Most people would rather not spend time thinking about their regrets yet an unexamined regret can haunt us more than the regret itself.  If we don’t take the time to learn from our regrets, we risk repeating the same behaviour and undermining our self-confidence. While I’ve written before about how quitting your job can be your best decision, today I’ll also share a few regrets and what I’ve learned that can help you in your own career transition.

Regret #1: I didn’t realize how important financial independence was to me.

Money is important to all of us, no matter how much we might like to avoid that fact.  Before I made the decision to resign from my career in financial technology to become a professional coach, I saved up my money to support me through my first year.  I hoped to be covering my share of the household expenses after that and it came as a harsh surprise when I couldn’t do that as soon as I’d planned.

I didn’t recognize it immediately, yet I found it very upsetting to have to rely financially on my spouse.  Every day I was unable to cover my expenses was another day that eroded my self-confidence in my new career. Eventually I realized that I didn’t have to put myself in such a stark position anymore.  I was able to take on a couple of contracts to help pick up the financial slack and they didn’t disrupt my career transition as much as I’d feared they might.

If I could do things over again, I wouldn’t have waited so long to pick up side work to ease my financial worries.  Financial independence was more important to me than I initially thought and honouring this core value was essential for maintaining my self-confidence and managing my anxiety (both which are vital to successful career transition).

If you’re considering career transition,

  • What are your top 5 values?
  • How can you honour each one of them as you make your transition?

Regret #2: I didn’t know my process to create steady, positive change before making my transition.

Here’s the paradox of my career transition: if I hadn’t done it the way I had, I may not have discovered my process to create steady, positive change in how I experience work and develop my business.  However, If I’d already known my process to create positive change before I left my first career, my transition could have been a lot easier and more enjoyable.

Having taken what seemed like a giant leap from financial technology management to professional career coaching, I was left hanging in the air waiting for a mythical net to appear (as it turns out, “net” is just a euphemism for “hard work”).  I felt like I was falling down an endless rabbit hole – I was highly anxious and more stressed than I wished to be even while I trained to do the work I would grow to love.

In an effort to manage my runaway anxiety, I identified certain habits or practices that helped me calm down in the moment and re-focus my attention.  These practices and accompanying mindsets would evolve into my “process” to create positive change, and now I work with others to develop their own process to help them manage anxiety and approach their own career transitions with trust and creativity.

If I’d known then what I know now, I’d like to have used my process to help me transition in a way that set me up for the most success, and increased my self-confidence instead of diminishing it.

  • What beliefs or assumptions do you make about what career transition is meant to be like?
  • How important do you think it is to set yourself up for success in career transition?
    (for more help with this, download your free guide to “Develop Your Process to Create Positive Change” at the bottom of the Process-Based Living Home page)

Regret #3: I could have had more fun.

At the end of the day, my career transition has worked out.  In fact, I think I will continue to transition in my career for a long time to come.  Transition is about changing states and there’s no shortage of that in my work, business, or life anymore.  What I regret is that I didn’t, or couldn’t, take more time to appreciate everything that went on during my initial years of transition.  I’ll recap these:

  1. Somewhat like The Grinch Who Stole Christmas, my soul grew three times bigger in the process of changing my career and discovering what truly makes me come alive (helping people develop stronger presence and effectively create positive change in their work).  I have more potential than ever before.
  2. I’ve been able to do all the little things I used to dream of, such as going for a walk in the middle of the day under a warm sun and tall trees. I finally learned how to meditate, having had more time for meditation classes.  Occasionally I linger over lunches, worrying less about having to run back for this meeting or that.  I don’t get to do this all the time but these small delights make me realize how much I restricted myself in my old career.  If I’d recognized that sooner, I could have made different choices to enhance the quality of my experience.

The work of growing my soul and having more personal freedom was both awe-inspiring and challenging.  I took it all very seriously and I know I missed out on many precious moments of lightness throughout.  I’m working on being more grateful each day so that I don’t miss another moment to enjoy what I’ve created, and continue to create for myself.

  • How serious does your career transition seem to you?
  • What can you be grateful for nonetheless?

And that’s all I have to say about regret in my career transition.  The rest is learning and forward-moving.  For those of you who are contemplating or already in career transition: remember to honour all of your values along the way, identify those habits that will make it easier for you, and don’t forget to have fun at such a unique and meaningful time in your life.