Diving in feet first to a whole new journey of self discovery in midlife is definitely challenging, but it can also be incredibly exciting. Think of it as your own personal Indiana Jones adventure but with fewer snakes (hopefully) and a lot more journaling!

In this article, we’ll dish about what it really means to be on a journey of self discovery in midlife. We’ll also touch on some strategies and tools for fully embracing self rediscovery, including my Midlife Reimagined Mastermind workshop.
Table of Contents
What Is a Journey of Self Discovery?
A journey of self discovery can be defined as any process that finds you examining your life, reassessing your needs, and contemplating your fundamental beliefs and values. It’s also about taking actionable steps to lead a life that’s more in tune with what you discover during this process.
Here are some common examples of actions a journey of self discovery might include:
- Reflecting on your life’s journey so far and what it has taught you
- Spending time discovering new passions (or rediscovering old ones)
- Venturing outside of your comfort zone (sometimes willingly, sometimes not so much)
- Building new habits, especially any that support a positive relationship with yourself moving forward
- Connecting or reconnecting with supportive people
- Getting curious about your current self and actively feeding that curiosity
Most people find themselves embarking on a journey of self discovery more than once in life, and with good reason. Major milestones early in life (moving out on your own, getting married, having children – to name just a few examples) naturally prompt us to reconsider who we really are.
The changes midlife brings to the table – like children leaving home, retirement, relationship shifts, milestone birthdays, aging parents, etc. – resurface a lot of these same thoughts for reconsideration.
Midlife also brings a certain solitude to the table that’s perfect for asking ourselves a few questions.
Who am I at this point in my life?
What makes this version of me feel genuinely, crazily joyful…
…and what doesn’t?
When exactly did I accumulate this many shoes I don’t actually wear?
A midlife journey of self discovery is all about finding the answers to questions like these (yes, even the shoe one), taking back the reins, and reclaiming ownership over the gloriously unique story of your life.
Why Is Self Rediscovery Important in Midlife?
Self rediscovery is important in midlife because of the nature of midlife itself.
So many people think this phase of life is about endings when really it’s about transitions, just like so many of the ones you’ve already tackled with excitement, gratitude, and maybe just the tiniest touch of healthy uncertainty in the past.
Moving away from home and starting your new life as a full-fledged adult was scary, but it was exciting and exhilarating, as well, right?
So was the transition from singlehood to married life, from not having children to being a parent, and so on. You made it through all those transitions in one piece and wound up better for it.
Now it’s time to transition again – from the last round of roles you fulfilled into whatever you want your life to be next.
As with other life transitions, embarking on a journey of self-discovery in midlife should start with an honest assessment of your core values as they are today.
Discovering the “why” at the core of your journey of self discovery
I first had the idea to launch The Trybe Women’s Social Club during a similar reassessment and reboot of my own life during the pandemic. Through the process I outline in this article, I determined that my core personal values are:
- Connection with other vibrant, growth-oriented people
- Growth into the best, most productive version of myself through constantly learning and trying new things
- Impact on other women who are also interested in making midlife an exciting, meaningful chapter of their lives
I also read Simon Sinek’s wonderful book, Start with Why, and asked myself some serious questions about my own WHY. That’s when I discovered that my WHY is to push people outside of their comfort zones, open their eyes, and show them a way to live that’s more alive and exciting than they ever thought possible. (Which I do through both my social club and my Midlife Reimagined Mastermind.)
What are your core personal values?
How have you aligned your life with these values over the years as you’ve experienced different life transitions?
What is your WHY?
Unpacking Common Obstacles to Your Ongoing Journey of Self Discovery
Don’t sweat it if you don’t feel giddy with excitement over rediscovering yourself in midlife just yet. You’re only human, and humans can’t help but stumble over a few obstacles (or even their own feet) from time to time.
Here are a few to be on the lookout for:
Fear of change
Figuring out how to rediscover yourself in midlife (and actually taking action) inevitably leads to changes – big changes, more likely than not. Change is scary. It’s scary when you’re young, and it can be even scarier once you’re older.
Unlike the reinvention and self discovery journeys of your youth, there’s no playbook to refer to when you’re not sure whether to hang a left or take a right.
The next phase of your life after the biggies like marriage, parenthood and career is a blank slate that you’re free to fill with whatever you wish.
Scary, I know.
But not as scary as quietly drifting into stagnation instead. Besides, who knows? That big unknown that seems so scary right now might have cookies. They may even be chocolate chip!
Guilt and self-doubt
If you’re like most women, you’ve spent most of your life putting others first. And after decades of living that way, it can be genuinely difficult to finally put yourself first, possibly for the first time ever.
Maybe you feel guilty. Maybe you’re convinced you’re being selfish even thinking about prioritizing yourself.
Let me assure you right now that you’re not.
After a largely selfless life well lived, you absolutely deserve this!
Plus, it’s true what they say about not being able to pour from an empty cup. Taking care of yourself truly is the best way to show up for others. I personally live and breath this mantra and it has served me very well.
Outside expectations
Society has a knack for telling us who we should be and what we should want to do with our lives (especially women). Easing into midlife doesn’t put those expectations to bed, either. You just trade the old ones from your youth in for a brand-new set.
Breaking free from stereotypes and expectations as part of your journey of self-discovery is super worth it, though, and not just for your own inner peace of mind.
The looks on people’s faces when you tell them, “Actually, I’m really into rock climbing and scuba diving right now,” when they ask what you’ve been up to are not to be missed!
How Do I Start the Journey of Self Discovery?
I hope that you’re starting to get pretty excited about learning how to rediscover yourself and diving into the next phase of your life. I’m sure a roadmap of sorts will help, so here are a few practical tips to consider:
Spend some time alone
If you’ve spent most of your life surrounded by other people, spending time in absolute solitude can feel a little strange. (It might feel downright awful. This was very hard for me at first!) However, getting quiet with yourself is one of the most effective ways to get acquainted with the sound of your inner voice and start figuring out what it’s saying to you.
So, begin to explore some enjoyable ways to fall in love with solitude. Meditate, go walking in nature, or lock yourself in your bedroom getting lost in a great book. See what happens.
Rediscover your passions
Once upon a time – way back before you were ever a wife, a mom, a caregiver, or an employee – you had things you were into that brought you joy.
What were they?
What lit you up inside when you were a kid or made you leap out of bed with excitement in the morning as a young person?
Revisit those pastimes and see if they still resonate with you the same way. And yes, it’s totally OK to get really excited about the fact that you can totally afford better supplies at this age!
Try some new things
You’re never too old to try something new or fall madly in love with a new pastime, and your midlife journey of self-discovery is the perfect time for it.
What have you always wanted to try but never had time (or enough money) for before?
Go on a solo trip that involves traveling with purpose. Take up soap making, or competitive dog grooming, or beekeeping, or ghost hunting. (I do 2 of these. Can you guess which 2?)
You never know what you might discover about yourself.
Surround yourself with supportive people
Although solitude definitely has a place in any woman’s journey of self discovery, so does connection. Surround yourself with other women who are grappling with some of the same questions you are. Learn from them while also teaching them what you know.
Consider signing up for an action-oriented self discovery workshop like my Midlife Mastermind Reimagined. You’re guaranteed to make some fantastic new friends, with a healthy dose of radical accountability thrown in for good measure.
Journaling: Your Roadmap for Rediscovering Yourself
Journaling is an incredible tool for self discovery, and it was definitely a huge part of mine. I even used different color pens as a way to notice how my various thoughts and actions related to my newly rediscovered core values – growth, connection & impact.
Whether you’re a lifelong writer or someone who’s never so much as picked up a pen, it’s worth your while to try it, too. You don’t have to write a lot – and it doesn’t even have to make sense. Start with setting a timer for 5 minutes and just letting the ideas flow from your brain out through the pen.
Among other things, you can use journaling to:
- Unpack limiting beliefs
- Clarify new goals
- Celebrate important milestones
- Process complex emotions
Really, anything goes, so choose a journal and some writing tools that speak to you and dive in!
Journaling Prompts for Your Journey of Self Discovery
Not sure where to begin? Try a few of these self rediscovery journaling prompts on for size to start with:
- What moments in my life have shaped who I’ve become?
- What have my biggest challenges taught me about myself?
- How do I feel about my current routine? Is it serving me? What do I want to change about it?
- What legacy do I hope to leave behind?
- What are my greatest strengths?
- How have I grown in the past year? How would I like to grow in the year to come?
- If could live out my own perfect day, what would it look like?
- What activities are so enjoyable they make me lose track of time?
- What limiting beliefs are holding me back?
Again – A journey of self discovery isn’t something you do once or twice when you’re young and then never again. It’s an ongoing journey that lasts your entire life, and you’re far from alone, as millions of other women are going through similar journeys of their own.
So, fall in love with getting to know yourself all over again. Discover what lights you up inside at this age. Share the journey (and maybe even a glass of wine or two) with some like-minded souls. I promise you’ll be glad you did!
I'm Dr. Angela Caveney. I'm a Clinical Psychologist, Neuropsychologist, Founder of The Trybe Women's Social Club and leader of the Midlife Reimagined Mastermind.
If you are interested in learning more about the Mastermind or in creating a community of your own, reach out to me at angela@the-trybe.com to start the conversation.