Are You Ready To Hang Out Your Shingle?

John T. Mason, Founder, OakHorn Solutions (Former CIO, Hill Country Memorial)

Sometimes life gives you the opportunity to make interesting choices. For example, some of you may have noticed that I haven’t written a Blog post in quite a few months. That was a deliberate decision on my part. Like many choices in life, I had to decide where my energy and focus were going to be, and sitting down each week to write a post just wasn’t going to help, and so it had to take a back seat for a little while.

Let me explain. About 9 months ago, I decided that after 30-plus years working for someone else, it was time for me to strike out, and see if I could make it on my own. A scary proposition to be sure, but exciting as well. If I was going to do this, I really needed to focus to make sure I had everything set up and ready to go. This was the real deal, and I knew I couldn’t just make a rash move. There were people counting on me, and I didn’t want to let them down. And frankly, I didn’t want to let myself down either.

Since that time, I have been asked on several occasions, how I knew it was time, and what had I learned. Here are a few ways to tell if now is the right time:

  • Something on your mind that tells you there is more to offer. Like most people, I have worked in a variety of jobs, organizations and environments over the years. From flipping burgers, leading soldiers, managing projects and leading large organizations, I have seen and done a lot of interesting and difficult things. Each one of these was another experience that I could add to my resume, but more importantly, each was an experience that shaped what I had to offer others. At some point, many of us feel like there are skills and ideas that we can bring to the organization, but can’t share, because of the specific abilities for which we were hired. When you start to feel like there is something that you aren’t providing but could be, it might be a sign that you are ready.
  • You are ‘at a place’ in life that would support a change. Most of us work because we want to provide for our families, or we have expectations that need to be met. But at some point those expectations change, and we find we have more flexibility than we had just a few years earlier. In my case, our last daughter left home this year for college, and suddenly, the nest was empty! No more lacrosse games, no more choir events, and no more dinners as a whole family. Life could support some additional travel, making the decision a little easier.
  • Your family and friends are behind you. One of the things that solidified my decision to make a change was the support I felt from my family, friends, and a fantastic Executive Coach. No one told me I wouldn’t make it on my own. They each felt like I could be successful, supported the idea, and were even willing to risk some short-term inconvenience as I got things up and running. My wife was my biggest cheerleader; if I hadn’t had her support, my decision might have been different.
  • Others will pay for what you do.If your idea or service is worth money, people will pay you for it. And frankly, there is somebody out there who will pay for what you have to offer. You just have to find them. The reason people will pay for your service or idea is because they can’t do what you do.

In my case all the criteria seemed to be met, so it was time to ‘set up shop’ and start my own business. I wanted to provide CIO Advisory services to organizations that might not be able to afford, or find, a CIO otherwise. With my focus in healthcare, my experience in various sized healthcare organizations from very large to rural, and my leadership background, I knew that what I could offer would benefit organizations of all sizes, and allow me to create value in a new way. Thus, OakHorn Solutions was born.

With just a few months under my belt, I’ve learned some valuable lessons:

  • Having funds to cover the startup phase is important. I don’t know about you, but nothing adds stress to my life like feeling I won’t be able to pay my bills. Because of that, having enough money set aside to cover the change in income, especially during the early startup period, will help reduce stress a great deal.
  • You must have at least one client before you take the step. Or, you better be sure that what you are going to offer is a surefire bet. I learned very quickly that the old adage of ‘you are always selling’ is true. But, if you start out without any clients, that job just got a lot harder. I was blessed to have a boss who saw the value of what I had to offer and the value it could bring to the organization, and was able to start out with a client that I knew well! Nothing meant more to me than that sense of support and confidence that she had. Of course, that still left me needing to find some other clients to make ends meet, but starting out with one was a huge help. If you don’t have some clients already lined up, in discussions, or ready to sign as soon as you are on your own, start that process now.
  • Know your boundaries and limitations. It is tempting to think that anyone who is interested in your services is someone you should take on as a client. After all, isn’t that the point? The more business you have, the less you need to worry about finding new business. The problem with this thinking is, regardless of what business you’re starting, there are limitations to your ability to serve the client well. While it seems silly to say no to a client request, remember that you are committing to provide them the level of service they expect. And not only do you need to monitor the number of clients/projects, you need to be sure you don’t agree to do something you don’t know how to do. Just because the client needs something, doesn’t mean you are the right person to do it. Nothing hurts your long-term prospects like not delivering on your promises, or delivering low quality or late services. Your reputation is everything!
  • You need to be able to be ‘alone.’ Unlike typical careers, working for yourself automatically puts you in a position to be working alone quite a bit. You may be on the phone all day, but that’s not the same as being in an office where you can catch up, develop deeper relationships, and spend time face to face. If you aren’t someone who likes to work alone, you may want to consider how your new business will impact that. In my case, I am generally on the phone, or on a video call (Zoom) most days. While it’s not the same, I at least get the opportunity to see who I’m talking with. Otherwise, I would be left staring at my dog while he sleeps all day!
  • Discipline is key. Since branching out on my own, I can’t tell you how many people have asked me how I like working in my pajamas all day, sitting on the couch while watching TV, or getting to sleep in. I can assure you, it’s not like that at all. In fact, discipline becomes even more important. I actually have a very structured day, which includes working out, eating breakfast, getting dressed, and being at my desk by 8 or 8:30 every morning. Certainly it’s not the same as having to ‘clock in’ or be at the office by 7, but frankly, I get up at the same time as before, and frankly I get a lot more done.
  • Getting engaged in community events/groups is critical. I was involved in a variety of community and industry organizations before, but the ability to attend their events often wasn’t possible. In my new business, it’s more important than ever to get engaged in these organizations. Not only is it an opportunity to get your message out and find ways you might be able to help others, it’s also a good way to stay up to date on the industry. It’s key that you attend these events and find ways to connect to the broader community.

Working for yourself definitely isn’t for everyone. With that freedom comes the worry of cash flow, sudden changes to the market, and a greater need for self-discipline and structure. But, if you have the experience and relationships behind you, you are well on your way!

[This piece was originally published on John T. Mason’s blog page. To view the original post, click here. Follow him on Twitter at @jtmasoniv.]


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