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Moving On To Your Next Act – 6 Simple Steps For A Remarkable Midlife Transition


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Change Is seldom Easy - Moving On To Your Next Act – 6 Simple Steps For A Remarkable Midlife TransitionUpdated: March 8, 2018

Midlife can be both challenging and exciting as you navigate life changes.

Shedding old roles and taking on new ones, rediscovering forgotten dreams or developing new ambitions, re-energizing your life as you launch a new career or business, may all be a part of your experience.

Learning to slow a life-long fast pace to spend more time doing the things you love, or concentrating on family and friendships you may have neglected are also often areas of focus.

Midlife transitions can be exciting and exhilarating, filling you with fresh energy to pursue new goals, or they can leave you feeling overwhelmed, confused and wondering whether you can meet the new challenges this life stage can bring.

Successfully maneuvering through a midlife transition can be potentially tricky, so in this post we’re talking about simple ways you can help yourself to make that journey a positive and transformative experience in your life.

In this article, we will:

1. Discuss six very basic strategies to help you to enjoy a positive and transformative midlife experience.
2. Examine several common aspects of midlife transition, considering examples that help to illustrate and clarify challenges and/or helpful solutions for dealing with them.
3. Through these identified strategies, leave you with tools you can put into action to help you in effectively addressing your specific midlife situation.

Fortunately, by midlife, unlike your younger years when you faced life with inexperience, (most commonly) limited resources, and less wisdom, you are much better equipped to handle life’s challenges (even if you don’t initially realize it), to emerge stronger, more accomplished and more fulfilled on the other side.

Whether you are changing careers, returning to school for an advanced degree, becoming an empty nester, starting a business, or reinventing yourself, below are a few strategies you can use to ensure a successful midlife transition:

Woman planning for midlife transition1. Plan Plan Plan:

Yeah, I know. It sounds nerdy and geeky, but doing something as simple as developing a plan for your transition will help to make it easier for you to negotiate the inevitable changes you will undergo during the course of your transition process.

Think about it this way…There are lots of things in life we don’t plan out. We often take things as they come.

But then we get to a place in life (midlife crisis anyone?) where all of a sudden, things aren’t what we want or we’re not where we want to be in life and we wonder how in the world THAT happened?

Well, while we may have wanted things to be different, we really didn’t plan for and/or take action for it to be any other way, sooo…you get life by default rather than life by design.

Change almost never comes easily. I’ll say it again…Change almost never comes easily.

But planning for change that is certainly inevitable at midlife, as you pass from one life stage to another, can help to make things go more smoothly than they otherwise might.

Alternately, having no plan can significantly increase your chances of experiencing difficulties, inefficiencies in your process, setbacks and delays, stress and turmoil.

As an example, take the experience of wildly successful comedian/entertainer/radio show host/author/television host/philanthropist Steve Harvey. Steve is a college dropout, and worked at a succession of unfulfilling jobs early in his adult life.

Thirty years ago, while working as an insurance salesman, a friend encouraged Steve to go to an “open mike night” competition at a comedy club in Cleveland, Ohio.

He won the competition and the grand prize of $50 (Woohoo!), and the very next day, without any other forethought or preparation, Steve went in to work and quit his job. At that point, he knew, without any doubt or hesitation, what he wanted to do for the rest of his life.

But Steve’s transition to his newly chosen career and life was anything but smooth. Even though he has a Divine gift for comedy, it took him years to hone his craft and become the enormously successful man we know him to be today.

Those years contained more than a few “hard knocks”, including being homeless for multiple years and living out of his car. This “life season” began at a time when Steve was a few years shy of being considered a bonafide “midlifer”, but still when he was well into adulthood, married and already the father of two children.

Would Mr. Harvey trade the success he enjoys today not to have had those challenges?

I’m pretty sure he wouldn’t. But I’m also just as certain that if there was any other way he could have achieved the level of success he now enjoys without having had to experience the hard and heart-breaking challenges he went through, he would rather have chosen a less difficult journey. (To find out more about Steve and Steve’s journey visit:,,

So, instead of quitting your job outright, immediately making a (blind) leap into a new career or starting a new business, or giving up all you own to live on a deserted island somewhere in the South Pacific, make a plan for your transition.

Creating a plan doesn’t have to slow down your actions or momentum (because you want to act, to DO and not just plan), but creating a “roadmap” for yourself, before you jump into your new life with both feet, can certainly help you to transition more successfully.

Your midlife transition plan could involve, for instance, seeking part time volunteer or internship opportunities in your desired career field.

This would allow you the advantage of obtaining some practical experience, as well as the opportunity to gain a genuine sense of what working in your newly chosen field will be like before going “whole hog” and completely committing yourself to the new endeavor.

Your plan could also involve staying on at your current job while simultaneously working a “side hustle” to save money and build a nest egg to travel the world, or to create and work on building your own business, part time, until it grows large enough to be profitable and generate sufficient revenue to support you.

The key here is to avoid jumping headfirst into a new situation before you have a reasonable safety net to cushion you.

2. Stay Positive:

When faced with new challenges, and especially those that come with midlife transitions, it is important to avoid giving in to fear.

I have always prided myself on being a woman of substance; intelligent, strong, sober-thinking, self-assured, assertive, capable, focused. And armed with those traits, in 2014, I “jumped off a cliff” and initiated my midlife transition.

I voluntarily stepped away from a life I had known for nearly 30 years, and I began a new life and a transition journey that I’m still very much on.

I knew from the beginning that what I was choosing to take on would be a difficult and challenging journey (understatement of the century!), but what I didn’t expect, and what took me by immense surprise was the element of FEAR.

I have always been accustomed to challenges in life; that’s the way my parents raised my two sisters and me.

And from being a little girl who used to climb up into the dark attic of our house, armed only with some gardening gloves, and sitting in the fiberglass insulation, sometimes for hours, trying to catch a bird; being one of only two Black girls on our high school “pom-pom” squad, or choosing a college field of study where I was the only Black student during my entire college career…Oh yeah, I’m used to challenges.

But I never, ever remember actually being afraid. Not until I jumped off that cliff…

And for a short while (read several months), that fear virtually paralyzed me. I didn’t know what to think, where to go next, what I should do, what I wanted to do.

I was frozen. I no longer trusted myself to make decisions, so I didn’t make any, at least not any that amounted to being of any consequence.

Once I “jumped”, I experienced a disconnection from virtually every source of stability and support I had known in my adult life, a disorientation of immense proportion as I no longer felt “anchored”, an identity crisis (if I no longer “belong” to somebody or this group, who am I now?) and so much more.

Out of my personal experience, here’s what I’ve learned about overcoming fear:


1. Always remember that no matter what’s changing in your life or what’s happening around you, you’re still you. At your core, you remain constant and you can trust and believe in yourself.

2. Any decisions you’ve made in the past do not define you and do not have the power to condemn you. It doesn’t matter if your life looks nothing like you originally intended, nor how bad things have been screwed up, or how far “off course” you think you’ve gone. You’re at a different place in your life now than you were when you started, and you have the right and the power to choose differently.

3. If you make a mistake at this point in your decision-making or your actions, so what? At this point in life, you’re playing the game for keeps and you have the right to fumble as many times as it takes to finally get your life on track according to where you are now, where you now want to go and who you now want to be.

4. The most important thing at this stage is to get unstuck. Move on and move in the right direction (“right direction” meaning the one that is in accordance with who and what you are in the “now”), and get your thoughts, your focus, your actions and behavior in alignment with who you are authentically, who you want to be, how you want to manifest your “be-ing”, and how you now want to present yourself to the world.

5. Although the challenge of transition and transformation is real and formidable (change is not an un-scary thing), your fear is something created in your own mind. And because of that fact, you can not only overcome fear, you can learn to use it to your advantage – to propel you forward in a way you might not have otherwise been able to manage or accomplish.

At this stage in life, you have probably faced and overcome tremendous challenges both in your personal life and at work. Draw on the vast inner resources you’ve built up during those times and use them to conquer the challenges you currently face as you navigate your course in midlife.

Seek support in midlife from other women.3. Rally Support:

Chances are, you’re not the only one in your circle of family, friends or acquaintances going through a midlife transition.

As the economy fluctuates and affects businesses and jobs, the condition of our health changes, husbands leave or kids go away to college, you will be hard put to find someone in your inner circle who is not facing some kind of midlife transition.

Start spending quality time with other women. I can’t emphasize this point enough.

Personally, during the course of my life, I haven’t really spent a great deal of time with other women. There are various reasons for that which you don’t have the time for me to go into here, and honestly it’s not that interesting.

But, in spending time with other women, you find that the issues and challenges and even the craziness you may be experiencing is not completely unique to you.

In fact, in general, many of the questions and decisions and issues you face are quite commonly experienced by other women in the same life phase.

And I don’t know about you, but there’s something reassuring in the discovery that you’ve not gone completely mad – That there are others who have experienced what you’re experiencing and lived to tell the tale.

There are two other basic advantages of spending time with women, and reasons you should absolutely do so.

In addition to spending time with women your own age who are in the same midlife phase as are you, you should spend time with older women who can share information, feedback and perspective based on the experience they’ve gained.

You’d be surprised what you glean from a frank conversation with a woman in her 70’s, 80’s or beyond, and it may be a much different conversation than what you’d expect.

Just as importantly, you should spend time with younger women.

Their energy, their ideas, the challenges they face, their experiences in raising young children now all help you to put “you” in perspective in terms of where you are now in life.

But it also helps to keep you connected with what’s current on an experiential level, helps you to continue to think in new and different ways, to consider new and different possibilities, to keep your mind and your view of life “fresh”.

Take the opportunity during this midlife phase to join other like-minded people for ideas and support.

Join a local women’s social or professional group, church group, or support group dedicated to midlife transition, or start a group of your own.

Alternatively, you can join any one of the many online support communities like (yes, I know it’s a shameless plug).

Within these supportive communities, you can discuss issues that affect you including career and job transitions, separation and divorce issues, empty-nest issues, retirement, health changes, shifting roles, caretaking for parents, downsizing, entrepreneurship, relationships and more.

Most often in support groups the subject matter develops from the interests of the members according to what they want to discuss or express.

Such an environment allows you the opportunity to express and share your challenges, feelings and concerns in a safe and supportive way, and receive advice and feedback that is not only relative to your situation, but genuinely helpful and constructive.

You will discover that when you have a group of supportive people to share, spending time with other women in a comfortable, welcoming and supportive environment, whether it’s a formalized support group or simply a group of women you know or would like to get to know, through the sharing of your collective experiences, your experience of midlife change and transformation will go much more easily and less painfully.

You’ll also be putting yourself in position to help others as you are helped. This in turn encourages you, boosts your level of confidence and reminds you of the value of what you have to give to others.

4. Rekindle Old Dreams:

The need to eat, pay a mortgage, retire student loan debt and save for your kids’ college education may have meant that for years you stuck it out in a job that is at best unfulfilling or at worst, you outright hate.

But your circumstances are different now, or you want them to be, and your priorities are changing.

You may have managed to attain some level of financial security, or maybe that’s one of the things on your list to finally achieve.

Whatever the case, it may be time to dust off old dreams that have languished for years on the back burner, or maybe it’s time to create completely new ones and use them to create a new roadmap and a new direction for your life.

Taking yourself through a goal-setting exercise or creating a vision board are two excellent ways of rekindling dreams from earlier in your life, or going through the process of creating new dreams for yourself.

You don’t have to jump in all at once.

Taking small steps towards re-kindling old interests, for example attending an arts class, or taking music lessons or signing up for a couple college courses to rekindle former interests are great ways to explore your options and to decide what directions you now want to take.

Feeding your dreams, even as you transition out of your old life, will give you motivation to move forward, will focus your attention on new goals and will help you to adjust to new changes as you journey into your second act in life.

Women Mentors5. Find A Mentor:

Seeking a mentor doesn’t mean you can’t manage your life, or that you can’t navigate midlife transition on your own.

Most individuals seeking a mentoring relationship are people who find themselves in the midst of a big life change, who desire significant change in their lives, or who may feel “stuck” and in a rut, but are otherwise successful healthy people who need or desire some help and support.

Someone who has successfully been through a midlife transition would make a great mentor, and can help you navigate through this challenging time more easily.

A midlife transition mentor will provide you with the right strategies, act as a sounding board for new ideas, provide a listening year when you are feeling overwhelmed and generally provide the support you need during this process.

A great example of this type relationship was the relationship that existed between Oprah Winfrey and the author, Maya Angelou.

According to Oprah, reading the books of Maya Angelou, whose incredible life story includes a childhood of unimaginable pain and suffering (detailed in the book, I Know Why the Caged Bird Sings), and adulthood of immense experiences, challenges, highs and lows, helped her through early (and at times incredibly painful) periods of her own life.

When Oprah was in her thirties, the two met at a party. From there they formed a deeply personal and enduring friendship that lasted until Maya Angelou’s death in 2014. At that time, Winfrey spoke about their relationship:

“She was there for me always, guiding me through some of the most important years of my life. The world knows her as a poet but at the heart of her, she was a teacher. ‘When you learn, teach. When you get, give’ is one of my best lessons from her.”

“She won three Grammys, spoke six languages and was the second poet in history to recite a poem at a presidential inauguration.”

“She moved through the world with unshakeable calm, confidence and a fierce grace. I loved her and I know she loved me,” she recalled. “I will profoundly miss her. She will always be the rainbow in my clouds.”

(Source: ABC News, Oprah Winfrey Remembers Her Mentor Maya Angelou)

If you decide to choose a mentor, here are some things to keep in mind:

• Decide why you want a mentor. What is it you hope to accomplish through a mentoring relationship that will be beneficial to you. Are you looking for a mentor to help with personal issues, professional or career advice, what?

Do you want a mentor who will offer advice or a different kind of relationship where the mentor acts more as a sound board, or helps you see thing from a new and different perspective, then leaves you to draw your own conclusions, making your decisions from your new-found insights?

Are you looking for someone who is like you in terms of personality type or background, or someone who may have very different experience or perspectives? There are no right or wrong answers here, only clarity for you in determining how a mentoring relationship can be structured and developed to best help you.

• Look for someone you can trust. Trust is a critical element in a successful mentor/mentee relationship.

In addition, search for someone whose life and/or career mirrors key elements of what you desire for yours, and who has demonstrated success in those areas.

A mentor can be a professional acquaintance, a colleague, church leader or spiritual guide, a family elder, or leader in the community.

Relative questions or key elements of consideration for selecting a mentor include whether they have reached a level in their career and profession, spiritual journey or personal life that is similar to where you want to be in yours?

Does this person have the capacity to give you brutally honest (but constructive, helpful and insightful) feedback? Are they “good people”? Are they happy? Do you respect and admire them, and if so, why? Do they enjoy a lifestyle or level of financial security or freedom that you want to also experience?

Successful entrepreneur and multi-millionaire Dani Johnson has a saying, “Find people who have what you want and do what they do.”

• When you ask someone to mentor you, be humble, be kind and be specific. Explain why you want a mentor, what you are looking for in a mentor and your expectations from such a relationship, why you have chosen to ask that person specifically to mentor you. Then give them an opportunity to consider your request and politely decline if it’s something they’re uncomfortable with, or don’t feel for whatever reason would be a good fit. Your end goal here is to find a relationship with someone who can help you to succeed. That means finding a mutually gratifying relationship between yourself and the other person.

Then give them an opportunity to consider your request and politely decline if it’s something they’re uncomfortable with, or don’t feel for whatever reason would be a good fit. Your end goal here is to find a relationship with someone who can help you to succeed. That means finding a mutually gratifying relationship between yourself and the other person.

Your end goal here is to find a relationship with someone who can help you to succeed. That means finding a mutually gratifying relationship between yourself and the other person.

As an alternative to finding a mentor, you may choose to seek out a life coach.

Life coaches are professionals who help people to get “unstuck”.

In their process, they help individuals to deal with specific circumstances and life transitions by accessing current situations, identifying challenges and then determining a course of action which the individual can embark on to create the desired outcome.

Life coaches help individuals through the process of moving forward in their lives, helping them get clarity, set goals that align with their desires and create the lives they want.

Rebecca Perkins, Dr. Barbara Collins and Nancy Sherr are all great examples of professional midlife transition experts, coaches, and authors who specialize in helping women through midlife transition and transformation.

6. Be True To Your Authentic Self:

Most likely at this point in your life, you are done with trying to impress others and conform to societal ideas of success, and the expectations of others about who you are, or how you should behave and live your life.

This is the time for you to pursue dreams that are important to you, choose work that fulfills you based on your genuine interests, your unique characteristics, and skills and abilities you already possess; and reinvent your life – to transform into the person you want the world to see, the one you have always been inside.

Achieving this will most likely not be easy, and oftentimes conflicts with the people around you because you are growing into someone who is different from what they’ve become accustomed to.

Embracing your authenticity may mean tuning out voices that conflict with your inner voice, taking time to think about what you really want and only prioritizing the things that bring you closer to who you really are.

But embracing your authentic self is a necessary and crucial step in your midlife transformation, because it is from that foundation that you will begin to build your new self, your new life, the life that reflects who you are.

I promise you that, in the end, the results of your efforts will have been more than worth the difficult journey. For help in rediscovering your authentic self, follow the link to read the post “52 Truths To Live Life By Design”.

Midlife transition can be a difficult time as you shed old thoughts and perceptions, old behaviors and layers of yourself, to reveal a truer, more authentic you.

When you experience midlife from a position of mindfulness and self-awareness, the resulting transformation can result in a more genuine and deeper existence and experience, filled with meaningful and purposeful work, contribution and other elements that enrich your life.

By employing a few simple strategies, you gain the ability to transition successfully, and come out stronger, better and more fulfilled.

Was this post helpful to you? If so, please let me know in the comments, and then think about who, in your circle of friends, family or just someone you know, that would be encouraged and benefit from this information in their personal journey. Share this post with them. Thanks!


  1. It’s truly amazing what you can do when you develop a positive mindset and surround yourself with loving, supportive people! And oh goodness – planning is totally key! I am a list maker. It always helps me to put things into perspective and create my path. Awesome advice! Thanks so much for sharing Kimberly!

    • Hi Sara! I’m so glad you enjoyed the post! It’s one that I’m passionate about getting out to women who are in the midst of transition and change. Thanks for your wonderful comments and for taking the time to stop by.

      All the Best!

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