Three Steps to Take the Overwhelm Out of a Career Transition

Career transitions don’t start with job boards or recruiters. They start with clarity—about your past, your present, and the impact you want to make next.

A career transition can feel overwhelming. I see this often in the people I work with—and I’ve been through it myself. The big question is: where do you start?

Here are three areas to help you gain clarity and momentum as you navigate your next chapter:

  1. Review Your Work History

Take a step back and look at your journey so far. You don’t have to go all the way back to your first teenage job scooping ice cream—but start far enough back to see the progression of your skills, responsibilities, and impact.

For each role, ask yourself:

  • What position did I hold?
  • What was I responsible for?
  • What knowledge, skills, and abilities did I build?
  • What impact did I make?

Once you’ve listed it all out, analyze the story and reflect on what your career tells you. Did you move from smaller teams to larger ones? Did you shift from technical roles to leadership roles? Did some environments energize you and others drain you? Your history provides valuable clues about what matters most to you.

  1. Define Who You Are Professionally Today

Now that you understand your journey, focus on the present. Who are you today as a professional?

Think of it like an artist’s portfolio. An artist shows their evolution: “I started as a realist, moved into illustration, then explored painting, and here’s where I am today.” You can do the same with your career. Your portfolio is the sum of your skills, experiences, and the unique value you bring.

Ask yourself:

  • How would I describe myself as a professional today?
  • What strengths define me?
  • In what kinds of environments do I thrive?

Clarity here is key—it helps you recognize where you fit best and communicate your value to others.

  1. Identify the Impact You Want to Make Next

Finally, the most important step: What’s the impact you want to make in your next chapter?

Everyone’s answer is different. For example:

  • “I’ve worked in education and loved it, but now I want to build financial security for my family.”
  • “I’ve spent years in big corporations where my contributions felt diluted. Now I want to be part of a smaller team where I can see my impact.”
  • “I’ve always dreamed of starting my own business, now is the time.”

Your impact is your why. It’s the legacy you leave, the contribution you make, and the difference you want to feel.

Your Next Steps

This week, take some time to reflect on these three questions:

  1. What story does your work history tell?
  2. Who are you professionally today?
  3. What impact do you want to make in your next chapter?

Clarity in these areas will give you the confidence to move forward and make your transition with purpose.

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Looking for a New Position: How Can You Determine if You are a Fit?

“I wanted the position so badly; a fortune 50 tech company, working with a highly visible team that was well funded, and they recruited me. I missed some big red flags that I was misaligned with the culture of the organization. What could I have done differently?”

In reality you could have done quite a bit in the search phase. Think of these three areas:

  1. Defining your cultural box
  2. Be a student and educator
  3. Prototyping yourself

Cultural Box

A cultural box sets your boundaries. It defines those areas that are out of alignment with your values. Here is an example. You are competitive, work hard, and put extra time when needed. For you, a boundary is crossed when competition pits team members against each other and becomes cutthroat with team members focused on individual recognition. Now you find yourself in this exact environment. Every day you have a pit in your stomach when you go to work. How do you prevent this from happening?

When you begin your search for a new position, identify and define your values. Those elements that are personally most important to you. In the example, teamwork is a top value. You define it as ensuring success of the team over individual success. Any behavior not fulfilling your definition will be a negative trigger. More frequent or extreme behavior creates more dissonance and misalignment.

Recommendation:

Define your cultural box by taking these two actions:

  • Identify your values and 2) define them with the behavior you expect to have that value fulfilled.

List your top five values with definitions. You now know what you are looking for in an organization.

In your search ask questions, watch behavior, and look for signs of alignment with your values.

Student and Educator

Be a student of the organization and position you are targeting. It takes time to fully understand the details and nuances of an organization and position. Challenge your first impressions. Be a student of what reality is to work every day in that desired position.

Additionally, be an educator to those courting you. Educate them on what makes you a fit and drives your performance. Think of this as dating the organization. In your search do your research about the big organization and the smaller team you will be working with.  Look for opportunities to share and educate your potential new team on what is important to you. It is important they understand the conditions that allow you to contribute and thrive.

Prototyping

This is a concept to test yourself and your assumptions in conversations and experiences. The concept is articulated well in this video by the Stanford Life Design Lab. Have conversations with individuals who are in a similar position or the organization you want to join. In those conversations explore what it would be like to be in their seat. After all they are in the position.

Build a good question bank that will reveal what you are looking for. Then listen and see if you hear your values reflected in the answers.

Here are a few of my favorite questions:

  • How is success measured here?
  • How does this organization develop its people?
  • What does it look like when individuals disagree with the leadership?
  • What have been the reasons for people leaving this organization/team?

Prototype experiences, creating possibilities to test if an organization, team, position, or role is a good fit. Be creative. A prototype experience may take the form of an internship, a half day shadowing a colleague, attending a workshop, eating lunch on site, creating or finding a volunteer opportunity. For some organizations such as hospitals volunteering is easy and provides incredible insights. The goal is to get as close to replicating a position or experience you are pursuing.

Summary

Often when searching for opportunities we focus on “selling” ourselves. We try to convince or show the decision maker how we are the perfect fit. This is a different perspective.

This is understanding the shape of our puzzle piece and deliberately finding where it fits best.

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Career Transition: Nailing Job Applications and Interviews with a Short Timeline

“A close friend of mine just forwarded me a job posting that fits my skill set perfectly. The problem; I have not been actively seeking a change. My resume is not up to date, I have not been networking, and the deadline submission is in two days with interviews in a week. What do I do first?” 

An application process on a short timeline can be overwhelming. To reduce the stress, focus on the priorities. Here is my view of your priorities.

Priority One: Submit an Outstanding Application

The complexity of the application depends on the type of organization and level of the position. The most complex will require an application, cover letter, resume, letters of recommendations, and/or references.

First task, list all the requirements and identify the long lead items such as letters of reference.

Second, analyze the job description and break it apart. Determine how your skills and experiences make you a fit and write them down.

Next, using the above, update your resume tailored for this position. Have someone with credibility review your resume. Consider a review by a professional. An investment of a couple of hundred dollars could be worth thousands in salary and incalculable benefits in emotional wellbeing. A personal recommendation is Scott Vedder. He has assisted dozens of my clients with excellent results.

With the resume complete, the cover letter and other requirements should flow more easily. Why? Because you have completed the challenging thinking of mapping your skills to fit the position.

As you complete the package, update your LinkedIn Profile. Again, the thinking you did on your resume will pay dividends. Ensure your profile is complete prior to hitting “submit” on your application. Undoubtably your package will be compared to your LinkedIn Profile.

What about networking during this phase? The priority is to submit an outstanding application package in a short timeframe. Therefore, any networking should directly support this priority. Network with individuals that can provide insights or beneficial connections. If you have a connection who can help move your package inside the organization, provide insights to the culture of the organization, or specifics of the position, meet with them.

Priority Two: Interview Prep

Package submitted, a sigh of relief. The purpose of your application – get you to the interview phase.

The good work you did in the application phase has laid the foundation for your interview preparation. In this phase you will refine the information and solidify how to communicate it in person.

Add to your initial analysis of the position description an analysis of the mission, vision, and values; Fully understand them and determine how your previous experiences and accomplishments align. Write them down.

Based on your two analysis’ create five 3-minute stories that highlight how you are a fit for the position. I recommend the STAR format. S – Situation, T – Task, A- Action taken, R – Results. Make sure the stories are versatile and can cover elements of the position description, mission, vision, values, and behavioral questions. Behavioral questions are those that start with something like; “Tell me about a time when…” or “How do you…”

Next, practice your stories. At a minimum I recommend identifying a story by a title, identifying what portions of the position description it fits, and writing a couple of bullets for each letter of STAR. Then practice.

Other interview preparation. Google the top 10/25/50/100 interview questions and practice answering them. Put yourself in a realistic setting and have a colleague interview you. There are some interview preparation services available. Think about tapping the alumni services of where you graduated and other recruiting services. For veterans there are services that will provide assistance at no cost. One service that has received excellent reviews by my clients is Candorful. No cost for veterans and an investment of $450 for three practice interviews for non-veterans. Consider the return on investment for this type of service.

Priority Three: Networking

Networking becomes a top priority once you have a comfort level with priorities one and two.

Your networking should focus on “prototyping conversations”. When in a prototyping conversation, in your mind, place yourself into the position of the person you are talking with. Ask questions to help you understand what it would be like to hold that position, work in that organization, or in that industry. Prototype yourself into their role. Focus on the other person and you will be amazed at what you learn about how you may fit into a role.

Short timeline, no problem if you focus and address the requirements in priority order.

Hope this helps.

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Interviewing for Character

“Finally, we found someone who is the perfect fit for our culture.”

“How do you know?”

“In her interview she answered all the questions with what I was looking for.”

Ever have this feeling after interviewing a candidate and then being totally surprised by the actual culture fit after hiring him or her? I have. One person I hired completely snowed me. The suit he wore was never seen again, nor were the values and fit he proclaimed.

How do you truly find out about a candidate’s character. Here are three areas I have found that can reveal a person’s character; their history prior to age 20, relationships, and treatment of the lowest levels in the organization.

History Prior to Age 25

Much of the science around personality that supports our character is mostly formed by the age of 25. So why not explore what a person was like in their early years? Some might say, going down that road is creepy. No way am I bringing up middle school in an interview.

Consider an approach that explores a candidate’s interests. Asking a simple question such as: How have early interests influenced where you are today? You may find influences by mentors such as teachers, coaches, religious leaders, or other associations had a significant impact. I have found individuals readily talk about those influences.

For instance; I interviewed a 32-year-old who grew up with a grandparent who was the victim of a stroke. My interviewee spent a lot of time with his grandfather one-on-one who was nonverbal and in a wheel chair. In his teen years he regularly visited his grandfather without his parents to spend time and often took him on day trips. The same individual continues to work with the special need’s population. What do those experiences tell you about that individual?

How a musician, athlete, student, or community service advocate took on their challenges reveals their character. It is up to you to interpret.

Relationships

What do your relationships say about you and your character.? We spend time with people we enjoy and are often like-minded. We all belong to professional and social organizations outside of the workplace that form our network. Exploring those relationships may provide insights on what is important to the candidate. Maybe more important is how an individual handles close relationship. I have been amazed at what has been revealed in an interview. People have told me about dysfunctional relationships with family members, close friends, and roommates.

My grandmother told me, how someone treats their mother tells you what kind of person they are. Extending that thought to close relationship can be revealing.

Guiding the conversation into these areas is your challenge. However, it easily comes up when talking about life experiences, where someone is from, and interests.

Treatment of Those with No Power

Ever experience an individual berating an airline ticket agent, waitress, or maintenance worker? What were your thoughts of that person’s character?

A practice I adopted for interviews was to ensure each person would wait in my outer office where my administrative assistant was located. My assistant engaged in conversations with every interviewee. That interaction and any interactions on the phone or via email became part of my evaluation of the candidates.

There is the story of Walt Bettinger the CEO of Charles Schwab Corporation, in a business strategy class. The professor gave them a blank sheet of paper for their final exam and said: I’ve taught you everything I can teach you about business in the last 10 weeks, but the most important message, the most important question, is this — What’s the name of the lady who cleans this building?”

How you treat the individuals at the lowest level on the organization chart says more about you than anything else.

What to evaluate if someone is a fit for your organization. Consider exploring the above areas.

Want some insights into how you are thought of; evaluate yourself on the three areas.

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Career Transition – Career Progression: Where do You Start?

Five Checklist Items to Get You Started

Think of your career progression as a series of transitions. In our careers we are constantly looking for what is next. Whether you plan to stay with your current organization long term or move in the near future, building your understanding of what it takes to transition is a worthwhile endeavor.

Here is the starting point I use with clients transitioning, whether it is a promotion, internal change, or jump to a new career field.

My Checklist:

  1. Timeline – how much time do you have until your next transition or progression step?
  2. Number – what is the minimum take home pay required to have the lifestyle you want?
  3. Resume – do you have a resume ready to hand to anyone who asks for it and confident they understand what you can do for them?
  4. LinkedIn – does your LinkedIn profile accurately portray what you have accomplished and where you are going?
  5. Networking – have you developed a systematic networking strategy to support your plan?

There are many facets to a career transition. This checklist provides the basics to get you started.  Let’s look at each item.

Timeline

How much time do you have before you transition to the next position? Being specific about the timeframe is critical in initiating the process. It also puts you in the mindset of controlling the process.

Starting point: Set a target date for being in a new position. The date can be flexible but I recommend keeping it within a quarter.  A goal such as: I will be promoted or have taken an offer by second quarter next year. Why, because it commits you to action and establishes boundaries.

Take out a calendar and do the math

  • Choose a date or date window to be in the new position.
  • Back it up by vacation days and time off prior to starting.
  • What is the day you will walk out of your current position?

Result: You have identified the date you will leave your current position. You now have a timeline.

Number

How much money do you need or want to live your desired lifestyle? Have you done the math?

Determine how your next position impacts the bottom line.

Starting point:

  • Assess your current pay, bonuses, and benefits–what is your take home pay?
  • Consider benefits such as health care, 401k matching, expense accounts, and commuter costs.
  • Construct a proposed budget for your new position taking location into account.

Result: You know your salary and benefit requirements based on location

Resume

How well does your resume represent you in the following two scenarios’?:

  • I meet you at a networking event next week and have no knowledge of your current position. I ask for your resume.
  • A director internal to your company was referred to you as a good candidate for an opening in their division. She asks you for a current resume.

If the above scenarios gave you anything other than complete confidence, your resume is not ready for prime time.

Starting point:

  • Write two resumes; chronological & functional.
  • Get professional resume assistance.
  • Give them to others to review who have experience in your areas of interest.

Result: You have a resume ready to give to anyone who requests it.

LinkedIn

What message does your LinkedIn profile send? Does it accurately portray you and parallel your resume? After you have made a solid effort – get help. LinkedIn should be your professional social media platform of choice.

Starting Point:

  • Use a LinkedIn guide that instructs you how to build an All-Star LinkedIn Profile.
  • Start searching and connecting. Always connect by using a note to introduce yourself.

Result: Your LinkedIn profile will represent you well and potentially attract recruiters or other professionals.

Develop a Networking Strategy

Only 30% of the available job market is advertised, the rest is hidden. Your network is what is going to get you hired. Look to your network to educate you on organizations, people in the fields you are interested in, and the culture of organizations. There are a lot of individuals willing to assist you. Be deliberate and systematic in growing your network.

Starting Point:

  • Start with folks you know; colleagues, friends, and family.
  • Seek out and participate in networking events of all types; job fairs, conferences, virtual meetups, and industry or profession-based events.

Result: You will build a network familiar with you and capable of connecting you to credible contacts in career areas of interest.

This is Just the Beginning

How did you feel about each checklist item? If the list gave you some anxiety, it’s time to get started.

What would be the impact on your transition if today you had every checklist item fully under control? Getting a good start can remove a lot of frustration and build a solid foundation for your transition.

The checklist is just the starting point, there is much more work to be done in your transition.

Looking for a coach to assist you through the transition process? Contact me.

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Military Transition: Where do You Start? Six Checklist Items to Start Your Transition

“My transition snuck up on me, I was not as prepared as I needed to be.”

“The opportunities available to me are incredible, I just needed a methodology to find them.”

“The Transition Assistance Program was valuable but I did it too late.”

“The difference my tax-free allowances made in my pay compared to the civilian world was eye-opening.”

“I put hours into my resume, I never thought I would need six resumes.”

“I have grown so much through the transition process.”

“Where is the one-stop guide to transitioning?”

“Getting all my medical issues documented took a lot of effort.”

Everyone transitions out of the military – everyone. It is a process not an event and it takes preparation. Just as you prepared for your transition into the service, you have to do the same getting out. When I coach veterans on a career transition this checklist is my starting point.

My Checklist:
1. Runway – how much time do you have until your active duty expires and you need to be generating income
2. Number – what is the minimum take-home pay required to have the lifestyle you want
3. Resume – do you have a resume to hand anyone not familiar with the military and be confident they understand what you can do for them
4. LinkedIn – does your LinkedIn profile accurately portray, parallel your resume, and send the message you want
5. Medical – are all your medical injuries accurately documented in your medical record
6. Veterans Administration Claim – are you connected with a Veteran Service Organization (VSO) representative to assist you with submitting your VA claim

Getting out can be overwhelming. If you are separating in 8 days or 18 months from today, you will address each item above in a very personal way. A proactive approach started months in advance will smooth out the process.

Let’s get started by focusing on the basics.

Runway
How much time do you have before you are separated from the service?

Takeoff is more than being out of the service, to me it also means generating income. I have seen the gamut. There are individuals wanting to “double dip” and be earning income while on terminal leave and others with no intention of pursuing a job. They choose to live off of their retirement and/or disability.

Starting point: What is your end of active service date and what is your target date for earning income? Take out a calendar and do the math for both.

  • Choose your end of service date
  • Back it up by the terminal leave you will be taking
  • Add the Permissive TAD you will take (different for retiring and separating members)
  • Add any internship Permissive TAD days.

The date you stop working in your current role could be 6-9 months prior to separation. It depends on the leave you have saved, whether you are retiring or separating, and if you participate in an internship.

Number
How much money do you need to live? Have you done the math?

Are you happy with the lifestyle your current income provides? Do you know what that same income is worth in the outside world? There are significant tax advantages incorporated into your military allowances and specialty pay. Here are a couple of resources to start your research:
https://www.military.com/benefits/military-pay/calculator
https://www.financialfrontline.org/civilian-pay-to-equal-military-take-home-pay/

Starting point:

  • Assess your current pay, allowances, and specialty pay – what is your take home pay?
  • Convert your non-taxable income into taxable income – what is your take home pay?
  • Construct a budget for your current location and your proposed location.
  • What is the number your new budget tells you need to maintain your lifestyle?

Resume
Suppose I met you at a networking event and had no knowledge of the military. If I asked you for your resume, how well will it represent you? If that question gave you anything other than complete confidence, your resume is not ready for prime time.

Starting point:

  • Get professional resume assistance from at least one organization that assists veterans. Some are free and some charge.
  • Write a chronological listing of all the jobs you have had
  • Write a list of your top five skills and how you demonstrated them
  • Write a functional resume to show what you bring to your next organization
  • Give it to others with no military background for review
  • Give it to others with no military background for review
  • Give it to others with no military background for review

LinkedIn
What is the message your LinkedIn profile sends? Does it accurately portray and parallel your resume? Just like your resume, it requires demilitarization which is very difficult for many of us. After you have made a solid effort – get help. LinkedIn should be your professional social media platform of choice.

Starting Point:

  • Use a LinkedIn guide that instructs you how to build an All-Star LinkedIn Profile
  • Confirm your profile parallels your resume
  • Have a professional “civilian” photo
  • Join LinkedIn Premium at zero cost for one year (veteran benefit)
  • Start searching and connecting. Always connect by using a note to introduce yourself

Medical
How accurate is your medical record? How well does it document all of your medical injuries or issues? This is the time to get your medical record in order. Ensure your record accurately documents your medical history. The medical process can be time consuming. Do not delay in getting this started.

Starting Point:

  • Review your record for completeness
  • Make appointments for those items you have pushed off
  • Schedule your final physical, usually 180 days prior to separation

Veterans Administration Claim
The medical item above flow right into your VA Claim. It is helpful to find a colleague who is 6-9 months ahead of you in the transition process. They will readily share their personal experiences with the process. A key area is how they worked with their Veteran Support Organization (VSO) representative.

Starting Point:

  • Seek out local VSO representatives
  • Have your medical record in good shape by 180 days prior to separation
  • Work with your VSO representative to complete your VA claim
  • Schedule your VA appointments as soon as possible

How did you feel about each checklist item? If the list gave you some anxiety, it’s time to get started.

What would be the impact on your transition if you had every checklist item fully under control at this point? I have seen veterans in transition move from near panic to being calm and deliberate – because the checklist gave them direction.

The checklist is just the starting point, there is much more work to be done in your transition.

Looking for a coach to assist you through the transitions process? Contact me.

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Career Transition Coaching: ROI Case – The Unhappy Professional

Jeremy 42 is a managing partner in a professional services firm and has been with them for 10 years. He is a steady performer doing well financially (200k+) depending on the year and settled into a niche part of the business as an expert. He is well respected by everyone in the firm and a key part of the management team. With two children, ages 9 and 7 he wants to be able to spend more time around them particularly at their sporting and school events. One goal he has is to coach soccer for his kids as he played in college. His commute is making that impossible since he spends a minimum of 2 hours a day commuting which often turns into 3 hours.

The work is not all that exciting since he has become the firm’s “expert” in a particular area. There are plenty of challenges such as meeting deadlines, creating deliverables, modifying contracts, and developing junior associates. For him work has become fairly routine. He could branch into other areas if he wanted, however, has not taken the time and effort to build an additional book of business. He has become very comfortable with his current situation.

He came to me looking for assistance in determining where to start with his search and how to go about it. Some requirements were that he had to keep his salary at the current level, reduce time on the road, have significant vacation time, and be in a position of leadership.

We started with sharpening the elements of his vision for the perfect position. He determined his desire to move was based more on family lifestyle than work. Spending time with the family became the primary driver rather than professional responsibilities. That did present some challenges as leadership roles are what commanded the salary, he was familiar with and looking for.

Examining his skill set he was very clear that business development and networking were not his strong suit. It was also clear that his expertise forced clients and colleagues to see him as one dimensional. Most of his current book of business was referred to him from previous clients or colleagues in the firm. He was capable of a broad range in his field however, his recent experience did not reflect that capability. He also wanted to keep his search confidential.

Actions

The first actions were to determine how to search what the potential market was for him. We started by having Jeremy identify potential firms and individuals that might be able to assist him in answering that question. That meant working on his networking skills. We worked on what networking was for him. He came up with a definition that translated into small meetings, presentations, coffees or lunches with colleagues. He explored other firms made connections and even applied and interviewed for several positions.

The Results

What Jeremy discovered was that changing firms would cost him significantly in salary. He was not going to be brought in as a managing partner. He would have to start as an associate and build up to partner. That was disappointing.

He also found that he was actually pretty good at networking, using his style. Renewing previous relationships, creating new ones, and building on his reputation as an expert proved beneficial. One result was that it brought some new business in his area of expertise.

He also examined going into business for himself, which after doing the research he determined would take up more time than his current situation. Nope going to hang out his own shingle.

Looking at where he was gaining traction, he made the decision to go to the management team and make a proposal. He proposed that he work from home at least two days a week with the potential for more if he cultivated clients in his geographic area. The management team accepted his proposal with a plan to implement it in increments to ensure it did not have a negative impact on business and development of junior associates.

Today

Jeremy is working from home approximately two and a half days a week. He has improved his book of business and gained a couple of clients in the area where he lives. He has adopted a business development approach based on his networking strategy. As an assistant soccer coach, he participates with his children’s teams several times a week.

Jeremy is much happier in his current arrangement. He is still focused on his vision of being a well-paid executive with time to live the lifestyle he wanted. He did not change firms however; he did transition his career to be focused on what is most important to him. Jeremy is controlling his career.

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Career Transition Coaching

 

Invest in Yourself With Career Transition Coaching

If you could invest 8 hours and less than one day’s pay to set you on the path to your ideal career, would you do it?

Yes? Then you are ready to invest in career transition coaching. Transition coaching is not just for career changes. It helps you develop clarity in your current career and life.  It can help you to earn that promotion you deserve, define your path forward, establish better work/life balance, or make that change you are contemplating. 

Many professionals are following the career advice of others; family, friends, colleagues, or mentors. Why? Because they have not invested in themselves to create a clear vision of their future.

Differentiate yourself. Take the time to assess what is most important in your personal and professional life. Career Transition Coaching  provides the time and space to:

  • Develop clarity in defining your vision
  • Align your vision with what is most important to you
  • Embark on the journey to realize your vision

Contact me for a complementary consultation and get started on building your ideal future.

 

 

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