Riding Two Horses

Changing careers: That sweet daydream you entertain when your workday is monotonous, the boss is acting like an unmentionable body part or you are too stressed to think straight. For many, the dream stays only as a dream, either because they truly enjoy what they do or they don’t think its possible to change. But there are those for whom career transition is real, either because of a watershed event like a layoff or retirement, or through the gradual realization that there is something more desirable to do. In these cases, how does one make a career transition, moving from one focus to another? In other words, how do you fundamentally change what you do for a living?

A very wise guru, Jeffrey Armstrong, once counseled me on career change through the metaphor of riding two horses. Imagine you are riding a horse. It’s a good horse but over time you find yourself wanting to find a new way in the world. You need to ride a different horse. But you can’t just jump from one horse to the next without thought or planning. If you did so, the horse you desire will likely run away from you, leaving you flat on the ground. No, to change horses you first must bring the new horse to your current path, allowing it to gallop side by side with the horse you’re on. In effect, you are dividing your time and attention in two, maintaining what you have always been doing while nurturing what you want to leap to when the time is right. And then, when the new horse – the new profession – is perfectly in sync with where you are, you leap, riding forward on your new path.

Timing, as it is with many things, is crucial. Leap too early, as I noted before, and you fall flat. Wait too long and the future might slip away. Career change requires good timing and, of greater importance, guts for that career leap is a leap of faith, no matter how clear-eyed and effective your planning may be.

Charlotte Seager, writing for The Guardian in October 2014, outlined a few steps for professional transition, through the advice of career experts. One of the experts endorsed a gradual approach to career change. In other words, don’t jump too early or you’ll fall flat. Another cited belief; you have to believe it can happen and begin speaking of yourself in terms that make it “real” in your mind as well as the minds of those you encounter. It reminds me of the old adage “Fake it until you make it.”

I’m currently riding two horses professionally. Since establishing my consultancy in late 2011, I’ve focused on the work I came to specialize in during my corporate years: communication strategy and program design for large scale, transformational change (M&A, restructurings, culture, growth). This work requires heavy leadership interaction and I was always fascinated by the intersection of company evolution and the role leaders play in making it happen successfully. Working with leaders was something I always enjoyed, and many times it was the quiet conversations I had with them about strategy, change and leadership itself that made me feel most at home in my work. I found myself evolving toward leadership issues and competencies more and more. My next career iteration began to appear: leadership coaching and branding. But how could I bring the new horse to my path? Through training. I undertook a rigorous, multi-month leadership performance coaching course certified by the International Coach Federation. It was enlivening to learn a new skill and at times a bit terrifying. I wondered if I was honestly well suited to this new competency. In the shadow of the joy and the fear I experienced, I saw the new horse come into view, slightly behind and alongside of me. There was something new for me to explore, something that would give me another chance to mine what interested me and give me space to contribute in novel ways.

Yet as exhilarating as the thought of changing horses was, and is, it is also tiring at times. Riding two horses is both a career challenge and an endurance test. It’s a shift from what is comfortable. What keeps me going when I contemplate all there is do to maintain my current focus and move forward is the excitement I feel in tackling a new competency, a new business model. Will I ultimately succeed? Who knows? But it sure is a privilege to try.

For now, I’ll ride both careers as hard and fast as I can, believing that one day I will change horses and ride forward to whatever comes next.




  1. Ed Henkler April 22, 2016 Reply

    Great post, Kristina.

    I like the two horse metaphor. Two thoughts are while it’s not necessary, finding a second horse aligned with personal passion can accelerate progress. It’s also after the fact but before grabbing that second horse, I’d strongly recommend building a vibrant network and paying things forward as much as possible – builds an advocacy network that wants to help you as you transition.

  2. Author
    K. Dipalo April 24, 2016 Reply

    Ed – Thank you so much for your comment. You are absolutely right that having a vibrant, and dare I say loving network in place is vital. Knowing that you are ready to leap is one thing; having people there to make sure you land right makes all the difference.

  3. Chupacabra May 21, 2016 Reply

    Failing to do two fairly simple things that most everyone can do, not failing at two hard things because you tried to do both.

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