An Entrepreneur’s Valentine’s Day Challenge

Today is a good day to object to all the phony entrepreneurship lore that has people putting aside life and love for business. The whole mystique of giving it all, being obsessed, and burning the midnight oil, while it might inspire some, leaves me as cold as ice. It’s a ruse. Don’t buy it.

Despite the common myth to the contrary, business passion, persistence, and perseverance do not guarantee business success. Using your business as an excuse to ignore relationships, people, and family is a mistake. Do what you love, yes, and love what you do; but stop it, often, to love life and the people you live it with.

I don’t like Valentine’s Day. Words of love issued on Feb. 14 seem a bit like the last-minute chocolates, flowers, and sweet-smelling upscale soap in the picture here: contrived, diluted, over-wrapped, and useful only at the last minute, if at all.

So today on Valentine’s Day I refer to something I wrote in the normal course of business, on a day that wasn’t Valentine’s Day. In Relationship vs. New Business, originally written in March of 2009, a student had asked me in email:

Would you have still left your job and ventured out on your own if your wife were absolutely unsupportive and opposed to the idea?

I said no. And answering the question reminded me of how important my wife’s support was to my own career. This is from my answer:

This is a tough question, obviously. Every case is different.

But we do glorify the entrepreneurial a bit too much, and we glaze over some of the risks involved. Sometimes. I know, my answer sort of spoils the story and the rah-rah of entrepreneurship, the idea that we follow our passion and overcome all obstacles. But it’s the truth. Businesses fail, and it’s naive of us to forget that sometimes they fail despite our best efforts. Sometimes the reluctant spouse is just plain right. Sometimes the failure to get investment, the obstacles that accumulate, are a message.

And looking at it realistically, there’s no denying, like it or not, that a spouse who doesn’t buy into the dream adds to the risk. You don’t want to throw the family into the mix. Plan more, research more, and either answer the objections or accept that the world is sending you a clue. Keep your job. Gulp: if you still have one.

Here’s a true story: Before I left a good job to strike out on my own, my wife said “go for it; you can do it.” And she meant it. At several key points along the way, she made it clear that we would take the risk together. There was never the threat of “I told you so; why did you leave a good job, you idiot!” What she said was “if you fail, we’ll fail together, and then we’ll figure it out. We’ll be OK.”

That was in 1983. Failures, dark times, three mortgages and $65,000 in credit card debt at one point didn’t help our relationship. But what we started back then survived, and so did we; we’re still married.

There are two entrepreneurs in that true story of the conversation with my wife, not just one. And entrepreneurship and relationships, if you want both, take two people.

Today, on Valentine’s Day, there’s still room for a reminder that real relationships are important for the other 364 days of the year, too. Say it right today, yes. But live it, don’t just say it.


  • Jake P says:

    A fantastic reminder, Tim. I premeditated my departure from corporate life about 9 months prior to making the actual move, saving money and cutting expenses. My wife was 100% on board the whole way — even though she was a stay-at-home mom and we had two kids under five, and I was quitting a 6-figure salary. Her confidence in me was instrumental to my success.

    Today, we laugh about how shocked she was when I walked in the door with “my box” after finally telling my boss I’d had enough. Since we’d saved up a bunch of money, the first thing we did was go on a (very frugal) family road trip in a borrowed RV for a couple of weeks. The memories from that journey, and the re-connection to my family, enabled me to make a fresh start. And working for myself has enabled me to *stay* connected in ways that simply weren’t possible working 7-7 for someone else.

    • Tim Berry says:

      Thanks Jake. There’s another good reminder. And if you go to the comments on that earlier post, there are more of them there. All very welcome. Tim

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  • Darren Bond says:

    Indeed. Either way, the outcome is the same.

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