Dreaming Backward – Dottie Herman

Dreaming Backward

Dreaming Backward

What is dreaming backward?  To me, it is beginning with the end in mind. At the end of each year, we are all thinking about what changes we want to make personally or professionally.  Is it time to pivot or will you stay the course.  If you are thinking about pivoting in your professional career it can be a scary decision. Sometimes, not making a career change can be even scarier, especially when you are suffering emotionally or physically from your current situation. If you aren’t sure about pulling the trigger, take a few minutes to assess where you are.


  • Are you still passionate about your work?
  • Are you being impacted by the layers of stress you carry from your job?
  • Do you feel you’ve outgrown your current position?
  • Are you required to go back to the office and you loathe the idea?


A lot of people know they’re unhappy, but they can’t pinpoint the reasons. Even super successful people who have met every single career goal can feel this way.  So many people drink the “follow your passion and everything will fall into place” Kool-Aid. But at Cal Newport, a scientific researcher says that those who “follow their passions” statistically have a lower probability of finding long-term career fulfillment than those who leverage existing career capital when making a shift. If this is true, you’re much better off pivoting into roles that leverage the career capital you’ve already built up over the years and drawing upon these areas of expertise in new and creative ways.


So, if you’re seriously thinking about making a change, ask yourself these three questions: “Why do I want this? Why do I think this new career will make my life better? What might the downsides or risks be?  You may discover things aren’t so bad where you are, or you might realize the very thing you are supposed to be doing. Also, a very important question to consider is whether you are going to be able to leverage your skills, your contacts, and your professional brand to make a successful transition?


Even if you are lacking certain skills that you need to be an attractive candidate for this new type of role, such as certifications, classes, or a license, sometimes, it’s entirely within reach. It could be a simple matter of taking an online course and gaining some baseline proficiency so that you can confidently move forward. Begin with the end in mind with your action plan. I call this dreaming backward. What’s your primary goal and ideal timeline and what steps did you take to get there?


Set short term goals and become relentless at meeting them. Give yourself daily or weekly tasks so that you know what, exactly, you’ll be doing when you sit down in front of your computer in the name of “career pivot.” You don’t want to wing this. As you complete these tasks, you’ll also likely notice how small steps tend to have a snowball effect and give you both momentum and confidence that this is, in fact, a very real possibility.


Get your people on board, especially the ones you know will always have your back. I like to refer to these people as your tribe. Pick your most trusted contacts and enlist their help. Be specific. Ask for what you need. Communicate clearly and tell people how they can help you the most. People are more generous with their time and input than you think, especially when you show interest in them and acknowledge or validate something they’re doing professionally. Everyone wants to feel acknowledged. After you build a rapport, then you can ask for a favor or a bit of their time. And then use their input. The biggest reason people stop short of ever making career pivots is because they’re scared. Terrified. And I get it. Change is terrifying. Fear of the unknown is terrifying. Fear of failure? The worst.  But it shouldn’t stop you from becoming the best version of yourself, especially when it comes to your career. Even when things look scary, remember, you’ve already survived one hundred percent of the worst days of your life. You will get through this too. All it takes is the courage to do it.

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