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 on purpose, and 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 me with a few things that were on my plate at the moment. While sharing knowledge about leadership, technology and influence are important to me, it had to take a back seat for just a little while.
Let me explain. About 9 months ago, I made a decision that it was time for me to make a change in my career. After 30+ years of working for someone else, I had decided that 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 over the coming months 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.
So in those months, I prepared, prayed, talked, read, planned, read some more, and got my plans laid out and accomplished so I was ready. I certainly couldn’t have been accused to making a quick, or rash decision. In fact, I was probably ready for the move long before I thought I was.
Since that time, I have been asked on several occasions, how I knew it was time, and what had I learned. Great questions, and for the first few months, I didn’t think I was qualified to answer them. However, now that I have a few months under my belt, I thought it might be a good idea to share my new-found experiences just in case you, or someone you know is thinking it’s time to strike out on your own.
When is the ‘Right’ Time?
First, I think it’s important to remember that every situation is different. What works for me, my timing and skills and my readiness for change likely won’t be the same for anyone else. We all come to our work and lives with different experiences, skills, personalities and personal life expectations that make the timing different. For example, I know some people who, despite the external environment being ripe for a chance to strike out, would never do it because their internal fears and needs would never let them. Not for million years!
If that’s not you, and you have been giving it some thought, there are a few ways to tell if ‘now’ is the right time. If not now, once some of these things are in place, the time might be right.
- You have 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 one 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, mostly because they need the specific skills or abilities that they hired us for. Not that most organizations won’t take ALL you have, they just don’t need some of the skills as much. But, when you start to feel like there is something that you aren’t providing, and 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, we need to support our habits, or we have expectations that need to be met. But, at some point those expectations change, and we find we have more flexibility that we might have 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, not a single person, told me I was crazy and wouldn’t make it on my own. Without exception, each one 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, and without a doubt, if I hadn’t had that support, my decision might have been different.
- Others will pay for what you do – I know, you have a job and someone pays you to do that. But if your idea, your service or your ‘thing’ are 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/idea is because they can’t do what you do. So, if you find yourself there, and you know someone would be willing to pay for it, that’s a great start.
All these criteria seemed to be met, so it was time to ‘set up shop’ and start my own business. I wanted to provide Chief Information Officer (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.
But, with just a few months under my belt, I’ve learned some valuable lessons that might help you as well. Here is just a bit of what I found to be true.
- Having a source of funds to cover the startup phase is important – I don’t about you, but nothing adds stress to my life like feeling I won’t have the money I need 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. I don’t know what ‘enough’ is, but nothing is definitely not enough! In my case, I’m glad I had a startup fund. The last thing I wanted to do was to go into debt, or remortgage the house so I could still pay the bills.
- You need to have at least one client before you take the step – Or, you had better be sure that what you are going to offer is a surefire bet. I have 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 also 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 starting out – 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 thank you to a client request, remember that you are committing to provide them the level of service they expect, and you promise. 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. Keep check on your core skills and offerings, and bypass the opportunity to take on something you don’t know how to do. Nothing hurts your long-term prospects like not delivering on your promises, or delivering low quality, or late services. Your reputation for delivery is everything!
- You need to be able to be ‘alone’ – Unlike the typical career at an organization, 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 just not the same as being in a 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 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! (who knew dogs slept THIS much??)
- Discipline is key – Since I branched out on my own, I can’t tell you how many people have asked me how I’m liking 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 in my opinion. I actually have a very structured day now, which includes working out, eating breakfast, getting dressed, and being at my desk by 8-8:30 every morning. Certainly it’s not the same as having to ‘clock in’ or be at the office by 7:00 each morning, but frankly, I get up at the same time as before, but I get a lot more done first thing. If being able to sleep in, or work in your shorts all day is appealing, by all means, have at it. But, I am convinced that being disciplined will help me a lot more in the long run.
- 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 as often just wasn’t possible in the past. However, it’s more important than ever to get engaged in these organizations in my new business. Not only is this 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 to making your mark on the world in your own way!
What about you? Have you made a switch from being employed to being self-employed? What lessons did you learn that you can share? I have a long way to go, so I am eager to learn all I can!
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