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RE:WORK FIELD GUIDE · UPDATED SEPTEMBER 25, 2026

Finding jobs in Chicago when your experience takes a different path.

Your background may not look like the example in a job posting. A useful search starts with understanding which requirements matter, where your experience transfers, and what you can demonstrate next.

01 / PUT IT INTO PRACTICE

Start with current openings and real requirements.

This is a job-search and training guide, not a list of employers currently hiring. Check an employer’s own careers page to confirm that an opening is still available before applying.

Compare several postings for the same kind of role. Separate essential requirements from preferences, and look for duties you have performed in another setting. A degree may be required for one role and optional for another; do not assume that every employer treats experience the same way.

02 / PUT IT INTO PRACTICE

Make transferable experience visible.

01

Customer-facing work

Serving customers can provide examples of listening, explaining options, resolving problems, and staying reliable under pressure.

02

Organization and coordination

Scheduling, tracking details, managing competing needs, or coordinating a group can demonstrate planning and follow-through.

03

Learning and initiative

Describe how you learned a process, asked for feedback, practiced, or solved a problem. Use specific actions and observable results.

A past task is not automatically equivalent to a new role. Explain the connection clearly and be honest about what you still need to learn.

03 / PUT IT INTO PRACTICE

Build a search you can sustain.

  1. Choose a manageable set of roles and employers to research.
  2. Tailor your application around relevant, truthful evidence.
  3. Prepare a thoughtful question for someone who understands the work.
  4. Track each opportunity, conversation, and next step.
  5. Review what produces useful information and adjust.

You can apply while building relationships. A referral is not a prerequisite, and nobody should be pressured to provide one.

04 / PUT IT INTO PRACTICE

Get support without a tuition bill.

re:WORK TRAINING is based in Chicago and serves learners across the U.S. The free Academy uses sales strategy to teach career-search skills and professional relationship-building. Many participants pursue sales; the approach can support other paths too.

Explore our Chicago job-training page for the two ways to learn, participant stories, and current next steps.

FREE LEARNING · COMMUNITY SUPPORT

Put the approach into practice.

01

Start at your own pace.

The free Go To Market Career Academy is available in MissionXP now. Complete lessons and practical missions on your schedule, with community support. Start the self-paced Academy.

02

Learn with a quarterly cohort.

Express interest in an eight-week re:WORK cohort with structured instruction, coaching, and peer learning. Staff confirm placement and schedules; participation is free. Register cohort interest.

You can begin self-paced learning while exploring a cohort. Commitment to the process may support cohort consideration; a place is not automatic. Employment, introductions, and referrals are not guaranteed.

YOUR NEXT STEP

Build the strategy behind your next move.

Learn how to research opportunities, communicate your value, build professional relationships, and follow through.

KEEP EXPLORING

More ideas for your next step.

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