8 Questions to Ask When Your Career Plans Get Derailed

There are a bazillion reasons why people’s best efforts run off track.

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Curt Rosengren
One of the things I have learned from watching people pursue passion in their career is how incredibly common it is for those efforts to get derailed at some point along the way. There are a bazillion reasons why people’s efforts run off track. Sometimes the path gets unexpectedly challenging. Other times the demands of other parts of life get in the way. Sometime fear kicks in and takes over. Often, it’s just hard to stay focused on it for the long term, and people’s attention and action start to wander.

[See 15 essentials for getting hired.]

Whatever the reason, if you ever wind up off track as you pursue your passion, take heart. You’re in good company. It happens a lot. The important thing is not whether or not you get derailed, it’s what you do when you realize that it has happened. Here are several questions to ask to help you get back on track:

What happened? Spend some time exploring why you went off track. Identify the different pieces of the puzzle so you can learn from them and apply that insight to where you go from here. Do a situation assessment. Here are some questions that might help:

  • When did I first start getting stalled? Why?
  • Was it a conscious decision, or did I drift off track because my focus went elsewhere?
  • If it was a conscious decision, what was the rationale? Might there have been other options?
  • Were there any ways I might have been able to keep moving in small steps towards the goal?
  • What can I learn from what happened? How could I put that to use in the future to a) help me move towards my goal and b) help me stay focused and on track?
  • [See how to use your negative thoughts for good.]

    What does “on track” look like now? This is basically a check-in to get clear about where you want to be aiming your efforts right now. It may still be in the same direction. Or what you learned along the way may have resulted in a change of direction. Make sure you have a solid grasp of where you want to go. (If you don’t, then gaining that clarity is the next step in getting back on track.)

    What is stopping me? Take a look at your current situation and explore what’s holding you back. The better you understand what’s keeping you from moving in the direction you want to move, the more potential you have to find ways around those obstacles. Flesh out your understanding of what’s stopping you with questions like:

    • What logistical obstacles are standing in my way?
    • What mental/emotional obstacles are standing in my way? (e.g., I’m too frustrated. I’m too scared. I’m too skeptical.)
    • What obstacles of clarity are standing in my way? (e.g., I don’t know where I’m going. I don’t know how to get there.)
    • [See the question that could change every average day.]

      How can I get around those obstacles? One of my favorite ways to approach this is to say, “Let’s say you had no choice but to make this happen, how could you do it?” It’s easy to look at a challenge and throw our hands in the air and say, “I can’t do it.” But removing that as an option–at least for the sake of exploration–forces you to get creative and really explore the possibilities.

      What assumptions am I making? Are they valid? If we’ve bumped up against a challenge on the path, it’s easy to generalize that into an assumption that whatever we encountered is insurmountable, or to characterize the entire path by that challenge. Are there any assumptions you’re making that aren’t completely valid?

      What is the biggest small step I can take next? A big piece of getting back on track is just doing it. Taking a step, then another, and then another. Action creates momentum. It might be worth spending some time looking at the various small steps you could take. When you get a chance, write them down so you have them ready for you to choose from when it’s time to jump back in.

      [See how to face down your fear of career change.]

      What resources do I have that will help me build that momentum again? This could be other people (friends/family/colleagues/a mentor/a coach) or information and inspiration sources (written, audio, or video).

      If I were to create a system to help me maintain that momentum and stay on track, what would it look like? What helps you stay on track and how do you consciously incorporate that into the picture? Who could support you? How could you build accountability into the system? What are the danger zones for you, and what are some ways you could minimize their risk?

      If you get derailed, don’t treat it like the end of the line. It’s only the end of the line if you decide to stop. Instead, pause, take a deep breath, and start asking questions. Get clarity around what happened, identify possible ways to address your challenges, and start taking action again.

      After years as a professional malcontent, Curt Rosengren discovered the power of passion. As speaker, author, and coach, Rosengren helps people create careers that energize and inspire them. His book, 101 Ways to Get Wild About, and his E-book, The Occupational Adventure Guide, offer people tools for turning dreams into reality. Rosengren's blog, The M.A.P. Maker, explores how to craft a life of meaning, abundance, and passion.