In a blog post last summer, I wrote about how to know when to go all in as an entrepreneur. One of those criteria is “Family“. I listed that one first, because ultimately, you can make more money, you can get another job, you can start another business, but if you alienate your family – mainly your spouse, but certainly your kids – that’s a lifetime loss. Before you can “take the dive”, “make the jump”, etc., your family has to give you that freedom to fail or to succeed.

From that blog post:

If your spouse is not on board, don’t do it. I cannot emphasize this point enough. Do not let your business be the elephant in the room that you don’t share with your spouse. Do you have kids or kid(s) on the way? There are a handful of events that can cause extraordinary stress in life and in marriage. Babies, homes, jobs, businesses, weddings are all among those. It’s generally not a good idea to do more than 1 or 2 of any of these things in a given year.

My Lack of Freedom

I had started the business entity that would eventually become CWNP (after 4 failed ideas and 2 name changes) a couple of years before I went all in full time. During that time, I was employed by FirstData. Part of that employment was relocating to Denver, Colorado. We were thrilled to get to live in the wild west, and my wife absolutely loved it. That was the easy part, since FirstData moved us out there, paying literally every moving expense in the process.

But I hated my job. Within a couple of months at FirstData in Denver, I realized I was miserable being one employee among 40,000. What gives me energy is having the ability to move the needle in any organization. I don’t have to be in charge, but I have to have autonomy and my work has to actually matter. In a company of 40,000 employees, I got no indication of either. But I couldn’t leave, because if I left within a year of the relocation date, I’d have to pay back every penny of the relo costs.

We Need to Talk

So, I waited. And waited. And worked nights and weekends on the thing that would become CWNP. Then, 50 weeks and 1 day after my relocation date, I gave my two weeks notice. However, before I could do that, I had a really deep, painful, long, heartfelt, passionate discussion with my wife. Here’s how that conversation started:

Darlin’, as you know, I really don’t like my job. What I’d really like to do is quit that job and put everything into my business, work from home for a while, really live lean. That’ll mean a pay cut, benefits will go away, and I might not make much money for a while, and it might fail altogether.

I tried to be as honest as I could, put it all out there, and really make sure we got to the meat of the matter. I had a really cushy position at FDC, and the benefits were by far the best we’ve ever had, and they had moved us to Colorado! But I could not take it any longer, and I really longed to run my own show. Here’s how that conversation ended.

“Go for it.”

I lay my heart and soul out on the table, and that’s her answer? Yep. I knew from that moment on that I had the freedom to succeed, or fail, as an entrepreneur. Since that day, I have had many similar conversations with my wife – and now my kids – to lay out what is about to happen next. It is so freeing now to have succeeded and to have failed (multiple times), and yet still be here, living the life.

People in the startup world talk a lot about failure as a badge of honor. It’s not. It sucks, but it builds a lot of character, and you’re better for it. If you don’t have the freedom to fail, then you can’t possibly have the freedom to succeed.

A shorter version of this story is on the dedication page of “Practice Your Pitch”. I wouldn’t be here doing this today if my wife’s response had been different.

What do you think about that?