top of page
  • Writer's pictureKristin Schuchman, Career Strategist

How to Prepare for a Career Transition

Updated: Mar 30, 2021

Before you change careers, put everything in its proper place

Career transition can be a deeply personal endurance test – most of us experience periods of emotional upheaval, self-doubt and, depending on our post-work experiences, varying levels of trauma. Job changers rarely express these feelings out loud since an optimistic, expansive mindset serves us when we’re navigating a new career path. The thing is, if we continue to bury the self-limiting negative beliefs, they have a way of surfacing at unpredictable times to sabotage our entire career change.

If you are still working an unsatisfying position, the pretense of positivity may be exhausting you. Or, if you’re unemployed, you may hate being continually asked how the search is going. You may say, breezily, “I’m enjoying spending quality time with the kids, and there are several interesting options that I am exploring.” You wish you could groan and say frankly, “I’ve actually been over-indulging in true crime paperbacks and reorganizing my closets.”

To offset the emotional challenges, take stock of the resources you have at your disposal; assess your self-care needs; and surround yourself with fun, optimistic people who reliably offer moral support. The goal is to keep yourself energized and focusing forward.

Like a good road trip, you will travel more smoothly during a career transition if you prepare properly, collect the gear you’ll need, and outline an itinerary to keep you on track. Follow the checklist of tools below to ensure a safe and productive journey.

Here’s how to use the Career Change Itinerary:

  1. For each item, write down in the space below it your notes for manifesting that “tool.” For instance, to create an attractive work area, you may make a note to visit IKEA to buy a desk or a new lamp – whatever you need to create a proper work space.

  2. Next, circle number 1, 2, 3 or 4 with 1 being the highest priority and 4 being the lowest.

  3. After that, write down the date on which you can acquire that tool. (if you don’t plan to implement the tool, cross it out).

  4. Once you’ve acquired the tool or made it a regular habit, put a checkmark in the space to the left.

While I understand the impulse to dive in and get started right away, pace yourself. Just know that you will have more success if you cultivate and build the tools listed here, so print this page to remind you to return to this section.

Work steadily on this checklist, but don’t let its lack of completion keep you from moving forward. You can take practical steps towards your career transition while using and building on the tools you think our helpful. Take advantage of your internal momentum as it builds!


A. Practical Elements

First, create and stock an attractive area in which to work. Only you can decide how organized it needs to be. (Einstein said, “If a cluttered desk is a sign of a cluttered mind, of what, then, is an empty desk a sign?”) Most importantly, put things in place that remind you of people you love and that keep you inspired. Put at least one thing on your desk is tied to someone you admire – a photo, a paperweight or some other object that puts you in mind of a specific person.

__ Attractive Work Area

___________________________________________ 1 2 3 4

Set up a home office area and make it a place where you want to spend time. Decorate with motivating quotes, pictures of loved ones, plants – whatever inspires you.

__ Dedicated Work Space

___________________________________________ 1 2 3 4

Create a space that will allow you to work without interruption, preferably a place where you can close the door and work quietly. Even a closet is fine as long as it’s a place where you can store your Career Search Binder and other career transition “tools.” Make it as clear as possible that people you live with should respect your work area; they should not remove materials when you are gone or leave behind their discarded banana peels and yogurt containers.

__ Do Not Disturb Sign

___________________________________________ 1 2 3 4

Slap that baby on the door knob – if you have the luxury of a door – when you’re working in your space. People will interrupt you as much as you allow them, so don’t be afraid to be firm about your time and space needs.

__ Career Search Binder

___________________________________________ 1 2 3 4

Create a binder with 11 sections: one for each step outlined in this book, and one section for calendar pages. Use Tul calendar pages and accessories (available at Office Depot) to build a custom career binder that will work for you.

__ Money/Temporary Income

___________________________________________ 1 2 3 4

Most of us aren’t Rockefellers and need to bring in at least some income to cover our basic expenses. Pick up a part-time job if you can swing it. If you must work full time, be sure to carve out at least four hours of uninterrupted time on the weekends for your career journey.

__ Budget

___________________________________________ 1 2 3 4

We think it’s helpful to outline at least a rudimentary budget to see where you can cut back on spending to avoid full-time employment, if possible. At a minimum, it is a useful exercise to give you a sense of how much you would like to make in the coming years. Also, it can help you determine if options like going back to school or completing a training program are possible.

__ Day Timer

___________________________________________ 1 2 3 4

Treat yourself to a novelty egg timer shaped like a cat or an actual egg to decorate your work space and track a set amount of time per day for your career-transition work.

__ Resume

___________________________________________ 1 2 3 4

Don’t want you to worry too much about polishing your resume yet, but dig up your latest draft so that it’s easily accessible if you do need it. Review it to remind you of your accomplishments and boost your confidence.

__ Other:

___________________________________________ 1 2 3 4

B. Technology Tools

In the last 20 years technology has changed drastically how we embark on a career-transition journey, start businesses, search for jobs, hire and evaluate employees, and do our work. In the last five years social media has begun to play a primary role in how people are assessed and evaluated, even before they are asked to follow the preliminary hiring steps. While this might seem disconcerting, it can actually provide you with possibilities to shine as you showcase your achievements and connect with others who can help pave the way to your new career.

__ Basic Computer Skills

___________________________________________ 1 2 3 4

Many community colleges and workforce centers offer free and low-priced computer classes. At the very least, brush up on Microsoft Word and Excel. For extra mileage, add a database program, and if you are creatively inclined, Adobe Creative Suite programs like InDesign, Illustrator and Photoshop. (Private art colleges and community college often offer reasonably-priced classes in Adobe products.)

__ LinkedIn

___________________________________________ 1 2 3 4

Because 93% of hiring managers use LinkedIn and a staggering number of people (over a billion as of January 2018) are using Facebook, it just makes sense to join the bandwagon. (There are several outside-the-box ways to use LinkedIn for career exploration and job search that may surprise you. You'll learn more about that in some upcoming posts.)

__ Updated list of “Tour Guides” and Other Contacts

___________________________________________ 1 2 3 4

Create a spreadsheet of your contacts and indicate which ones are your metaphorical “Tour Guides.” All of your contacts are important, and you’ll want to reach out to them in due time. Your Tour Guides, however, are those special people who either completely have your back and/or can introduce you to careers and fields you wish to explore further.

__ Other Social Media (Instagram, Twitter, etc.)

___________________________________________ 1 2 3 4

Your need to engage with social media will depend on your industry and personal preferences. If you are uncertain about your need to engage in social media engagement, talk to other people who pursue careers you admire. Stick to social media you enjoy and that allows you to be authentic and doesn't suck an disproportionate amount of time. Avoid pointless conflicts and never give trolls power over your mood or spirit.

__ Teleconferencing and Remote Collaboration Tools

___________________________________________ 1 2 3 4

Even before COVID forced workplaces to step up their work-from-home technologies, mastering online conferencing and collaboration was increasingly critical. The more expertise you have in these tools, the more smoothly you will make the case for your ability to easily contribute in remote work settings. These tools include video conferencing tools like Zoom, Google Meet, GoToMeeting, and Microsoft Teams and online collaboration applications like Slack, Dropbox, Google Drive, Microsoft SharePoint, among others.

__ Calendar App

___________________________________________ 1 2 3 4

Unless you’re religiously committed to a paper calendar, consider using an online calendar tool. We like Google Calendar, but Microsoft Outlook and Apple’s iCal are also popular. If you’re a smartphone user, download the corresponding calendar app so you’re ready to schedule something wherever you are. Whether you go high tech or kick it old school with a paper calendar, be sure to block out time for self-care, reflection, coffee dates and getaways. (Keep reading to find out more about these.)

__ Other:

___________________________________________ 1 2 3 4

C. Spiritual / Emotional Support

Consider the tools that fortify you internally and invite joy, peace, and meaning into your process. Review the things that have helped you through other challenges, from journaling to golf. Find and strengthen your connections to people who can both share the inside journey and support the outward tasks of the search. In addition to supportive family and friends, you might consider working with a career counselor or coach. They can help you clarify a career goal, overcome doubts and fears, and provide practical tools such as resume and interview help. Most provide a free phone consultation and have personal websites. We can provide more help and support if you reach out to us before you feel stuck.

__ Motivational Books

___________________________________________ 1 2 3 4

My favorites include Jen Sincero's You Are a Badass, Martha Beck’s Finding Your North Star, Carol Eikleberry’s The Career Guide for Creative and Unconventional People, and, if you’re entertaining the idea of starting a business, Chris Gillebeau’s The $100 Startup.

__ Uplifting Music

___________________________________________ 1 2 3 4

We don’t know about you, but nothing gets our mojo going like a lively tune. When I am feeling blah, I crank up British pop or punk music – Chumbawamba’s Tubthumping always gets me going.

__ Inspirational Movies

___________________________________________ 1 2 3 4

It's my strong conviction that we need stories like we need food. Even silly movies can provide guideposts to help us figure out challenging conundrums or just take our minds off our problems for the moment. (Thank you, Will Ferrell.)

__ Engaging Podcasts

___________________________________________ 1 2 3 4

Podcasts like Serial have kick-started the audio medium, and we think it’s fantastic. You can learn all kinds of things while folding your laundry, walking the dog, or drifting off to sleep. We get re-energized by the Ted Radio Hour, Fresh Air, and The Jealous Curator.

__ Journaling Notebook

___________________________________________ 1 2 3 4

A character in Bram Stoker’s Dracula says, “Journaling is like whispering to one’s self and listening at the same time.” It may seem a little woo woo, but writing does have the unique power to reveal what you’re really thinking.

__ Coffee Dates with Supportive Friends

___________________________________________ 1 2 3 4

I’m not sure this needs much explaining, but it is something that we don’t always think to chisel into our schedule, especially if we’re spending a lot of time at home. Make time for your friends and don’t hesitate to ask for their help and their insights about you. You may discover some things you never knew.

__ Career Counselor

___________________________________________ 1 2 3 4

Your friends and family, even if they’re incredibly supportive, can help you only to a point. When it’s time for objective assistance with a career transition, career counselors can help you sort through the torrent of thoughts that can overwhelm and befuddle even the most together person. Ask your therapist, if you see one, for a referral to a career counselor or check out Yelp and If you don’t see one in your city, don't despair. Several career counselors and coaches, including myself, offer Skype and phone sessions.

__ Getaways

___________________________________________ 1 2 3 4

We are big fans of road trips, but if this proves impossible, little day trips are invaluable at this time to open up your thinking. Take yourself to those places you only take your sister when she’s in town and try to appreciate them like a tourist. Even city parks are wonderful places to encourage mindful appreciation of the world and give yourself a psychological reboot.

__ Reflection Time

___________________________________________ 1 2 3 4

This can be done during your Getaways and your Journaling, but it also can be done by waking up before everyone in the house to take advantage of that precious silent time. Some of the exercises in this book invite reflection and you will need uninterrupted time to do it. Use your calendar app or planner to schedule reflection time and promise yourself you'll honor your appointment.

__ Creative Expression

___________________________________________ 1 2 3 4

If you’re the least bit creative and you’re not making time to express your gift, you have the potential—we truly believe—to become a menace to society. No, you may not necessarily be sending scary manifestos to the newspapers or slapping a cop, but you do run the risk of turning your creative frustration inward. This can lead to depression or anxiety. If you’re a social media fan, a great way to commit to a creative outlet is to take a photograph or draw a picture daily (or weekly) and post it on Instagram, Twitter, and/or Facebook with a descriptive, original hashtag like #picturesofwindowsinportland.

__ Mindfulness

___________________________________________ 1 2 3 4

Humans have a way of tuning out from the world when asked to perform routine tasks that no longer require higher level thinking. Mindfulness is a Buddhist-inspired practice of paying extra attention and seeing the world like a child does, as if you were experiencing things for the first time. Meditation and yoga, while the most obvious mindfulness practices, aren’t the only approaches – walking, painting, swimming, or just noticing a beautiful view are all excellent mindfulness habits.

__ Self-Care

___________________________________________ 1 2 3 4

Arguably all the tools listed in this section are examples of self-care, which is best approached as an overall mindset. By prioritizing your needs for exercise, self-expression, time to yourself, time with friends, and a mindful approach to life, you will improve your cognitive reasoning abilities and lower your stress and anxiety level. For more self-care tips, take note of the ideas next to the little "gift" icons throughout this book.

__ Other:

___________________________________________ 1 2 3 4

D. Community Engagement

If you are unemployed, you may miss your daily interaction with co-workers. Belonging to communities, even meeting your neighbors, provides personal support at a challenging time. Community engagement can surprise you with networking opportunities to augment the job search. If the thought of networking puts you off, try to think of it as “meeting interesting people.” You might discover that it's more fun than you imagined.

__ Professional Association

___________________________________________ 1 2 3 4

Attending the meetings of professional associations and networking groups is a great way to get yourself out in the world to make contacts and learn more about alternative careers. Collect business cards and follow up promptly to set up coffee dates and connect on LinkedIn and other appropriate social media.

__ Neighborhood Involvement

___________________________________________ 1 2 3 4

Neighborhood associations are often the source of outstanding community projects, like farmers' markets and street fairs, that offer a robust way to forge connections and build marketable skills. Kristin helped start a farmers’ market in her neighborhood in Portland, an experience she counts among her proudest accomplishments and the source of several lifelong friendships.

__ Strategic Volunteering

___________________________________________ 1 2 3 4

Find a cause about which you’re passionate and offer to volunteer a skill you are looking to build. Nonprofits and grass roots political organizations are constantly looking for people to help with marketing, social media, events, and community outreach. Be willing to help out with less flashy tasks like stuffing envelopes or making phone calls. Once they see you’re consistent, reliable, and offer good ideas, they’ll likely give you more challenging responsibilities.

__ Church/Spiritual Affiliation

___________________________________________ 1 2 3 4

When I go on road trips to clear my mind, I actually think of the places I stay as “temples". These are the homes of good friends and family who know me well and love me unconditionally. If you have a place of worship, consider ways to volunteer your time and skills there to meet more people and build deeper relationships that will serve you during times of extreme challenge. If you don't have a place of worship, Unitarian and Quaker churches are incredibly welcoming to people of all faiths and beliefs. Your spiritual place doesn't have to be a church, synagogue, or mosque; a Buddhist temple, LGBTQ community center, or a martial arts studio might be a place that feeds your soul. These are just a few organizations where communities of kindred spirits flourish.

__ Interesting Meetups

___________________________________________ 1 2 3 4

Whatever your interest, there is a Meetup for you: Cannabis Startups, Lesbians Who Podcast, or Oregonian Surfers, to name a few. Meetups are great for introverts and extraverts; they are gatherings where you can find a tribe that shares your quirky pastimes and deep-seated interests. Like Ken Ferazzi says in Never Eat Alone, believe networking is best done with people who love what you love. If you like to lindy hop, watch NFL football, or knit pussy hats, the social settings you share are all networking opportunities.

__ Other:

___________________________________________ 1 2 3 4



Kristin Schuchman, MSW is a career counselor based in Portland, Oregon who works with creative and mission-driven professionals. She writes resumes and coaches individuals seeking support for career indecision, next steps, work re-entry, advancement, and work-life-balance. She offers a free 30-minute Zoom or phone session and presently works with clients remotely. Find out more at

#careertransition #careerchange #careertransitionchecklist #checklist #careerpreparation #homeoffice

bottom of page