Changes

Over seven years ago I started fixing people’s websites in my basement for extra cash, and I quickly found out that I really liked doing it.

I found out pretty quickly that solving difficult problems for people was something that brought me real happiness, and it wasn’t long before I left a cushy full time job to head out on my own so I could do what I loved full time, and on my own terms.

The demand for our work grew quickly, and we slowly added more and more people to our team. At one point in 2016 we had 11 full time employees; an entire soccer team of web pros!

Getting Lost In the Business

As the team grew, I slowly moved further and further away from the reason I started my business in the first place. It’s a trend that’s talked about extensively in the E-Myth. People start a business because they love what they do, but then the growth of the business, management of people, and demands of administrivia become too much, and the person who started the business finds themselves in a totally foreign land with no roadmap for how to get back to the thing they once loved.

I remember reading that book at some point early on in my entrepreneurial career and thinking “I’ve gotta make sure that never happens to me. That can never ever happen to me!

Well, it did happen to me…

Over the last few years I’ve found myself in situations I never could have imagined. There have been incredibly high highs, and some of my very lowest lows.

On multiple occasions we’ve watched as companies we’ve worked with have reached massive success. Whether their definition of that was doing a million dollars of revenue in 30 days or selling 100 copies of their first eBook, our team has helped facilitate some pretty remarkable things over the years.

On the flip side, some of my darkest life memories stemmed from situations or circumstances directly related to my company.

Charles Dickens Was Pretty Smart

Remember in A Christmas Carol when Scrooge watches his own life from the outside while he sees his past, present, and future self make horrible decisions?

While I don’t think I really ever carried the demeanor of Ebenezer, I feel him. Today I look back and often think “what might have been…”; or I try and replay a decision or direction that might have turned out better had I known then what I know now.

But hindsight is 20/20, and this isn’t a pity party. At this point all I can do is learn from the experiences of the last years of my life and make sure I tip that nice boy from the neighborhood an extra schilling for hauling my prize Christmas turkey.

If you’re a leader in any capacity, and you feel like you’re drowning, you need to know that none of this is easy, and you’re definitely not alone.

How Do We Keep Our Business From Owning Us?

If I could condense everything I’ve learned into one simple piece of advice, I’d tell people to ask for help before they think they need it.

That can happen in all sorts of ways, both in business, and personally too. For me, not having a firm grasp on lots of operations-related business tasks resulted in me spending way too much time trying to figure them out on the fly. I hated doing them and I wasn’t any good at them, which is the perfect recipe for a dog 💩sandwich.

But going way beyond business, there were many times I felt smothered and didn’t know where to turn, or if I’m being totally honest, I was too prideful to seek outside help.

I’m a smart guy,” I’d tell myself. “I can figure this out.”

I learned that the line between confidence and stubborn stupidity is infinitely fine, and that I was often on the wrong side of it.

Now I see a therapist regularly. We talk through the hard things. The places I feel inadequate and what I’d like to see improve. I don’t always leave with all the answers, but I do create the space for myself to talk about the things I’m worried about or want to change in my life.

It’s a process, but so is everything that’s important, right?

The Future

I’m burying the lede in some ways here. I sold my company this month, but that’s not where I wanted to point the spotlight, even though it is something I’m really excited about.

I’ll be working for Southern Web, the company that bought WP Site Care, and I’ll be back to doing what inspired me to leave that cushy desk job six years ago. I’m going back to helping people solve problems in their online businesses.

It’s a remote position, so we aren’t uprooting to Atlanta or anything like that. We’re staying right here in Utah. After this initial transition period I’ll be able to focus on the work I enjoy, spend more time on my personal health (it’s been totally neglected), and be more fully present for my wife and boys.

Finally, if you’re feeling helpless, or alone, or like your business runs you and not the other way around, raise your hand and ask for help before it’s too late. Don’t wait for as long as I did. There’s a whole world of professionals and a great community of people who are ready and willing to help. If you’d like to talk through your struggles or just need a place to vent, I’m happy to have a conversation anytime. Shoot me a note or DM me on Twitter.

The very last thing I want to do is thank those of you who have stuck by me and lifted me up when times were incredibly tough. I’m so truly grateful for your help, and you’ll never really know what a difference you made in my life during a time when I otherwise felt completely alone.

Thank you thank you thank you.

22 Comments


  1. Hey buddy,
    I have said on a couple occasions that I look up to and this is why. I appreciate your honesty. I feel lost at times, too, and I don’t have a biz the size of WP Site Care. I think a good many folks feel what you feel. And I’ve been seeking help, too, and started speaking to a therapist also. I have been applauding you since the very first shitty PowerPoint presentation of yours I saw in Vegas years ago.

    Proud of you.

    Reply
    1. Ryan

      Wait you thought that PowerPoint was shitty?! 😂😂😭😭

      (It for sure was)

      Reply
  2. Megan Gray

    I thought it was a fine PowerPoint. (and you are a very great person.)

    Reply
    1. Ryan

      Thank you (on both accounts). Right back atcha. (Please don’t picture finger guns. No finger guns were intended)

      Reply
  3. Toni Sullivan

    You have a gift for writing & sharing your insights & feelings in a way that we can all relate to & learn from.

    Through your process, you have much to be proud of in spite of the challenges. Celebrate your successes as you move forward, & make this new direction the best choice for you, your family, & your new company. You’ve got this, & you’ve got a lot to offer!😍
    Love you!
    Toni

    Reply
  4. David Lloyd

    I don’t have a website you can fix, but I like reading your stuff. I also like spending time with you and I like food (in ascending order). Wink 😉

    Reply
    1. Ryan

      Are you asking me out? (The answer is yes)

      Reply
  5. Terry

    Oh my sweet Ryan. I’m sitting here crying. For what you have gone through and you strength to confront it get help and go forward. I applaud you and want you to know how much I admire you and love you to pieces💜💜💜💜💜

    Reply
    1. Ryan

      Thank you Aunt Terry. Love you ❤️

      Reply

  6. Ryan, congrats on the change! I feel ya too in the entrepreneurship sense. I love that book too, and I’ve found myself get lost a few times along the way.

    Also, therapists are fantastic. I keep thinking “Ah, I don’t need to do this anymore…” and a few months later I’m back there in his office getting it all out. It’s part of my self-care/maintenance practice now. Like going to the chiropractor (also a fantastic thing for us desk jockeys) and working out at the gym or going hike.

    I’ve always looked up to you for the helpful, generous person you are, and I wish you the best in your continued success!

    Reply
    1. Ryan

      Thanks Dustin. Keep up the good work!

      Reply
  7. Alex McClafferty

    Congratulations on starting the next chapter, Ryan.

    The message you’ve shared about mental health is a powerful one and cannot be understated. Your point about being a ‘smart guy’ is great as well; I was just writing about how everytime I’ve opted for hubris over humility, I’ve found myself in BIG trouble.

    All the best, Alex.

    Reply
    1. Ryan

      Love the way you phrase that! Hubris over humility… good stuff 🙂

      Reply
  8. Michael Telford

    Congratulations on the exit! I am happy you are back doing what you love. If you ever want a hiking partner hit me up. 😀👍🏻

    Reply

  9. I don’t know you, but I know the feeling.

    I love how you’ve handled it, hope you feel full of zest now or soon.

    Reply
    1. Ryan

      Appreciate that, Lewis. Thanks for stopping by! Cheers.

      Reply

  10. I so hear you on this and I only run a one-person company. Glad to hear you’re getting back to what you love!

    Reply
    1. Ryan

      Thanks Jennette! I’m happy about it 🙂

      Reply

  11. Hi, I googled to find out more information regarding the switch from wpsitecare to southern web. Wanted to tell you that every time I spoke to you regarding my website I’ve always thought that you really care about my small business and you want to help it succeed. So keep doing what you are doing. Looking forward to continuing growing under your care.

    Reply
    1. Ryan

      Really appreciate the kind words and validation, Leah! It’s always been very important to me to be an advocate for small business, so I’m glad we can get back to doing that!

      Reply

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