If Only, author Neale J. Roese, Ph.D., cites a series of studies conducted by independent researchers who were interested in finding out what adults consider their biggest regrets. During the period of 1989–-2003, adults of all ages were asked the questions: If you could go back and live your life all over again, what would you do differently? What parts of your life would you change? With eleven studies in all, the researchers discovered that the following four regrets appear consistently at the top of the list, in this order, in study after study.

  • Education: 32 percent%
  • Career: 22 percent
  • Intimacy: 15 percent%
  • Parenting: 11 percent%

This is not so say that the majority of people are unhappy and full of regret. Rather, these are the areas where people see the most need (and room) for improvement.

In the studies, the researchers learned that when it came to regretting a career choice, sometimes the regret focused on wishing they had made the kind of choices that would have led them to have a better career, and other times it was focused on wishing they had spent less time on their career, primarily because it impacted intimacy and parenting, two other top-of-the-list regrets. Education and career were closely tied together in the results, as most people wished they had paid more attention in school or had chosen a different educational path, because of how those choices ended up impacting their career.

Career choice can be a particularly long-lasting regret. This is partly because there are so many decisions that make up our career story (everything from choosing a major in college to accepting our first job after we graduate from school). So, when a career doesn’t turn out like we wanted it to we can identify various points along the road where we could have taken a turn better suited to us and we didn’t. That’s hard to swallow. It’s also a fairly blurry regret because when it comes to our careers it’s never just about picking between two clear paths, it’s usually about figuring out a way through a maze full of possible options. I suspect this is why people love career tests: They want to be told there is a single best path, or at least a best two or three, so that their chances of choosing a good fit significantly increase. We don’t like to get our lives wrong.

It’s possible that you have some regrets about choices you have made in the past that you believe are preventing you from moving forward. Possibly you hear yourself saying to yourself:

  • I have no idea what I want to do and I clearly made the wrong choice before so what makes me think I’ll get it right this time?
  • It’s too late to go for what I really want now.
  • I guess I just have to live with my mistakes.
  • If only I could have a do over.

Some people believe it’s best to live with no regrets. I’m not sure if that’s even possible. Even if it were, to do so would be to miss out on valuable information, new insight, countering points of view, and new ways of looking at old facts. “If only this, then that” kind of thinking is actually good for you. At least it can be, if you use it to your advantage rather than marinating in it to the point where you feel stewed in overwhelm.

The truth is we gain meaning and are propelled into action by identifying and naming the alternative choices we’ve made that may not have turned out like we planned. To deny regret is to miss a chance for growth and to make a better choice next time.

When it comes to regret, there are two main ways of reacting to a problem.

  1. Change the situation
  2. Change your mind

When we opt for changing the situation, we take steps to create a better outcome: We go back to school, we build a network, we reach out to people, we research, we apply for jobs, and we start our own business, and so on. We also act quickly.

When we decide to reframe it and change our minds, we rework the situation in our minds so that it no longer seems as bad.

From Fear to Architect: Changing the Situation

My friend Scott took a big risk when he decided to make a career change. In his early twenties Scott graduated from college with a degree in engineering, and then worked in a variety of different jobs in his field. All he really wanted to do however was be an architect and do his own thing. He dreamed about it and talked to people about it, but every time he talked to architects they told him how impossible the field is to succeed in. They told him how long it would take him to go from grunt worker to practicing architect, and that the road was thankless, exhausting, and lacked significant monetary rewards, considering all of the work it required of them.

For seven years he listened to that. For seven years he told himself his dream wasn’t going to happen. For seven years he told himself that he could not afford it, he and his wife couldn’t survive without his income, and they’d never recover if he pursued it.

And for seven years all he could think about was becoming an architect and how much he regretted listening to the naysayers instead of himself.

One day, after imagining himself doing the work he was doing for the rest of his life, he decided that he didn’t care what the “experts” said and that if he didn’t go after what he wanted he would regret it for the rest of his life. He decided to change his situation.

He attended an Ivy League architecture school. He graduated, worked at the school for a couple of years after graduation, and recently he was offered a job at a dream firm doing the work he has always imagined. He and his wife live in a tiny apartment in New York City, he gets excited when he comes home to Boulder, Colorado, because he can get a good shot of tequila for only $20, and if you ask him about his work, his entire face will light up like the Fourth of July.

I have heard a hundred stories like this in researching this topic. The stories of “I can’t do this because . . .” have common threads, which are paralyzing and uninspiring. The magic happens when, for whatever reason, a person realizes the regret is too big to bear and that the story about why she can’t change the situation is old and stale and doesn’t work anymore. She decides that she wants the dream career more than she wants to live with the regret that will only be diluted by harnessing the power of it to get into action.

From Career Hopper to Writer: Changing Your Mind

Seven years ago I hung my shingle out for the first time as a solo entrepreneur. I was excited and I had big ideas of what I was going to do.

I had spent 13 years prior to that career hopping like it was an Olympic sport, and working as a teacher, a counselor and an athletic coach. I had earned two master’s degrees and had completed a teacher education and licensure program. I had served a year for AmeriCorps in undeserved schools and had counseled a variety of different populations from incest victims and juvenile offenders, to runaways, gifted adolescents, underprivileged high school students, girls struggling with eating disorders, career changers and more.

And throughout all of that time I was always an “on the side” writer, taking every writing gig I could get.

My goal with my new business was to write about careers and help people make the switch to do the work they loved.

I had the training, I had the experience and I had a deep love of talking to people on everything related to career.

But that wasn’t enough.

I struggled to get enough clients and my income for that first year was abysmal. I loved the work, but I didn’t love the struggle or living my life in the red.

So I began spending every waking moment studying business, marketing, copywriting and sales and everything else you need to know to make a business profitable. I started applying it to my business and I was having really good success. Before I knew it people were asking me to help them. They wanted help marketing and copywriting and shifting their mindset – all things I had done to grow my business. And they were willing to pay me a lot of money to do it. So much money in fact that pretty soon my career coaching business was a thing of the past and I spent my time as a full time copywriter and marketing consultant.

The problem was that I had set myself up to be unhappy in my work by designing a business that required me to do work I didn’t like and I couldn’t see a way out.

I wanted to be a writer. Period. Instead, I was a marketing consultant who again wrote “on the side”. There was nothing wrong with that work, and I am actually quite good at it, but it just wasn’t the best fit for me. But, I was so convinced that I couldn’t make money writing full time that I kept moving further and further away from my dream…and regretting every moment of it.

I wasn’t able to break out of that business until I changed my mind about what was possible for me. Once I did that, however, the shift was so dramatic and I had so much clarity about what actions I wanted to take that I saw everything in a new light.

After I made that switch, I wrote a book, I began working with clients who were a better fit for me, and I dug full time into a writing business that brings me an immeasurable amount of joy.

When I look back and try to figure out how I could have been so seduced by the money that I was willing to put all of the work I really loved doing on the back burner, I think my desire for safety (money) and my desire to do interesting work that made me giddy with joy just kept duking it out and money kept winning.

Two beliefs had to rise to the top before I was going to allow my situation to change.

  1. I had to reconnect with my values and my beliefs about doing crazy good work.
  2. I had to believe that if I just stuck with the work I loved (writing), and focused on contributing the very best of who I am and the very best of my work to my field of interest (career), that I could achieve the highest level with it. Safety would be a byproduct of that focus, not the driving force behind my actions.

Now that I have set up my business so that writing comes first people ask me if I regret all of the time I spent “off track.”

For a while I did. I was frustrated and angry, and I would often say to myself, Imagine how much further along you’d be if you had just stayed with it and not gone down the rabbit hole. But that was wasteful energy, especially when I think about all of the good things that came from my detour.

  • I was immersed in the world of business and online marketing for six years, I helped clients double and triple their income and learned so much that I can apply to my business and use to help my clients. Whether they want to start a business or need help creating a compelling online presence, I have a lot to offer. I love having problems to solve. When it comes to marketing ideas, I never seem to run out. My entrepreneurial clients love that.
  • I made some fantastic friends in the online marketing space, created cool programs, spoke at interesting events, and hosted unique and game changing retreats for women entrepreneurs. In fact, some of my dearest friends in the world right now are the ones I made while doing that work. When I think about what my life would be like without them I would take that detour again any day.
  • Going through all of this has given me a surplus of tools I can share with my clients who are trying to reinvent themselves and their careers.
  • I now have a tremendous amount of patience for people who feel stuck, people who want to make a change and can’t see their way through. I always had the training and hundreds of hours working with clients who were trying to find their ideal career or place in the world to draw on; however, having now gone through a similar experience myself adds texture I would not have had otherwise.

So, when it comes to regret the goal then is to accept regret as part of our journey and then move past our regrets by identifying the ones that may be holding us back, looking deeper into how we describe them to ourselves, and acting quickly to change the situation. Here’s a simple process you can follow to do that.

A 4 Step Process for Moving Past Career Regret

Step 1: Take out a blank piece of paper or open your journal and write down every “if only” that comes to mind when you reflect on the path your career has taken.

Example: “If only I had done this than thisnever would have happened.”

Example: “I chose blank when I should have chosen blank.”

Step 2. Now that you have made a list of all of the “if onlys” in your mind, you are ready to look deeper into the regrets to see how there was more than one way the event in question happened. Respond to the following on your paper: How might your situation have turned out worse if you had chosen the other path? How have you used comparisons to other people to allow the regret to grow? How could you reframe your regret, or what can you do right away, to show yourself that changing your situation is far more important to you than hanging on to your regret? How will you know when you’ve truly let go of the regret?

Step 3. The great thing about regret is that within that emotion exists a backlog of lessons that we’ve likely learned without even being conscious about it. Next, contemplate all of the perceived negative outcomes you’ve experienced throughout your career. Maybe you were fired or demoted, maybe you really wanted a job but weren’t offered the position, maybe you were offered the job but turned down the offer and then wished you hadn’t. Write down what happened and then find the lesson and how you took that lesson into other areas of your life and you used it to your benefit.

Step 4. Now let’s turn your every “If only” into a “Now I”. Whatever regret you have, whatever “if only” statement has been holding you back, pretend that it no longer has the control. You do. Now is what matters. Use your regret as a springboard for further action. Research your options, but don’t get stuck there. Act quickly. Hurl yourself headfirst into the unknown and don’t be so worried about getting it right that you stop yourself. Concern yourself only with who you are today, in this moment, and act from that place. If you do something and it turns out badly then you’ll still be better off. Not so if you leave a situation undone.

Make a plan for how you are going to move beyond your regret and then do it right away. The most successful people are those who kick themselves the hardest after they make mistakes and get over their intense regret faster than anyone else. After that, they take immediate action. Those are the people who trade in worry about how it could have been for careers that fit who they are today and are ultimately able to reinvent their careers without the baggage of regret slowing them down.

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