When Doing Everything “Right” Still Isn’t Safe
What “55 and Broke” Teaches Us About Systems, Security, and Real Wealth
I was on YouTube one day this week, half listening while I was cooking (I watch a lot of YouTube while cooking!), when a video popped up called “55 and Broke: The Conversation Nobody Wants To Have.”
The creator was someone I had never seen before: Sheila Hammond, from the channel Laugh Lines and Life Lessons.
Within five minutes, I had stopped what I was doing. By the end, I was just standing there, listening to this woman tell the truth in a way that felt both hilarious and 100% real at the same time.
Sheila is talking directly about being laid off in her mid-50s, being out of work for almost two years, and trying to rebuild from a place that does not fit the neat personal finance scripts most of us were raised on.
It is raw, honest, and needed.
I’m going to link the video here because I genuinely think it is worth watching for anyone, at any age, in any income bracket:
Why Sheila’s story hit me
On the surface, Sheila is talking about the myth of “just save 3 to 6 months of expenses,” and you’ll be fine.
Underneath that, she is naming something much bigger.
She did what we are all told to do:
Stayed committed and dedicated to her career for decades
Showed up, performed and overdelivered
Saved for retirement
Tried to be “responsible”
And yet, she still found herself at 55, laid off, with the ground pulled out from under her and no easy way back in.
She is not describing a situation with someone not being good with money; Sheila was describing what happens when you build your whole life around an employment and financial system that quietly changed the rules while you were busy doing your part.
When I say “system” here, I don’t mean some abstract conspiracy. I mean things like:
Companies being able to decide you’re “too expensive” or “not a fit” in your 50s, no matter how solid your performance has been.
Severance and unemployment are designed to cover a short lull, not an 18–24-month significant disruption in income.
A cost of living that has outpaced wages for decades.
Retirement and savings advice that still assumes a smooth run to 65, even though that’s not how many people’s careers and financial realities are positioned for anymore.
That’s the water a lot of us are swimming in, and Sheila was keeping it all the way REAL just naming it out loud from where she’s standing.
This isn’t a “just save more” conversation
Listening to Sheila, I kept thinking about how quickly the world tries to turn her story into a budgeting lecture.
You know the typical soundbites of advice:
“Save more.”
“Plan earlier and better.”
“If you had not spent on this or that.”
It is easy to throw those lines around when you are not the one sitting in the middle of a two-year income gap.
From where I sit, this is not a story about someone who refused to plan. I see it as a story about someone who organized her whole life around a set of rules that were supposed to create safety, and then found out those rules did not hold when the proverbial ground moved.
That context matters.
If we don’t talk about that, we keep telling people to “fix their budget” when the deeper issue is the narratives and games they were taught to trust, which aren’t reliable given the context they understood or believed.
What does this have to do with wealth and business
Most of my work is centred on strategically partnering with women who are growing or reshaping businesses. On paper, it looks like we’re talking about revenue, cash flow, profit, and pricing.
Underneath that, we are almost always talking about how they were taught to create safety inside that same larger system Sheila is bumping up against.
For a lot of us, the story started long before the business was created. Many have narratives playing in the back of their mind, saying:
Be responsible.
Get the good job.
Keep your head down.
Save where you can.
Tap the retirement accounts later.
Do all of that, and you should be safe.
Even though you have left the corporate world and are running your own businesses, that logic often still comes with you.
You can end up building a business that still runs on the same core belief: “If I just keep performing and being ‘good,’ the money will keep me safe.”
Over time, inside that story, it becomes very easy to:
Delay things that actually matter to you
Tolerate conditions in the name of “stability” that quietly drain you
Tell yourself you’ll come back for your health, relationships, or joy “once things calm down”
Not because you don’t care about those things, but because the version of “wealth” you were handed was mostly from a financial lens: income, savings, retirement.
This is why I care so much about our relationship with money – not just the numbers, but:
How we choose to earn
Why we spend and save
What we’re willing to invest in
How we give
The way we lead our money versus letting it lead us
Those patterns can either keep us locked inside the old safety script or help us notice, “something about this is not actually working for the life I want.”
In my world, wealth is not just financial. Money is one lens, not the whole picture.
When you start to see wealth through multiple lenses – your health, relationships, time, capacity, sense of peace – it gets a lot harder to ignore the tradeoffs you’re being asked to make in the name of being “responsible.”
If more of us had been socialized and taught this earlier, I think a lot of us would have:
Advocated for ourselves differently at work before they left
Structured our businesses differently from the start
Made different decisions long before you were forced into a disruption with no runway
That’s part of why Sheila’s story matters so much to me. It shows what happens when the safety path we were sold meets the limits of the system and the real reality of your life.
Remixing life at 50 plus
One of the things I appreciated most about Sheila’s video is that she’s not packaging this as “here is how I turned it all around in 90 days.”
She is telling the truth about being in the middle of it, how she’s rebuilding and not from the glossy “bounce back” narrative, but from the reality of:
Believing that she had more time.”
The transition is much harder than anticipated.
Realizing that all the planning made wasn’t sufficient for the current reality.
There are many women in their 40s, 50s and beyond having to remix their lives in exactly this way:
Leaving or being pushed out of corporate
Starting businesses out of necessity and desire
Redefining what work, money, and wealth need to look like now
Entrepreneurship is not a magical fix.
It does, however, create a different kind of relationship with money and with self. You get to ask:
What do I actually want this to fund?
What does my health need to be like to support me?
What does wealth mean to me beyond always being the person who can pay the bill?
Those are the conversations I want to encourage more of us to have.
Why I am sharing this with you
I’m sharing Sheila’s video and these reflections because I do not think this is just a “50 plus” conversation.
Whether you are 28, 38, 48 or 58, it is worth asking:
Where did I learn what “being responsible with money” looks like?
Am I building my life only around the version of safety I was sold, or around the full version of wealth I actually want?
Where am I trusting systems to stand in the gaps when I can see it most likely won’t?
And on the flip side:
What does wealth look like if I include my health, my relationships, my time, my peace, my ability to rest?
What needs to start shifting now so I’m not forced into a major income disruption later with no say in the timing?
Kudos to Sheila for having the courage to say the quiet parts out loud, with humour and honesty.
I’m grateful her video found its way into my algorithm, and that she’s talking about this from where she is, not from a polished “after” video.
If you watch her video, I hope you let it stretch your thinking a little – not just about savings or retirement, but about the kind of life you’re trying to build and the systems you’re building it inside of.
That’s where the real conversation about wealth starts.
Nechelle, this hit hard. Thank you for surfacing Sheila's story and connecting it to the deeper conversation about what we're actually building toward.
I've been thinking a lot about this lately—how many of us followed the "responsible" playbook perfectly, only to discover the system changed the rules midgame. What gets me is that we're still telling people to "save more" when the real issue is that the safety we were promised was conditional in ways nobody explained upfront.
The part about "what does wealth look like if I include my health, my relationships, my time, my peace" really landed. I think so many of us are exhausting ourselves chasing a version of financial security that requires us to sacrifice everything else that actually makes life worth living.
Your point about entrepreneurship not being a magical fix but creating a different relationship with money and self—yes. It forces you to ask the real questions: What am I actually trying to fund? What does my life need to look like for this to be sustainable?
Going to watch Sheila's video and sit with these questions. Thanks for always bringing the full-picture conversation about wealth, not just the financial piece.
Kudos to Sheila for shedding light on her situation, while she's still in the middle of it, because it's something most of us don't want to even think about because it'll send us spiraling.
And kudos to you for amplifying her story and giving us more context and food for thought because it's something we have to consider, especially as women.
As challenging as it is, a silver lining is that Sheila still has her "health wealth" so she's able to still work and/or build something of her own - imagine if she didn't.
Please keep this convo going because we need more!