Pippin Williamson

A few minutes ago I finished shoveling all of the snow off of my driveway left there by the snow storm that blew through central Kansas last night. It wasn't a lot of snow, just a few inches, but hand shoveling it all off of a two car driveway with a 10" shovel is hard work. By the end I was breathing hard and relishing the idea of going inside to a hot cup of coffee.

I know that many, especially in my industry, despise the idea of physical labor, but it's something I take great pleasure in. I spent much of my childhood working on construction projects, such as building a three story barn with my father and brother. Physical labor is something I truly enjoy.  It gives me the chance to step away from the screen, work muscles that get largely-ignored, and go back to some of my roots.

This morning, as I was working hard to clear my driveway, I watched as my neighbor cleared her driveway as well, except instead of using a small, 10" shovel as I was, she had a snow blower that made her work substantially easier.

I was working hard; she was working smart.

If I took the time to go purchase a snow blower, or even a leaf blower (since the snow was rather light and fluffy), I could have saved myself a substantial amount of time this morning and every snowy morning to come. It would be the "smart" thing to do. Based on the amount of time it took me to clear the driveway, and considering I will need to do it several more times in the coming months, the cost of a snow blower is minimal when taking into account the value of an hour worth of my time. 

From a business perspective, it would be a better investment for me to work smarter, not harder.

Now, in this particular case, I'm not talking about business, I'm talking about a little bit of manual labor that I thoroughly enjoyed, so working smarter is not so vitally important, but let's apply the same thought process to business for a moment.

Last week I posted my review of 2013, including the overall revenue of my business, Pippin's Pages, LLC. In response to my post, Gary Jones posted a comment to Twitter about how he wanted to work smarter, not harder, and it was something he needed to change.

Working hard is part of the entrepreneurial spirit and life style. Ask anyone that runs their own business successfully and they will probably always attribute a lot of their success to hard work. I know I do. I can look back on the last 5 years and recount numerous times when I worked 30 hours straight to meet a deadline, or pumped thousands of dollars and hours into a project to help move it to the next level.

Working hard is an integral aspect of success. Very, very rarely will someone ever find success without also working hard.

At a certainly point, however, we have to realize when it's time to stop working so hard and instead work smarter. If my business was built around clearing snow from people's driveways, it would be a much smarter use of my time to invest in and use a snow blower than to clear the drives with a 10" shovel. By investing in the smarter method, I could easily double the amount of work completed in a given amount of time, thus possibly doubling my revenue as well.

For the last 4 of 5 years, I have worked hard, really, really hard to build a successful business. Overall I believe it has paid off. This last year, however, I started to seriously analyze how I was running my business and decided to make some changes. I chose to work smarter, not harder.

While everyone's experiences and opinions will differ, here are some of the ways I have begun to work smarter in the last year.

Stopped going at it alone

I have always worked mostly by myself. My business has always been "Pippin's Plugins" and "Pippin's Pages", which is centered around me. There is always a finite limit to what I, as one person, can accomplish.

When I started building Easy Digital Downloads, I made a conscious decision to not do it alone. I actively reached out to other developers and members of the WordPress community in order to build a team around the project. To date, the project has over 80 contributors on Github and more than 8 active members of the development / support teams.

While there will always be projects that I choose to do on my own, such as small plugins or client projects, I have no intention of ever working solely by myself again. Not only is working as part of a team better for the overall production, it's better for my mental health. Over the last year and a half or so, I have learned to truly appreciate the value of having other team members to bounce ideas off of.

I invested in my business

Just as I chose to stop going at it alone, I invested in my business by hiring support technicians to help with customer support, and I began actively paying other developers for "sponsored" development of Easy Digital Downloads.

For an e-commerce plugin, themes are vitally important to the success of the platform. Having themes that customers can be up and running with in a few minutes or hours is huge. I am not a theme developer nor a designer by any stretch of the imagination. In order to get past this, I began sponsoring the design and development of themes for Easy Digital Downloads in order to provide a better, stronger platform for users to build their digital stores on top of.

Paying others to take care of the theme design and development of my business is an investment, but one that I firmly believe will pay off very well.

I could have chosen to work harder by getting better at theme design, or paying others for the designs and then building the themes myself, but instead I chose to work smarter by letting others that are much more qualified take care of it from start to finish, leaving me to focus on what I'm best at, and where I have the most value to contribute: development of the plugin.

I took breaks to walk the dog

Breaks are so incredibly important to the concept of "working smarter". I can recount numerous times in the past few years where I faced real burnout problems from working too hard for too long.

Taking even a 10 minute break to walk around the neighborhood with my dog is a refreshing time away from the screen that helps me focus better when I return to the desk. Spending 30 minutes while "in the zone" will always be more productive than forcing yourself to keep working through two hours of drudgery. If it takes a 20 minute walk to bring back that focus, it's worth every minute and more.

I enjoyed my time not working

Just as taking breaks during the day to refresh my mind and step away from the screen, spending considerable amounts of time not working during the evenings, the weekends, and even in the middle of weekdays is so vitally important. While I often have to convince myself that it is okay to "not work" for two hours in the middle of a Wednesday afternoon, I never regret it when I return to the desk because the next few hours working are much more productive.

I spend time playing with my daughter, taking my family out to dinner, working on improvements to our house, biking, running, playing Xbox with my friends and brother, and other activities that are "not working". Even though they aren't working, these activities are so important to the overall health of my work life. They put my time spent working into perspective and provide an outlook on what I want to achieve with my career.

Focusing on working smarter, not harder, has been hugely responsible for me managing to double my business's revenue over just one year, and over the next year I plan to double it yet again by working even smarter.

I will always work hard--it's in my blood--but one of the integral parts of working hard is coming to grips with how to work harder and more successfully by working smarter.

Pippin Williamson

About Pippin Williamson

Founder and Managing Director of Sandhills Development.


  1. Pippin Williamson

    This is definitely something I can relate to. When I was starting to build my own online business, in the beginning I tend to rely solely on myself. As exciting as it felt initially, too much hard work can burn you out. And unfortunately not all hard work is rewarded – although I do want to emphasize that you have better changes of getting smarter eventually with hard work.

    But the one thing I have realized is that sometimes we are our own enemy. Our sense of what we believe to be important may not necessarily be profitable. And too much attention to detail without a sense of it’s relevance to the big picture can end up becoming a waste of time.

    It was only when I started focusing on what I know how to do best and collaborating with people who are great at what they do have I realized that I can indeed do significantly more than what I would otherwise be able to accomplish.

    I have followed your plugins Pippin since it was still in CodeCanyon. While I have recently focused on automation on CSS via SCSS for Theme Frameworks like Genesis because I’m good at it – I have trusted a lot of my business on leveraging reliable apps and plugins such as yours.

    I would like to be a part of your circle (at least on the CSS, SASS and Genesis Framework side of things). I’m sure we can definitely learn a lot by simply becoming a part of your community. And thank you for the wonderful article.

  2. Pippin Williamson

    Taking breaks. :/ Why is that so hard to do? Why when we’re slumped in chair, brain a numb blur, do we still persist and try to fight on to solve whatever we’re working on?

    And I bet you actually solved many problems while on those walks.

    Did you find having a dog and the responsibility to walk it, helped drag you away from the computer when you wanted to fight on?

    1. Pippin Williamson
  3. Pippin Williamson

    Thank you for this.
    While I have hired two assistants to help me with my business this year, I still am having trouble with taking time off – there’s always more to be done. Maybe thinking about it differently, as part of working smarter, will help me take it this year:)

    1. Pippin Williamson

      I just took my first real time off this holiday season. 2 hours of client work total for 2 weeks.

      Took me 5 years to get to that point and hopefully next year will not be a regression to working through most of the holiday again.

      1. Pippin Williamson


        PS, thanks for your developer constants and email logging plugins – very helpful for my membership site on WPE.

  4. Pippin Williamson

    I hear you! Coming from a background of building custom cabinetry and furniture I learned that the more time I spent planning, the less time I spent actually doing the manual labor. More importantly, the less time I spent correcting mistakes. Mistakes in that kind of business will also cost you money for the materials in addition to your labor.

    You often see professional athletes that are getting older be able to play with the younger, quicker athletes. They usually say they can do it because they learned play “smarter”.

  5. Pippin Williamson

    Definitely buy a snow blower. I never would have, had I not inherited one in 2012, but now that I have one I will never not have one. If it breaks beyond repair, I will absolutely buy one for $400.

    In less time than I could shovel half my driveway (~20min), I can now do my full driveway, all the sidewalk for my corner lot, and the sidewalk for my neighbors down the rest of my block. My experience has improved 100-fold. A++, would recommend again.


  6. Pippin Williamson

    This was the subject of our very first meeting of 2014. We started our web design and development business in 1998 (!) and we’ve worked hard to stay on top of our game. From day one, we’ve never engaged in the race to the bottom (as we’re seeing more and more these days) and as a result we’ve built a good and comfortable life for ourselves. But as you noted, there’s a ceiling to that in your business that is very difficult to break through when you go it alone and when your business is predominantly based on the hours you work (even when you price by the project).

    You have to step back and think about how to work smarter. For people like us, you have to figure out how to “make money while you sleep.” That’s our mantra for this year and the years following.

    I enjoyed your post. Thanks.

  7. Pippin Williamson
  8. Pippin Williamson

    Pippins, I am really impressed how you work smarter. I will also implement these tips in my work life from this year 2014 🙂


  9. Pippin Williamson

    Sound advice. One of the things my college years in computer science have given me is an obsession with optimization, and it definitely helps when you’re trying to make the most out of your time. Gotta watch out though, or excessive planning and no actual work can also happen and cripple your productivity.

    One question, Pippin. How do you go about reaching others. In the WordPress industry?

    1. Pippin Williamson

      Making myself open and actively reaching out to others, whether it be for help, advice, feedback, etc, is a great way to reach others. Oh, and just being friendly.

  10. Pippin Williamson

    Me too, after spending countless hours in front of the computer in the last years I decided to cut it down. And it works! Amazingly I actually achieve more with less effort. 😉
    Taking breaks helps me keeping the focus on what’s really important.

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