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Midlife Career Crossroads

We’re back again with another insightful career conversation.

How did you like our last post on midlife career transitions? If you have not read it yet, please click the button below to read and share.

Now that you have read Midlife Career Transitions, let’s continue. This week, we bring you Midlife Career Crossroads.

On your career journey, when you arrive at the career crossroads, this is the time to make the critical decision that will shape the face and future of your career. The crossroad is a place of intersection of two or more roads leading you Northward, Eastward or Westward. The directions run transversely, requiring you to take a directional decision based on the insight available to you. It is a junction situation or point in time when a critical decision must be made while excluding other options.

Do you remember our quote?

“Your life must be to get up and go to play at what you call work. Have a calling for what you do and pursue this work as a personal calling.”

If your job is taking away your authenticity, peace, time, happiness, talents and you are becoming someone or “something” else, it is time to ask yourself deeper questions. If you are constantly asking yourself - “what am I doing here ?” then it is time to ask yourself - is this my “calling” or a great means to my calling?.

What do you do then?

If you have self-anchoring tools such as: the revalidation of your personal values as a person, your mission and vision statement, your long term goals, deep aspirations, your dreams and a clear description of who you have defined yourself to be - Then this is a great time to stop, read and recite these anchoring statements to yourself - this is the time to check-in with yourself and ensure you are going and growing in the right or preferred direction. If you do not have these tools, then you ought to create them now.

You can also - Ask yourself the 5 basic career checkpoint questions: How can I showcase my authentic self and then blossom?

  1. What do I have passion for - what do I really want to do - what are my short and long term careers?

  2. What makes me happy - what are my realistic career expectations - what pays the bills - What is realistic within my circumstance for now and for how long?

  3. What is/are my talent(s) - where can I showcase these talents?

  4. What are my top skills - where are these skills valued and rewarded?

  5. Where am I going - where is my work-career and work-life leading me?

If your career does not align with your answers, you will arrive at a career crossroad.

You can contact me to have a free coaching session on career crossroads - using the crossroad tools (details are at the end of this post).

One of the crossroads you may arrive at is between the path of a job change or a career transition. Another crossroad is between the path ‘to relocate’ or ‘not to relocate.’ To change department or function or take up the promotion offer that will change the functions and scope of work leading to another path.

We will examine the “Japa” crossroad in another post; let’s focus on job change and career transition today.

In our previous post, we mentioned that a job change differs from a career transition. How?

A job change is an easy and straightforward process where you take another job within the same job family or job definition and similar job description, same industry. For instance, you move from working as an accountant to working as a financial controller or financial strategist; still within the same profession and within a similar work organization.

On the other hand, a career transition is a functional change in job definition, job description, and job focus across industries or professions. For instance, you move from working as an accountant to working as a teacher or writer.

The career transition may also be occasioned by promotion from the mid level role into the management position.

What do you do when you get to these crossroads?

Midlife Encounters - The Career Decision

Do you turn back to where you came from? (remain in the same career path even though you are totally dissatisfied).

How do you deal with all the issues around the family routines, responsibilities and current personal stability or security.

How do you make a choice between a job change or a full-on career transition -can you achieve both and not compromise on your personal stability?

- Through your answers to the 5 career checkpoint questions.

If your answers do not align with your job industry, you may need a career transition. If they align with your industry and not with your job role, then you may need a job change.

Navigating your way through career crossroads is very important because your career has great impact on:

  1. Your spiritual goals and development.

  2. Your location and travel time.

  3. Your health, personal vision, vitality and food habits.

  4. Your finances (purchasing power and saving ability).

  5. Your social life, romantic life, networking ability, and relationship development.

  6. Your attitude/mindset and view of life.

  7. Your family life, engagement, and culture.

  8. Your hobbies, interests, and leisure time.

“When you are on the right career path, you find fulfillment because you are not working to get paid, you are doing what you love and creating value then the payment finds you.”

Career transition at midlife requires planning and better understanding of the voyage. The dynamics at this stage needs better comprehension and more stakeholders in the planning and execution process.

  • Decide on the new career you want to build and highlight what is required to help you become successful in the new career.

  • Determine the trade-offs you need to make and how long it will take you to recover.

  • Determine the support you will need from family and friends as you go through the transition, and it is important to share your long term plans with those supporting you, as this will help them appreciate what is involved in the change process.

Take courage and begin your transition journey today; it is simply a midlife encounter that you can navigate smoothly with adequate planning and knowledge.



The Midlife Encounters Book Series

Encounter 1: Rainbow Experience

Coming Soon


Article by:

OyeStir (The Midlife Coach)



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Adekunbi Grillo
Adekunbi Grillo
Oct 17, 2022

Thank you so much for this very helpful resource. It helps give clarity for some of my grey areas. I'm currently building and rebuilding 2 different businesses and I've stumbled in and camped at some crossroads...I am definitely keeping this article to use as a constant reference. You are such a blessing sir.

Dec 13, 2022
Replying to

We are so glad this helped you. We hope you are able to rebuild the businesses successfully.

You can also book one of our career coaching sessions by sending us a mail at or call/send us a chat at +2349060370862

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