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Reentering the Workforce With Ease, Grace and Success

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We are a Chicago- and Atlanta-based coaching and consulting company passionate about facilitating individual, team and organizational change.

We apply cutting-edge, theoretical and practical coaching approaches to help individuals, teams and organizations bring about significant personal and professional transformation.


Many people leave the workforce — by choice or by circumstance. Returning to work after any type of extended absence can be a multi-layered challenge, involving the decision to go back to work, the job search process and the transition back into the workforce. (See Reentering the Workforce: 3 Client Stories, sidebar.)

In our career coaching practice, we frequently work with clients who are either contemplating or actively involved in returning to work after taking considerable time away from their career — as in the case of stay-at-home moms who have taken a leave of ten or more years to raise their family.

Fear is Natural 

One emotion that often accompanies reentering the workforce is fear.

From fear of the unknown to concerns about being “too old,” we know that the transition can be unsettling. Some people express a fear of failure, wondering if they’ll be able to find a decent job, and, once they do, if they’ll be able to perform it well. 

Others are anxious about upsetting others. Moms who return to the workforce are particularly vulnerable to worrying about upsetting the household routine and how their families will fare as a result: “Will the kids be OK if I’m not home when they get off the bus?” “Can I find a job that will allow me the flexibility to attend their after-school basketball games?”

Rejoining the workforce can also spark fears about leaving your comfort zone. As creatures of habit, we tend to become comfortable in our ways. New routines, new people and new ways of doing things can be unnerving.

Being aware of these fears — and addressing them — is essential to a smooth return to the workforce. It often takes a leap of faith to move forward, breaking the cycle of inertia that can cause people to remain stuck. Thinking about going back to work as an adventure can allow you to offset these fears — and to enjoy the ride. 

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Reentering the Workforce: 3 Client Stories

Jill was a 47-year-old stay-at-home mom who had been a successful corporate attorney prior to the birth of her three children. She and her husband decided that she would put her career on hold while their children were young. She enjoyed being able to take “mommy-and-me” classes with them when they were toddlers, and to volunteer as “room parent” when they were in elementary school. As they grew older, Jill remained actively involved in the kids’ day-to-day activities. Once her youngest son entered high school, Jill felt the itch to return to work. But corporate law seemed like another world. Jill wanted to reenter the workforce, but wasn’t sure where she would fit in — or what she wanted to do at this stage of her life.

Bryan had enjoyed a decade-long, lucrative career on the trading floor at the Chicago Mercantile Exchange when he started noticing the toll that the intensity of his job was taking on his health. Around that time, his dad was diagnosed with Alzheimer’s disease. To Bryan, it was a wake-up call: Life is too short to be so stressed. As an only child, he felt that the timing was serendipitous. A comfortable bank account afforded him the luxury of leaving his job to care for his dad for several years until his death. Now, with the well running dry and no family responsibilities to fill his days, Bryan decided it was time to return to work. He knew that trading was no longer an option — but what were his other choices?

Janice was devastated when she was laid off from her job as a vice president at a major clothing retailer. After working for the company for 12 years, a merger rendered her services no longer needed. With a hefty severance package in hand, Janice decided to take the time abroad that she wasn’t able to afford in college. Six months turned into two years … When Janice came home, the idea of jumping back into retail no longer held any appeal. Yet retail was all she knew — or so she thought.



Reentering the Workforce with Ease, Grace and Success

One of the keys to making the entire process more palatable is to temper any negative self-talk, according to Maura Koutoujian, a career and life coach with Jody Michael Associates. “Try to be patient with yourself,” she advises. “Reentering the workforce can be an exciting time in your life if you approach it with curiosity, flexibility and optimism.”

Following are seven strategies that can help you prepare for your return to work:

Overcome obstacles — Your perception can often present the greatest hurdles as you rejoin the workforce. As Maura explains, some factors that you might consider obstacles will serve you better if you can think of them as opportunities. “Thinking that you’re too old to either reenter the workforce or shift careers can be an impediment, but all your years of experience can be what gives you the competitive edge.”

While honoring your circumstances (two kids in college, a physical disability, etc.), try not to let skewed assumptions hinder your prospects. “Hurdles are for jumping over,” as Maura reminds her clients.

Cultivate self-confidence — Both looking for a job and being “the new guy” can be tough for anyone, but if you’ve taken a break from the workforce, your self-confidence might be particularly vulnerable. If your pride has taken a hit due to a layoff or anything else that feels like a rejection, rebuilding your self-confidence is a critical first step in getting back to the workforce. Don’t know where to start? Our Life Catalyst article, Building Self-Confidence: 10 Life-Changing Strategies, can provide you with powerful suggestions.

Keep an open mind — There is no rule that says you have to return to your former job or even industry. Give yourself the space to explore new and unchartered areas. “The ever-changing workplace may require that you adjust your expectations as you head back to work,” Maura says. “In order to try your hand at something new, or even to reintroduce yourself to your former industry, you might find opportunities with a smaller company at first.

“Consulting or freelancing is another way to ease back into work or explore new avenues.” The Mom Project is a Chicago-area startup that matches candidates holding undergraduate degrees and at least five years of work experience with contract opportunities in marketing, sales, project management and more. It’s a great way for stay-at-home moms to dip their toes back into the employment waters, and for companies to find highly qualified talent on a contract basis.

Changes in technology, innovations in service delivery and transformations in the retail world have resulted in the advent of many new career opportunities. While some positions are disappearing or have become obsolete, many more new options have emerged. If you’re overwhelmed by all the choices, or are unsure of which avenue to pursue when reentering the workforce, our Career Discovery process can help you identify your best-fit career based on your aptitudes, interests and values.

Network — Who do you know from your past work life? What organizations have you been — or are you currently — involved in? What skills would you like to learn? All of these questions can help you network your way back to work. (For more networking tips, see Networking: A Valuable Tool for Getting Back to the Workforce, below.)

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Networking: A Valuable Tool for Getting Back to the Workforce

The very thought of networking can be off-putting for many people, but, as Maura points out, it can be one of the best ways to reenter the workforce, particularly if you’re making a career shift.

Many stay-at-home moms haven’t really stayed at home during their break from employment, but have been involved in coordinating the PTO book fair, fundraising for the softball league or teaching English as a Second Language at the local community center. All of these activities have been opportunities not only showcase your skills, but also to expand your network. 

“Some of your strongest skills may not necessarily stand out on your resume, but someone who witnessed you demonstrate them in a volunteer position might be able to make a valuable introduction.”

In addition to taking advantage of online networking, like LinkedIn, Meetups can be a great way to connect with like-minded individuals. You never know when “someone may know someone” who could use a person with your skills to join their team. Professional associations can also offer introductions to helpful networking prospects.

Maura reminds her clients to approach networking with an open mind. Meeting new people provides an opportunity to learn about different companies, stay abreast of industry news and developments, and find out about new roles and positions. It also allows you to practice telling your story and to hone your conversational skills, which will help you prepare for future interviews.



Accept change — The workplace you left five or ten years ago has changed. The digital age has revolutionized many industries and processes. Complaining might be tempting — and even a way to disguise your fears — but it won’t get you very far. In fact, it could hinder your ability to transition back into the workforce. Embrace change and hop on board.

Update your skills — Feeling rusty? Take a Massive Open Online Course (also known as MOOC) through a company such as Alison, which offers programs in project management, healthcare, entrepreneurship and more. If you prefer a more traditional learning environment, your local community college, public library, parks and recreation department or high school district may offer a class that can help you brush up technology-based skills and programs, like Microsoft Office.

Leverage your past — Resist the urge to deem any part of your professional past “a waste” when getting back to the workforce. Rather, view your prior experience as an asset. It may be the very thing that sets you apart from other candidates vying for the same job. If you’re a lawyer but have no desire to return to a career in law, you’re probably really good at deciphering fine print in contracts and a strong negotiator — skills that could help you rise above the competition during the interview process.

Stay-at-home moms returning to work often struggle with ways to find relevance in their experience, yet parenting requires multi-tasking, prioritizing, organizing, coordinating, negotiating and leading — often all at once! 

Getting the Job — and Salary — You Deserve When Returning to the Workforce

reenter workforce Chicago career tips to conquer fears

With a new briefcase in tow, you’re ready to go back to work. But how do you handle explaining gaps in your employment history — and negotiate for the right salary — during the interview process?

1. Be prepared — As with any interview question, being prepared to talk about your employment gap will help you come across as confident. Decide how you want to tell your story, and rehearse it so that it sounds natural during the interview.

2. Tell the truth — Honesty is the best way to approach questions about an employment gap. Keep your responses succinct and avoid editorializing (“my boss was such a jerk,” “that company treated its employees like dirt,” etc.).

3. Don’t apologize — There is no shame in being laid off — or in making a personal decision to leave the workforce. If you regret any decisions that negatively impacted your career path, it’s OK to let your interviewer know that you would likely make a different choice given the opportunity, but leave it at that. This is not the forum for working through any regret you might be feeling.

4. Provide reassurance — When an interviewer asks questions about an employment gap, they’re most likely looking for answers that will make them feel comfortable with both your suitability for the job and your commitment.

5. Be realistic — It’s easy to underestimate your worth after an absence from the workplace. But don’t sell yourself short. Conduct your research using tools like or PayScale to educate yourself about current salary trends in your desired field and geographic area. Also, determine the pay range that you deem acceptable so that you can be clear-sighted in your negotiations. Our Career Catalyst article, The Top 10 Mistakes to Avoid When You Negotiate Salary, can provide you with specific strategies to guide you through the process of discussing compensation.

6. Focus forward — While you owe the interviewer straightforward answers to questions about an employment gap, it’s not necessary to dwell on it. Focus on the contributions you can offer the company and the current position you are discussing. Look forward to your new opportunity — and savor the adventure of this new chapter in your life story. 

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[Jody Michael Associates] leads you to achieve what you believed was impossible. This process can be difficult, but the reward is beautiful.”

-- Zackary A. Prince, Paralegal/Writer
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