You’ve worked overnight for two nights to pay an employee’s mortgage

You might be an entrepreneur if…you’ve worked overtime, over a weekend, or two consecutive days not so that you could pay your own mortgage, but so that you could get money to pay one of your employees’ mortgages.

Anyone who has started a business knows the working life of an entrepreneur differs dramatically from that of the standard 8 to 5 employee. If I required it I’m sure my employees would put in some overtime. I could probably get them to work 60 hours per week for a few weeks, maybe even a month or two. Some of them probably put in some overtime unbeknownst to me. But if I asked them to work until 2am every night, six days a week, for two years, with an all-nighter thrown in once per week, I think I’d start having problems with employee retention. Even if the employees themselves were willing, their spouses wouldn’t be.

If you’re following this series of posts on entrepreneurship, you’ve probably already noticed that I talk about choices a lot, and being stuck between difficult options. Much of what an entrepreneur does is based on what he sees as the potential consequences of his actions. Those difficult choices are provided on an almost daily basis, and they are motivated by three potential outcomes; failure, survival, and success.

Failure only becomes a real option that entrepreneurs consider when they give up hope, and as I’ve stated previously entrepreneurs are filled with boundless optimism. Entrepreneurs don’t believe that businesses fail simply because things didn’t work out, but because someone gave up and made a choice to fail. Or in other words, failure is not something that happens to you, it’s a choice. And so failure is generally not on the mind of entrepreneurs. An entrepreneur will often be optimistic about a company’s future up until the day the company goes out of business.

What is often on an entrepreneur’s mind is survival. In a service-based business like mine, survival depends on three factors; getting work, getting work done, and getting paid, which, unfortunately, often turns out to be a challenge in and of itself.

How do I get work? How do I market our services? How do I spread the word? That’s getting work. Once I get the work, do I have the right people to get it done? How do I keep those people happy and productive? How do I keep them from taking a job somewhere else? If I don’t have the right person, can I find the right person to get the work done? Once the work is done, will the client pay on time? Will the client be able to pay at all? Will the client go bankrupt after we’ve finished our work and leave us hanging for half the project total? Will we have to bug the client for weeks or months in order to get paid? Will the client argue that we didn’t provide what was promised even though we put in two or three times the amount of work we thought we were going to do when we started?

The choices I’m focusing on in this post have to do with the question of getting work done, which means hiring and retaining the right people. One lesson I learned early on was that you can provide all sorts of things to your employees to keep them happy, but if you can’t pay them on time or you can’t pay them on time nothing else matters. Bagels, pizza, books, parties, candy, soda, video games, and the like are great, but they aren’t substitutes for a paycheck. That’s because when an employee has a mortgage to pay, none of those things help him get the mortgage paid. He needs cash.

There have been times when I’ve been unable to make payroll on time. There have been times when I’ve gone six weeks out on payroll. Some employees had savings and were able and willing to stay with the company during those lean times. Some employees had the will but not the ability and had to leave. Some employees had the ability but not the will. Most of my employees, thankfully, have fit into the first two groups. But I know that if I’m late on payroll there will be consequences. If not immediately, then soon. For this reason, I’m willing to do whatever I can to get money in fast so that we can make payroll, and for many years I thought this meant I needed to keep working on something, anything, until we got the money in.

My thought process was that if one of my employee had to pay a mortgage and couldn’t because we didn’t have money for payroll, then I needed to stay at work 24/7 until we could make payroll. And so there have been times when I stayed late for weeks, months, and indeed, years. I can’t count the number of times I’ve stayed late at work, taken a nap from 4am to 6am, and then went back at it working on a website design to get it done faster so that we could finish the project faster and get paid so that we could pay our employees so that they would be able to stay on until the next payroll when the process would often be repeated.

In retrospect, I don’t believe all the late nights were necessary or wise. My wife was very understanding, patient, and supportive during those years, but I can’t deny that it put some strain on our relationship. Today we might be stronger because of it, but knowing what I know now I wouldn’t repeat the experience. What led to a change in my thinking was that I simply reached a breaking point where I said “I can’t do this anymore.” A late night here and there, an all nighter here and there, that I could handle, but I had exhausted my willingness to work late every single night six days a week. While this led to me changing my mind, it wasn’t what changed my mind.

What actually changed in my thinking was when I took a risk and decided to experiment with not working late all the time. I just decided to not work late unless there was a real emergency, and that I would be very selective about what constituted an “emergency.” And you know what? Things worked out. Work still got done just as well if not better than when I was working late all the time. I learned to manage my time during the day more efficiently, I learned to delegate more, and it made all the difference.

I still work late sometimes. I still do all nighters every once in a while. It’s still a rarity that I get home before 7pm. But my schedule seems like a breeze now compared to what it was like a few years ago. I feel like I’m working half-time if I only put in 10 hours. Am I still willing to do whatever it takes to make payroll? Yes. Am I bit wiser about what it takes to get things done? I believe so. Do I always make payroll on time? No, it’s still a challenge sometimes. I am most certainly still learning.