A Can’t-Mess-It-Up Checklist For Your Career Change



Quote Artwork Print by Designed by Wilma

My last Can’t-Mess-It-Up Checklist proved so popular, I couldn’t help but create another one for those on the cusp of a career change!

Looking to make a change in your career, but are unsure where to start?

Or maybe you’re thisclose to putting a new career plan into action?

Here’s a simple, bare-necessities can’t-mess-it-up checklist to show your career change who’s bossand if anyone tells you that you *have* to have anything else, they’re wrong:

  • Put on your Nancy Drew hat and view yourself with curiosity. View the whole thing as an experiment, with you playing detective. Do what you can to distance yourself from the outcome and look for clues everywhere. What are your enjoying? What feels really hard? What proves to be a challenge? What comes easily to you? Start a new notebook or document, write down your findings and review ’em on a daily, weekly, or bimonthly basis. Keep tweaking as you go to build on your wins and attract more of what you’re seeking. Resources: Your Win Book; I Quit My Day Job: The Updates; 10 Ways to Discover Work That Feels Like Play
  • Live in the Questions – but not forever. You must must must allow yourself to spend some time dreaming, researching, and planning. So as not to spend infinite time on the dreaming, researching and planning, set a deadline for yourself and write it on your calendar – a month or two should be more than enough before it’s time to step on the gas and start really taking action. Resources: Living in the QuestionsMaybe It’s Time for a Plan, Some Research, and Living in the Questions
  • Build momentum by doing something every day.  Make it a habit of getting your work done in small chunks each day. Keep your eyes open for the times you find you’re “wasting” time – whether it’s watching a TV show you don’t particularly like, doing chores that could be delegated (or not done alone), or spending hours on Facebook or Candy Crush. 

    I had a client decide that her business time was post-dishwashing after dinner every week night. At first, she had to force herself to go to her studio and shut the door, leaving her husband alone to watch TV. She’d set a timer for 45 minutes and would have full permission to leave once that timer dinged. Some days were torture and others would feel so fun it’d lead to another 45 minutes on the timer. Eventually she said to me that going to her studio after washing the dishes was automatic – she found herself there one night without remembering how she got there! That’s the best.

    If you’re using the excuse that you have brain drain at the end of the day, put on your Nancy Drew hat and just see if you get an energy boost after doing 15 or 20 minutes of your career change work.  I think of it like exercise – the worst part is always getting on your sneakers and getting out the door, but once you’re 20 minutes into your run or class, you’re happy to be there! Resources:  Pomodoro Technique (to start thinking in 25 min chunks of time instead of waiting for free hour(s) to fall from the sky); Lift (an easy way to get into the habit of doing something every day-ish and tracking your progress); Productive Flourishing’s Free Planners (made for creatives!); Anti-Social (a great way to block distracting sites); Just 15 Minutes/Day to Becoming a Full-Time Entrepreneur
  • Make your career change a priority. If you view this as a “hobby” or “a personal indulgence” or something that isn’t of the utmost importance – for your health, your sanity, your well-being, and the way that you interact and care for yourself and your loved ones – then that mindset has gotta stop!My favorite exercise to do here is have you write a Welcome letter from the CEO of your company (you!) to the first employee of your company (also you!), speaking to the values + expectations + responsibilities that you have. Even if you’re not looking to be self-employed, you need to view this time as one where you’re the boss. What are you going to work on? When are you showing up? What will it give you – emotionally, physically, financially – when you make it happen? Resources: My 10 Favorite Resources to Help You Discover What You Wanna Be When You Grow Up. Pick one and work through it!
  • Feel the career fear – and do it anyway. At any given moment, you might feel like you’re a lost cause, or that you can’t focus or follow through, that you’re a Jane of All Trades and a master of none, that you’ve already made too many career changes, that you’re not actually special enough to make it work. Those Vampire Voices (I call ’em that ’cause they suck the good stuff out of us!) are ones that I hear most often from my clients and ones that I hear myself – you’re not alone! But let’s stop using ’em as excuses and instead use ’em as fuel to feed our career change “investigation” Resources: Feel the Career Fear – and Do It Anyways (it’s a free webinar I did and lots of resources to go with it!)

Seriously – that’s it! The most important thing I can remind you of is to be nice to yourself throughout this process!

Also, don’t rush it, do what you can to release the pressure, and for the love of all that’s holy, take action. Tangibly doing something – anything! – that you want to explore as a career is way more valuable than spending weeks or months or years (over)thinking about it.

Any questions about pending career change – or the ones (yes, plural!) that I’ve made? Anything you think I missed? That’s what the comments are for!




  1. says

    This is a great resource, thank you!

    My business is having a “dark night of the soul” right now so I’ve spent the past week just diving in and exploring what the next step is.

    I’ve got your “10 Ways to Discover Work That Feels Like Play” videos sitting in my inbox, but I still haven’t watched them, yikes! :)

    • michelle says

      Ooh do it do it do it, Nela! I promise those videos will make the diving/exploring waaaaay more productive and (hopefully) fun!

  2. says

    I have overcome the first hurdle by giving myself permission to start looking for a new career…then TERROR walked in, how will I pay for my mortgage? What about health insurance? What about losing all of my vacation time? What if, what if what if?

    Thank you for this post, I am going to start to rethink the process while choosing to be afraid and do it anyway. I am miserable at work . Each day, I muster up and face the day, fantasizing about winning the lottery. Instead I am going to use this time to plan and prepare for my career change!

    Thank you!

    • michelle says

      Oh yes, I know that TERROR all too well. I call it our Vampire Voices ’cause it sucks the good stuff right out of us! The good thing about it, though, is that it points us directly to what’s in our way…so we can break it down and get through it! I’d encourage ya to put on your Nancy Drew hat and do some investigating/brainstorming/experimenting. Start collecting the “clues” for what you’d do to pay the mortgage, how you can get health insurance, what you’d need to do so you don’t lose vacation time? Vampires hate real facts – they’d much rather you work yourself up with things you THINK might happen! :)

      I’m in your corner, Kelly!

  3. Libby says

    Michelle, I think you can read my mind!!! Thank you for all of your encouraging words and sharing your journey. It is so incredibly inspiring to read about your journey and I try my best to keep a positive mindset and know that I too can make it through my career fear and build a future I am proud of. As always, thank you thank you!

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