Written in 2014, on the first anniversary of my father’s death.
One year ago today, my father died. It was one of those moments that wasn’t exactly unexpected, and was still one of the most difficult. It was also one of the biggest turning points in my life.
So many things have changed in the year since. I took the opportunity handed to me and decided to run with it. Out of grief and sorrow, I decided to follow what I wanted to do at full speed.
The results have been startling. Shortly after he died, I left a steady, well-paying job of almost seven years to go in an entirely different direction. Out of technology, IT and software engineering, and into senior care. A very different way of life — helping people at a point where they need an extra hand with the ordinary business of living, rather than building the next new widget. Helping people who are genuinely vulnerable.
I spent almost the entire year working his estate through probate while starting two companies and keeping another couple going.
Starting two simultaneously sounded like a reasonable idea at the time, if a little on the crazy side. It was probably the smartest and the stupidest thing I’ve done. Two companies means twice the work, twice the frustration, twice the accounting and payroll and the grind of getting anything off the ground. Twice as many people to hire, and about half the sleep.
Yet here I am at the one-year mark for both, and we’re well on the way to profitability. It has taken a great deal of work and persistence. I’m fairly sure most people thought it wasn’t possible. It is possible. It just isn’t easy.
I’ve spent a lot of this year missing him. I’ve also thanked him for nudging me toward what I feel called to do, and for the reminder that life can be short and we don’t get much say in it. He had Parkinson’s and dementia, and died at a relatively young 71. That keeps me focused on getting on with what matters most, and not worrying much about what anyone thinks of it.
What the two companies actually taught me
Looking back at “smartest and stupidest,” I can be more specific now.
The stupid part was the arithmetic. Two companies do not share overhead in any meaningful way when both are new. Two sets of books, two payrolls, two licensing regimes, two sets of first hires who need a great deal of attention. And critically, twice the number of decisions landing on one person — which is the constraint that actually bites, more than money or hours.
The smart part was the diversification. A new business is fragile in ways you can’t predict. Having two meant one bad quarter in one of them wasn’t existential. That’s a real advantage, and it’s underrated by people who insist on total focus.
What I’d do differently: stagger them. Get the first to the point where it runs without daily intervention, then start the second. The argument for simultaneity is that you’re already in motion. The argument against is that neither gets a proper first year, and a first year is when you learn what the business actually is.
On the thing underneath
I want to be careful here, because there’s a version of this story that turns grief into a productivity technique, and that isn’t what happened.
Losing my father didn’t make me brave. It removed a particular illusion — that there would be a more convenient time. Watching someone decline over years, and then die at 71, makes the phrase “when things settle down” sound like what it is.
That’s not the same as recommending anyone make large decisions while grieving. Plenty of people do and regret it, and I had months where I wasn’t thinking clearly about anything. The estate took nearly the whole year, and I don’t think I appreciated at the time how much capacity that alone consumed.
What I’d say instead is narrower: most people have something they are waiting for permission or timing to do. The timing is not coming. The permission was never anyone else’s to give. It took a death for me to act on something I already knew, and I’d rather other people didn’t need the same prompt.
The practical version
If there’s something you’ve been deferring, the questions worth asking aren’t about courage.
- What are you actually waiting for, and will it arrive? Name the condition. Most of them turn out to be permanent.
- What’s the smallest version you could start now? Not leaving your job. The first real step, this month.
- What would you regret not having tried? Different from what would succeed, and more useful.
- Who would be affected if it went badly, and have you talked to them? This is the one people skip, and it matters more than the rest.
I still miss him. That hasn’t changed and I wouldn’t want it to. But the year that followed was the one where I stopped waiting, and I’m grateful for the nudge even though I’d have preferred to receive it another way.
