I realize that the majority of what I write here has to do with WordPress development and topics that are tangential to that (like my opinions on certain issues around the software). But one thing that I rarely talk about is how things are going with respect to running a business that’s built on top of said software.

Right now, in technology, it’s hip to be a part of a startup, to aim to be something that’s emulating what’s happening in Silicon Valley, or that’s trying to create the next big thing by bootstrapping your business or by accepting some type of capital.

And all of that is completely fine. For whatever it’s worth, I think it’s really neat reading how others approach building a business and developing their product or service whatever it may be. My story simply isn’t like that – it’s not the kind you’re going to see on Product Hunt, Hacker News, or any of those other types of sites.

All of that’s okay with me. It’s not – nor has it ever been – what I’ve aimed to do with Pressware.

In short, Pressware would be classified as a bootstrapped company (that’s undergone a few name changes since the LLC was formed – a story for another time) and out of which I work in order to help provide solutions for other people using WordPress.


That’s it all there is to it.

Anyway, I thought it might be interesting – if anything – to begin sharing my experience as to what it’s like running a business based around WordPress and how I deal with some of the challenges that it presents outside of development.

I don’t know if any of this will be helpful to those who are working within a larger company, running their own business, or serving as a contractor in any other type of industry, but who knows?

Some of the posts that I’ve written in the past that I thought were boring and almost never published ended up becoming those that resulted in interest and genuine discussion. (This is also why I think other people need to speak up and contribute to the blogosphere. :)

With said that, one of the things that I’ve had to learn how to handle as the years have passed is handling red flags as they come up.

What Are Red Flags in Business?

The terminology of a “red flag” is probably something that’s used differently depending on where you work (or how you use it in your own life). So, for me, here’s how it works:

I calendar everything. And if it’s not calendared (is that a word?), then it’s set as a reminder. So if I don’t have something telling me where I need to be and when, then I have something telling me what I need to do and when.

It’s how I work. My MO, even.

Though this is how I work best, it’s not always the best approach (though it’s optimal given my personality type). The reason being: If something comes up at some point in the day that hasn’t been scheduled, reminded, or emailed to me, then I have a hard time figuring out how to add it to my schedule.

That last sentence makes me sound like a doofus (and maybe I am), but bear with me.

Sure, I guess I could bump something, but usually I have things set out days or weeks in advance in order to avoid this problem.

Anyway, for me:

A red flag is anything that comes up during the course of the work day that I didn’t prepare for and that derails my current course of work.

And for anyone who does any type of work (read: pretty much all of us), this is not uncommon. It’s unavoidable.

But that’s it. That’s what I consider a red flag. Some people consider them fires to be put out, and some people probably use some other term that I’ve not heard. There you go, though.

Dealing with Red Flags

One of the conveniences that I have in working from home is that if I’m able to work through enough items in my schedule and my reminders then I normally try to take at least one hour a day to exercise.

Overly Manly Workout

As of late, this time has been coming later and later in the day so I try to actually do it whenever the kiddos are asleep – that way, I’m not cutting into time that I could actually be spending with them, and I’m still getting my work done. Furthermore, I have the opportunity to come back to work for a couple of hours when I’m done.

It’s a nice break in the afternoon.

But what happens when you normally have a set schedule to which you try to stick, you come back to your inbox after your exercise, and your inbox now includes several high-priority actions that must be handled prior to to getting back to the things that you needed to finish in the first place?

I know – this isn’t unique to me, and I’m not trying to pretend it is. I’m just walking through how I deal with it.

Ultimately, this means that I’m going to need extra time at the end of the day to get everything done that needs to be done which means that I’m now cutting into time that I would usually be spending with my family doing whatever families do on a given afternoon.

So in all of my glorious attempts not to cut into time that I’m spending with them, I’m not cutting into time that I could be spending with them.

On the flip side, this is the very thing that helps to put the proverbial food on the table that we’ll be proverbially eating later that proverbial night so it’s not like I’m spending time trying to finish off something that doesn’t matter.

Proverbially speaking, of course.

"This is where the fun begins."

“This is where the fun begins.”

See the two sides of this? There is where it’s gets fun.

Taking Down The Flags, Putting Out The Fires

For me, I usually end up doing one of two things:

  1. I go ahead and handle the issues as they come in and work a little bit later, or
  2. I end up taking care of the highest priority issues, stopping work at five, and then coming back to work after the kiddos are in bed

And this is generally how I’ve worked for the past few years, but there’s one part of this that is understated and that’s support that comes from my wife. For you, it may be your husband, your partner, your boyfriend, your girlfriend, etc., etc.

No matter how you look at it, handling things like this when you’re responsible for providing for the family and for making sure that those who have contracted you have the solutions that they need can be a tough job, but it’s not a one person job.

I wouldn’t be able to be self-employed, married, and helping to raise two kiddos (and two crazy dogs) were it not the support of my wife.

So when it comes to managing red flags in business, yes there’s a significant amount of work that goes into handling unplanned issues as they arise, but it’s also not without talking through it with Meghan first.

Sometimes, extending my working hours a bit is what works best. Sometimes, working after hours works best (she has her own photography work to do after hours as well, so sometimes that works out well for both of us).

But whatever the case, I’ve found that regardless of which option that I take above (that is, extending my work day or working later), it’s far easier to figure out the course of action to take after talking it through with her and what’s best for the family on any given day.

We’re All Different

With all of that said, what works for me probably won’t work for you. Or maybe it will. I don’t know. But I’m speaking through the experience that I’ve had and what we’ve found works best for us and ours.

This hasn’t been an overnight revelation.

Self-employment is a lot fun, but it – like anything – introduces it’s fair share of challenges, as well. To that end, know that if you haven’t faced anything like this (or you’re currently working through it), then this is something that we all have to figure out.

It doesn’t have to be some huge battle either. It’s far easier to look a the schedule that you have for yourself and your family and basically triage your issues. If you have to extend the work day, cool. If you have to work late at night, that’s cool, too – as long as whatever option that you choose is something that has buy in from whatever parties are going to be affected the most.

For me, that happens to be my family. I wouldn’t be able to do what I do were it not for their support, so I try to reciprocate the support as much as possible by making sure that I’m not taking advantage of it.

With that said, I’m curious how the rest of you – regardless of if you’re self-employed or not – handle this kind of stuff. After all, maybe I’m missing something. I figure there’s always an opportunity to learn.

So how do you handle trying to take care of red flags as they arise whenever they don’t go according to your schedule?