Unlearning Old Habits: Six Self-Leadership Shifts for Uncertain Times After Fifty
Two emails from Harvard Business Review landed in my inbox this week, summarising Annie Peshkam’s article, To Lead Through Uncertainty, Unlearn Your Assumptions. They were written for senior leaders about unlearning assumptions and building the capacity to lead through uncertainty.
As I read, I wasn’t thinking about CEOs or boardrooms. I was thinking about you, and the women I work with at Flourish After Fifty: women in their fifties and sixties standing at new thresholds.
You might be moving towards an empty nest. You might suddenly find yourself single again or navigating the new identity of becoming a grandparent. You may feel a tug to shift things up at work – change direction, reduce hours, try something new – or be contemplating retirement and realising it raises as many questions as it answers.
These are not small adjustments. They touch identity, belonging, purpose and everyday life. Even the most capable woman can find herself quietly asking, “Who am I now, and what do I want this next chapter to be?” They are indeed times of uncertainty.
Peshkam distinguishes between competence – the skills and experience that help us get things done – and capacity, our ability to stay present and grounded when there are no easy answers.
Most women I meet are already highly competent; this season invites us to grow our capacity to lead ourselves through uncertainty with more honesty, courage and care.
In this blog, I explore Peshkam’s six habits leaders can unlearn in uncertain times and, with a little translation, how they become six self‑leadership shifts for navigating life’s changes after fifty.
1. Unlearn quick fixes; learn to pause
Many of us have spent decades being the “go‑to” person: solving problems quickly, smoothing things over, keeping plates spinning. When life feels uncertain, that habit can show up as rushing for a quick fix just to escape the discomfort.
Sign up for the next thing.
Make a snap decision about work.
Push yourself to “be over it” about adult children moving out, a relationship ending, or a role changing.
The article’s guidance invites leaders to pause rather than leap into action. In your own life, the pause might look like:
Saying quietly, “Right now, I feel sad/lost/restless about this change, and that makes sense.”
Letting yourself not know for a while, rather than forcing an instant answer about “what’s next.”
Giving a transition – like empty nesting or a career shift – time to unfold before locking in big decisions.
💡A reflection to sit with:
Where am I rushing to fix something, when what I really need is space to listen more deeply to myself?
2. Unlearn superficial reassurance; learn to name the difficulty
Another habit the article highlights is calming the room too quickly. In organisations, leaders do it by saying “It will all be fine” before they truly know.
In our personal lives, especially as women, we can do something similar. We tell ourselves, “It’s not that bad, I should be grateful,” even when something feels heavy. We minimise our own struggles because others “have it worse.”
Self-leadership asks for a kinder kind of honesty. It begins when you admit:
“Watching my child leave home is bringing up more than I expected.”
“Becoming single at this age feels frightening and lonely sometimes.”
“I’m excited to be a grandparent, and I’m also working out who I am beyond that role.”
“Part of me is anxious about changing my work, even if it’s what I want.”
Naming the difficulty is not self-pity; it turns private worries into something you can explore, share, and receive support around.`
💡A reflection to sit with:
What am I pretending is “fine” that actually feels heavy, confusing, or unfair?
3. Unlearn carrying burdens alone; learn to share the weight
The author warns against the “hero leader” who tries to carry all the pressure themselves. Their value becomes tied to absorbing stress so others don’t have to.
Many women over fifty know that pattern intimately. You may have spent years being the one who holds everything together – for children, partners, parents, colleagues.
As life changes and responsibilities shift (or stack), carrying everything alone becomes exhausting.
Self-leadership in this season means allowing support. It might look like:
Being more honest with family about what you can and cannot keep doing, especially if you’re caring for both older and younger generations.
Talking with a trusted friend or professional about how you really feel about the empty nest, a breakup, or your evolving role at work.
Joining a circle of women in similar transitions so you don’t have to hold your questions in isolation.
💡A reflection to sit with:
Where could I let someone stand beside me, even 5% more than I do now?
4. Unlearn avoiding conflict; learn to sit with tension
The article encourages leaders not to smooth over disagreements too quickly, but to stay with the tension long enough to understand what each side is afraid of losing.
In this midlife chapter, the tensions may be:
Between your longing for more freedom and your sense of duty to family.
Between how you’ve always been seen (the dependable one, the carer, the worker) and how you want to be seen now.
Between different visions of “what next” in your relationship, around lifestyle, money, location, or retirement timing.
Avoiding conflict can keep the surface calm while resentment or sadness builds underneath. Self-leadership invites you to stay present to the discomfort instead of rushing to make everyone comfortable.
You might ask yourself:
“What am I afraid of losing if I say what I really want here?”
“What might the other person be afraid of losing?”
This kind of curiosity can reveal shared hopes and fears – and new possibilities – that a quick compromise would miss.\
💡A reflection to sit with:
What tension have I been avoiding that actually needs a thoughtful, honest conversation?
5. Unlearn being performative; learn to build deeper connection
The articles talk about leaders trading polish for presence – slowing down, steadying their breath, and being clear about what they know, what they don’t, and what they’re committed to discovering.
Many women in their fifties and sixties have been performing “I’ve got this” for a long time: the competent professional, the organised mother, the reliable partner or friend. The performance can be hard to drop, even when you feel uncertain inside.
Self-leadership now might mean:
Admitting, at least to yourself, “I don’t have all the answers about this next chapter – and that’s OK.”
Letting trusted people see the questions as well as the capabilities.
Showing up as you are – perhaps a little tired, tender, or unsure – instead of who you think you’re supposed to be by now.
You might experiment with saying:
“Here’s what I know. Here’s what I don’t know yet. And here’s what I’m committed to exploring as I navigate this season.”
This kind of grounded honesty often deepens connection – with yourself and with the people who matter most.
💡A reflection to sit with:
Where am I still performing a version of myself that no longer feels true?
6. Unlearn hidden assumptions; relearn how to lead yourself
Finally, the article invites leaders to question assumptions like “certainty equals confidence” and “discomfort equals failure.”
In midlife transitions, many of our hidden assumptions sound like:
“I’m too old to change direction now.”
“It’s selfish to put my needs first when my family still needs me.”
“If I slow down or step back, everything will fall apart.”
“Everyone else seems to be handling this better than I am.”
These scripts often run quietly in the background, shaping how you respond to empty nesting, relationship changes, grandparenting, or career shifts.
Self-leadership is about gently holding these beliefs up to the light and asking, “Is this actually true for me now?” You don’t have to overhaul your life overnight.
You can test small experiments:
Saying yes to one thing that feels aligned with who you’re becoming.
Saying no to one expectation that no longer fits.
Taking one tiny step towards a change you’ve been telling yourself it’s “too late” to consider.
Capacity grows each time you question an old rule and discover that you can survive the discomfort – and maybe even feel more like yourself on the other side.
💡A reflection to sit with:
What’s one old rule about who I’m “allowed” to be that I’m ready to question?
Leading yourself through the uncertainties of this chapter
Although these six shifts were originally offered to help senior leaders navigate complexity at work, I see them as a powerful invitation for all of us, especially as women over fifty, to lead ourselves more compassionately and truthfully through the uncertainties of this time.
🍃You are allowed to pause instead of rushing to fix.
🍃You are allowed to name what is hard.
🍃You are allowed to ask for help and share the weight.
🍃You are allowed to sit with tension and be more real.
🍃You are allowed to seek and build deeper connections.
🍃You are allowed to rewrite assumptions that no longer fit who you are becoming.
💡That is self-leadership in this season of life. And it is how you begin to navigate uncertainty with more spaciousness, self-trust and hope, even when the road ahead is not yet clear.