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          11/13/2025

          2:45pm - 4:00pm

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          City Awake empowers young professionals in a variety of ways that encourages these rising leaders to stay invested in the region’s future success.

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          Our Boston’s Future Leaders (BFL) program provides emerging leaders with a socially conscious and civically engaged leadership toolkit, as well as the opportunity to apply their knowledge through experiential assignments.

          Read More
          Massachusetts Apprentice Network

          The Massachusetts Apprentice Network convenes employers, training providers, and talent sources interested in developing and implementing apprenticeship programs in occupations across industries and statewide in fields such as tech, advanced manufacturing, healthcare, financial services, and more.

          Read More
          Strategic Communication for Better Collaboration

          Level up your leadership and communication in this Boston Chamber workshop for professionals—gain essential skills in team alignment.

          Read More
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Five Tips to Successfully Relaunch Your Career

November 5, 2021

In 2001, after fifteen years of staying home to raise my three children, I knew it was time for me to step back into the workforce. Reentering felt overwhelming, which many of you can relate to especially now with the additional challenges of COVID. As a single mom, I had been juggling what was best for my kids, while also keeping my skills sharp through various volunteer roles and, at one point, working part-time as a gourmet and specialty food sales rep. I knew I would return to my career full-time at some point. But much had changed in the workforce since I had been a product manager at a top ten bank in the U.S. right after college. In order to relaunch my career, I knew it was critical to identify, articulate, and hone my business skills—as well as reach out to friends for input.

One aspect of the business environment that hadn’t changed and never will is the importance of relationships. As my career has advanced over these past 20 years, I attribute my successes and sense of satisfaction to the variety of business contacts and a few key mentors who have been with me each step of the way. My network has grown exponentially over time, and I encourage you to establish and maintain your relationships—they are the foundation of career success. In fact, my four most recent roles at companies since reentering the workforce were thanks to introductions by contacts and friends.

As my career has advanced over these past 20 years, I attribute my successes and sense of satisfaction to the variety of business contacts and a few key mentors who have been with me each step of the way. My network has grown exponentially over time, and I encourage you to establish and maintain your relationships.

In addition to relationships, I also thought about what made me unique, and identified the skills I could bring to a company to help them further their goals. Everyone has a myriad of life experiences—some we’d like to remember and others we’d rather forget. When you pause and reflect on this, you’ll realize that your life experiences and your professional skillset make you—YOU. This all contributes to your tenacity, grit, creativity, wisdom, and common sense. These insights can also help you focus on a career direction that is fulfilling both personally and professionally.

But where to begin when you’re ready to step back into your career? Here are some things to keep in mind that were especially helpful to me as I relaunched my career and have continued to grow professionally.

Everyone has a myriad of life experiences—some we’d like to remember and others we’d rather forget. When you pause and reflect on this, you’ll realize that your life experiences and your professional skillset make you—YOU.

1. Your Skillset

What skills did you use before you left the workforce? Of those, which did you enjoy spending time on and didn’t feel like work? What do you know you absolutely don’t want to do again?

2. Your Differentiators 

Since leaving the workforce, what have you spent time doing—and most importantly what skills have differentiated you and made you successful in your endeavors? Obviously, a volunteer/leadership role requires skills that are transferable to your career, but also think about those experiences that are less obvious, which have also helped you develop applicable skills.

3. Roles and Where You Fit In

What roles require these skills? Which companies have a culture where you will be valued and fit in both personally and professionally? Thinking about this will help you narrow the overwhelming number of directions you might turn. Make a list. Don’t be afraid to reach out to companies. My first job when I re-entered the workforce was thanks to an article I read about a branding and design firm that was growing. I reached out to that firm and pitched them my skills. They had been considering hiring someone, and they hired me.

4. Get Involved and be a Connector

Relationships are critical to success and personal satisfaction. Always be a “giver.” Offer to help others with introductions to people who might be beneficial for them to know. Join organizations and attend industry events. Stay in touch with people and learn from them. You’ll look back and appreciate your business relationships as well as the deeper friendships that often develop.

5. Stay Organized and Focused 

Keep a spreadsheet with all the details of your career outreach efforts including your target list and dates. Be focused and strategic. Your spreadsheet will make it easy to know when to circle back with someone and you can also easily track your progress.

Begin with the end in mind, which Steven Covey discusses in The 7 Habits of Highly Effective People. What type of role do you see yourself in, what skills does it require and how have you demonstrated that you already have those skills from all your experiences?

You are unique. Think about reentering the workforce as an opportunity to contribute your skills, which is why your first steps should be to identify those skills and what you truly enjoy doing. Then, reach out to your network for support. As I look back on my career, I most value my relationships with friends and mentors. They not only helped me relaunch and advance my career, but they have also introduced me to ideas, perspectives, and people that have shaped my life.

Kappy Freund is a Principal and Head of Marketing at DGC (DiCicco, Gulman & Company), an accounting and business advisory firm specializing in services for businesses and high-net worth individuals. DGC’s team of over 200 collaborates with clients and their advisors to understand objectives and position clients for the future. When not focusing on marketing and business development, Kappy enjoys mentoring and coaching people on their careers.

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