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Is it strange that I spend a lot of time thinking about legacy? At 28, it might be far from the forefront of the minds of most of my peers. But, I find myself often asking  “have I done my family and friends justice?” “If things come to an end, did I make a difference?” “Have I left my mark?”

As the steel cylinder I am in rattles and rolls, dips and is tugged by the strings of gravity and man’s invention, I find myself considering continuity. Personal and business. I ask myself questions like; Who would take over these companies I’ve slaved over? Is there enough money in the operating account to buy whomever the time to get up to speed? And what of my personal finances? Are my obligations going to be met, and those around me taken care of?

Morbid Practical

If you find yourself having similar thoughts, I’d like to offer you some of my own.

I’ve worked my tail off to get my personal and business balance sheets in order. Especially these last couple years where these thoughts have come to the forefront. I stopped being a total jackass, and despite my spendthrift tendencies, I got my sh*t together. I figure you want to be able to have money in the bank to run the business and meet your personal commitments for 3-6 months.

A Will

I haven’t dealt with this yet, but it’s high on my list of priorities.  When I spoke to my family lawyer about this, she told me that most folks leave this way too late, or never do it at all. A big mistake in her (somewhat biased I am sure) opinion. The way I see it, if you care about the people you love, you won’t cause them any more stress than your passing will already create. And it’s not that time consuming/costly to do this.



Get yourself sorted with some life insurance. Even something basic.

I spent 15+ months putting my policy together. I went through 2 guys before I eventually found someone I could trust. Listen very carefully. The person you pick may have to go to bat for you one day. Head to head with HUGE corporate lawyers who don’t want to pay you and your family dick all  Choose someone who will fight tooth and nail, and has a proven track record of doing so.

An extension of the last point, but deserving of its own; work with someone who will take the time to explain things to you. These policies are confusing even to people who’ve worked in the biz their entire lives. Take as much time to understand every bit of your policy. If your provider is rushing you, and not walking you through everything, ditch ’em.

My rule of thumb is buy enough to cover what you owe. In my case, that is a couple of mortgages. I want these to be paid in full if something went down.

Consider other forms of personal insurance like disability and critical illness. Car accidents and cancer are no joke, yo.

You aren’t invincible. I am, you aren’t.


Now, what of the business? I thought you’d never ask.

If client’s stop paying, do you have enough money in the operation account to survive for 3+ months?

Who steps into the CEO’s shoes? I’ve been thinking of swapping jobs/responsibilities with a team member or two so that they might be able to gain significant insight into my day to day. Having someone ready, even if just for a transitional period, would be a wise play.

Someone smart once said, you don’t have a business if you need to be around to run it. And so, have I put together sufficient processes, guides, controls, etc. so that things will keep moving along to a similar standard and tune?

I’ve dedicated the best years (so far) of my life to the businesses I’ve built, and the people that run them. I don’t want to leave people with a sour taste in their mouth. I’ve sacrificed too much and worked too damn hard!

What do you think? Do you find yourself thinking about these things? How have you navigated them?


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