Second Wind: Building A Team To Help You Cross Over To A Great Career

As the early morning sun peeked up through the dark sky, her running shoes hit the pavement. Full of energy and excitement, she embraced the cold brisk air and began her daily four-mile run. Forty-five minutes later, she began losing steam, but the end of the road was in sight. She remembered her training and how to gain a second wind. As an adrenaline boost set in, she ran hard, crossing over the invisible finish line. Whether physical or psychological in nature, professional runners are trained to catch their second wind and find the strength to keep going. Even better, runners can harness this energy to make it to the finish line without the assistance of others. Career-seekers cannot. In the final stages of your career change, you may feel tired or too exhausted to move forward and you’ll need solid partners to help you get through the tough days ahead.

In essence, you will need to tap into your own second wind, with the help of a team of individuals who can provide the “wind” beneath your wings. This necessary and powerful support system will keep you moving in the right direction until you have achieved your career-change goal. We recommend that you choose four different partners who will look at your change from different perspectives—Winner, Igniter, Naysayer, and Dreamer (WIND)—keep your energy strong, and challenge your thinking.

So, how do you assemble a second WIND career transition team? Let’s look at each of these roles more closely so you can choose the best possible candidates.

Assemble A Team

During times of career uncertainty, many people keep their career searches a secret. But don’t make the same mistake and go at it alone. Instead, use your friends and family to support you through the process. By viewing your career search decisions through different lenses and from multiple angles, you’ll be better poised to make an objective, informed decision. As you read through the following definitions for the four members of your career transition team, think about the people you trust in your network and what style, characteristics, and personality they naturally lean toward. Each of the individuals from the Second Wind Transition team will play a critical role in providing you with valuable insight when evaluating your next career move.

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Identify Your Second WIND Transition Team

While networking is important for any job seeker, building a career transition team is critical, as these are the trusted people who will guide you through the entire process. Comprised of friends, family, or past and present colleagues—or all of the above—your career transition team provides you with four distinct components of support. Ideally, you will identify a different point person for each of the following:

Winner: A winner is an optimistic, highly competitive person who will assist you in putting together a strong execution plan to win. An ideal winner is typically a current or former boss, a work colleague, or a professional peer—someone who knows your work skills the best and has seen you up-close in action, This WIND team member will advise you on your special skills and talents, help illuminate your capabilities, and help you see the linkages from your current skills to your identified transferrable skills.

Igniter: An igniter is a friend who will push you when you are running out of steam. A “spiritual guide” of sorts, this is someone with whom you feel comfortable praying or, if you are not a religious person, they will be the one providing you with well wishes. While he or she is far removed from your work field and doesn’t necessarily understand your work skill sets, an igniter knows who you are on a personal level. Their role isn’t to judge whether or not you could do the new job—it is to lift you up when you’re feeling down. Igniters believe in you as an individual and act as your own personal cheerleader.

Naysayer: A naysayer is a person who can be candid with you and tell you what you may not want to hear. Their primary role is to judge your progress and they won’t let up until your mission is accomplished. Being a naysayer is not for the faint of heart—he or she must be willing to be direct, point out the negative aspects of possible opportunities, and help you think through the risks associated with your change.

Dreamer: A dreamer is someone who knows the broader aspect of your career field and can give you guidance on how the hiring process works. A role often filled by an HR person, mentor, career coach, or executive recruiter, a dreamer helps you dream about the possibilities and the various opportunities available to you, as well as the myriad of career paths/bridges you can take to get there. Once you’ve honed in on possible options, a dreamer may even help prep you for your interviews.

Try choosing a different person for each of these roles. If that’s not possible, ensure that no one person fulfills more than two, especially if this person is a best friend or a spouse, as you may overburden them and place the relationship at risk. This is a highly sensitive time for your closest friends and family as well, so take care that you are not setting them up for failure in their role of supporting you. To do this, tell these key people which roles you want them to play upfront and ask them to stick to those roles throughout your transition unless you have specifically asked them to formally change roles.

Remember—your career transition team is essential to activating your job search. This team of individuals provides the mental and physical wind beneath your wings. Your Second WIND Transition Team is a powerful support system that, once in place, will keep you moving in the right direction until you have reached your career change goal.

Who will be on your Second WIND Transition Team? Indicate Below.

W ________________




Engage Your Second WIND Transition Team

How do you engage your transition team?

The four key people you have chosen to support you through this change can help you keep your momentum and make informed decisions. Here are a few strategies for best engaging with your team.

Conversation Starters

Because getting support means sharing your hopes, goals, and insecurities with others, it can be difficult to ask for the help you need. Below are some conversation starters to help you begin communication with your team:


  • You’ve been able to see me perform at my best and I’d like to get your thoughts about…
  • I value the feedback you’ve given me in the past and I wonder what you think about…
  • Would you be willing to help me explore my strength and capabilities to do…


  • What do you think about me becoming a (insert your chosen field)…
  • I’d like to capture your thoughts about me finding a new career in…
  • Would you be willing to support me on my journey to become a (insert your chosen field)…


  • You bring a unique point of view and I’d like you to challenge my thinking about…
  • I value how direct and honest you have been with me and I wonder if you can…
  • Would you be willing to play devil’s advocate as I research and pursue new opportunities in…


  • I am hoping I could borrow your expertise about…
  • I am thinking of making a change and I’d like to pick your brain about…
  • Would you be willing to help me discover which roles best match my skills and interests in…

Reactions You Can Expect and How to Respond

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Rules of Engagement Dos and Don’ts

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Change can be difficult, but you don’t have to do it alone. This informal team can help you to cross over to a great career.

About Monica…

Monica Sauls is a founder of CCLT and a corporate human resources leader with expertise in talent management, career development, change management, training, and organization development. In her additional time she writes, delivers speaking engagements, and coaches professionals—from entry-level employees to executives—to thrive from one stage of their careers to another. For more information about Monica, please visit