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.

Pressware

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?

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Join the conversation! 9 Comments

  1. I might have a different definition for my red flags, but to me it’s when a client decides to throw me a curve ball by asking (then demanding) something be done that’s outside the scope of the project . Oh…for no additional cost.

    This happens all too often. So much so that I’ve started nailing everyone down with detailed contracts. As first, I was too chicken to say no: “Oh, now you want this kind of functionality that will take me 10 more hours to implement that was never discussed? Ok….I guess so.”

    But I had to put a stop to that nonsense. Now it’s a polite “I’m sorry but that’s outside of the scope of our current contract but I can work up the additional cost.”

    • I think your definition of red flag is fine – they are kind of relevant to the context in which you’re working and the example you’ve provided is really good.

      You’ve offered one of those pieces of advice that is one of those things that anyone starting out on their own should learn from others who have been there before them. It would save a lot of pain, loss of time, money, and possibly sleep (not to mention frustration).

      Either way, you’re on point.

      • Well Tom let me be honest and tell any noobies reading that this hard line stance on charging for anything outside of the scope costs me the occasional client. It goes a bit like this:

        Client: “Oh, by the way, we must also have “this” functionality on our site.”

        Me: “That’s not a problem. It’s outside the scope of our agreement but I will work up the additional cost.”

        Client: “Actually what we’re asking for doesn’t seem to be a big deal and we’re not prepared to pay anything more. Can you just handle it?”

        Me: Actually what you want will take “X” more hours to complete so I would in fact have to bill you for the extra time.”

        Client; “If that’s the case just stop work on our site and we’ll search around for someone else. Thank you.”

        Doesn’t happen often….but be prepared.

  2. Tom, as you know I follow your musings with great interest; you’ve always struck me as about the smartest WordPress guy around, because you seem to “get it” with “it” being something that far exceeds being a PHP/CSS jockey.

    You’ve outdone yourself here.

    How? By being open in a way that very few people are comfortable being. Here’s where I’m coming from.

    As you may have surmised by now, the grand experiment that is The WordPress Helpers is very likely to end … or at least morph significantly … soon. This makes me sad because as its architect I know what we were after and it had nothing to do with being WordPress geeks or a resource (solely) for people who are. Built out, TWPH was going to be a resource for WP geeks, users, and business operators to come together and make their burdens easier to handle.

    That message got lost along the way, and that’s the comment I’m making here and that your story made me think about this morning.

    I’m a business and publishing guy from way back (see http://answerguy.com/about-the-answerguy-2012/yablon/ , if you’re interested). I “came to WordPress” about six years ago, and I have some technical ability, but I always saw it as just a tool, albeit one that’s pretty terrific in a lot of ways. But that said, my company does a lot of marketing and technology (marketing technology?) consulting, a great deal of it has to do with WP, and when the light bulb went off for me last year and I decided to try and build a thing that was useful across disciplines, TWPH is what came out.

    Forget the trademark arguments; they’re insignificant compared to what “the community” thought (refresher: http://wordpress.answerguy.com/geek-fight-and-community/2015/01/01).

    All of this is about shifting business and life environments, perception, and your adaptability to them.

    Your story reminds me of … well, me, about twenty years ago. I too ran a consulting business from my home, with what your story suggests to me were very similar motivations to yours. And it was successful. And I never felt as though I was “done”, or “there”.

    THAT, my friend, is what makes for a smart, compassionate businessperson. And you are clearly that. Keep questioning the decisions you’ve made; it’s what will drive the even greater ones you make moving forward.

    • Tom, as you know I follow your musings with great interest; you’ve always struck me as about the smartest WordPress guy around, because you seem to “get it” with “it” being something that far exceeds being a PHP/CSS jockey.

      I appreciate the compliment, Jeff – but there are far, far smarter people involved in WordPress. I’d love to be there one day but, in the meantime, I’m doing what I can to get there :).

      How? By being open in a way that very few people are comfortable being. Here’s where I’m coming from.

      I think this is definitely true for some; however, I think the open source community is also very used to being, ahem, open about certain things.

      For example, some are super open about their financials over the course of the year. I respect that, but I’ve never been able to personally make that jump yet. Maybe one day. Who knows. I think I’m just open about the things that I hope help other people, but that will also help yield some type of useful conversion such that I can also learn from other people.

      Keep questioning the decisions you’ve made; it’s what will drive the even greater ones you make moving forward.

      Definitely aiming to do that – only a daily basis even. Sometimes I think I’m headed in the right direction, other times I feel the need to step back and evaluate where I am.

      So far, so good. We’ll see what happens, though :).

  3. Hey Tom, I’ve always appreciated your insight on things because you have real experiences to speak from. I can relate to your experiences a lot, and being married 11 years myself I know the importance of a wife’s support.

    Thanks for your openness. If I can be honest for one moment to say, you don’t need to always explain yourself so much about your topic choices. I know so many faithfully read your input because they value and put stock in your opinion, but I feel like every risk you take you preface with an explanation and you don’t always need to. Perhaps it’s just part of you, like for me my wife says it’s annoying that for every point I make I give an example/illustration. Although I feel I’m being clear and helpful, she says it can come across condescending/patronizing. So because I love your input I trust the reasoning behind the inspiration of your topics and I just want to get to them. Love you man, hope that wasn’t harsh.

    • Hey Tom, I’ve always appreciated your insight on things because you have real experiences to speak from. I can relate to your experiences a lot, and being married 11 years myself I know the importance of a wife’s support.

      Thanks so much – nice to hear from someone who’s in a similar situation. Always dig from others who can identify from where I’m coming.

      Thanks for your openness. If I can be honest for one moment to say, you don’t need to always explain yourself so much about your topic choices.

      Absolutely appreciate this feedback, Nick.

      I know so many faithfully read your input because they value and put stock in your opinion, but I feel like every risk you take you preface with an explanation and you don’t always need to. Perhaps it’s just part of you, like for me my wife says it’s annoying that for every point I make I give an example/illustration.

      Yeah – I’ve definitely been told this before. At this risk of sounding like I’m totally you ignoring your statement, it’s not without warrant:

      In this field, I’ve made the mistake of not providing enough disclaimers such that people have read what I’ve said and than commented that I’m speaking as if I’m writing the law of the land, so to speak. That’s not the case, of course! I’m just trying to offer experiences from where I’m coming from.

      I’m always open minded to hear where others come from, too! But when I fail to provide enough disclaiming, I’m afraid the comments will be derailed into something that’s off topic from what I intended.

      I guess I’m a little gun-shy. That’s something I should work on, for sure :).

      Although I feel I’m being clear and helpful, she says it can come across condescending/patronizing.

      It’s a tough line to walk, isn’t it? I mean, that’s the last thing we want to do. But alas.

      So because I love your input I trust the reasoning behind the inspiration of your topics and I just want to get to them. Love you man, hope that wasn’t harsh.

      This wasn’t harsh at all – I seriously appreciate this and am glad you felt comfortable sharing! I’ll definitely take it into account the more I write. If you see similar posts with fewer disclaimers and all of that, then you’ll know you helped play a part in that :).

  4. Hi Tom:

    This post strikes a chord with me. I find it easiest to work in long stretches on a single project per day. There are days though when I get bombarded with client requests that are time sensitive.

    Since there are only so many hours in a day, this is a dilemma.

    I do my best to plan out my day, and only do two or three items in one day. Whenever possible, I plan my week around longer projects.

    Like a lot of people in the web development community, I can find myself spending more hours in from my computer than is healthy.

    Our kids are older, so that reduces part of the burden. I do take regular breaks at morning coffee, dinner and before bed to spend time with my partner in crime, Amy. I keep it in mind that spousal relationships are of prime importance. Deadlines may loom at times, but family time is essential.

    I need to start time-boxing much better than I have been recently. I do schedule calls, but I having a small time buffer each day helps also.

    Good to hear folks talk about more than code. That’s just one vehicle for making things happen in the world. The intent is what matters, and there’s more to life than development. Also, good interview you did with Jeff from WP Tavern a week or two ago.

    • This post strikes a chord with me. I find it easiest to work in long stretches on a single project per day. There are days though when I get bombarded with client requests that are time sensitive.

      Since there are only so many hours in a day, this is a dilemma.

      Yep – I’m really strict about the time that I spend on the number of tasks that I’m working on and if something comes in that’s not part of what I’m focused on right now, then I normally just snooze it until later (where later may even be tomorrow).

      Like a lot of people in the web development community, I can find myself spending more hours in from my computer than is healthy.

      For sure. The thing that changed this for me the most was having kid. Granted, that’s not a choice or an option that some people make in life and that’s fine – I’m not saying it’s better to have or not have – I’m just saying that that was the personal kick in the pants that changed it all for me.

      Now, sometimes, I wish I had a little less to do during the day (though if that were the case, work would be slowing down and I don’t want that to happen).

      Our kids are older, so that reduces part of the burden. I do take regular breaks at morning coffee, dinner and before bed to spend time with my partner in crime, Amy. I keep it in mind that spousal relationships are of prime importance. Deadlines may loom at times, but family time is essential.

      Couldn’t agree more. When 5pm hits, I’m usually away from my desk and my phone and all in with my wife and kiddos.

      Good to hear folks talk about more than code. That’s just one vehicle for making things happen in the world. The intent is what matters, and there’s more to life than development. Also, good interview you did with Jeff from WP Tavern a week or two ago.

      Thanks for saying that – glad to hear the feedback on that :).

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