In Search of Success & Freedom

I have written on the topic of personal freedom many times. Since my early 20’s, my ultimate goal has been to work toward achieving freedom from the regular things that end up tying us down. I have had success and failure along the way through my efforts to achieve personal freedom and have learned a lot along the way. We moved across town this weekend and through that process, I spent a lot of time in the car with my father-in-law. We discussed work and life, which ultimately led to a discussion of basic life securities.

My father-in-law is a hard worker. He recently retired from many years of service to the same company. Though he is not old, or quite at retirement age to draw from social security, it was time for him to move on. Being that he and I are from exact opposite ends of the workforce spectrum, we occasionally discuss the topic of work and all that comes with it. Though he does not have any direct experience as a business owner, he recognizes the role differences between his jobs and my job.

Over the years, I have received job offers, usually from clients I have worked with. There have been a few years where business was slow and I actually looked around at what was available. I have never entertained anything to this point, but sometimes the concept most people refer to as “job security” is fun to fantasize about.

During our discussion, he brought up a few of my complaints I have had over the years such as rising healthcare costs for my family, taxes, and the challenges the self-employed have purchasing a home since the housing market crash. That led to discussing the various job offers I have received over the years. To most, the solution to my “first-world-business-owner-problems” would be to get a job where I had health benefits and a w2. I understand that perspective. Beyond that, most people would assume that a business owner can’t just turn off the work mindset at the end of the day. Society typically portrays business owners one of two ways:

1. The Tyrant: This is the business owner who sits in his office all day counting money as his employees slave away for low pay.
2. The Founder: This business owner works near 24/7 giving themselves little sleep and even less time to their family.

Through the many conversations I have had with people, most see business owners as one or the other. Media and the startup business community considers long hours as a requirement for being successful. There are popular online personalities such as Gary Vaynerchuk and Casey Neistat who broadcast a perceived lifestyle of working 14+ hour days. Whether that is the case or not, that simply is not healthy and should not be honored as a lifestyle to follow in the footsteps of.

If you are going to own or start a business, the mindset is that you are going to have to work extremely hard up front, in order to have success later. This makes sense as it’s the only way most people can wrap their head around rising to success. Before I talk about success to much more, I want to be clear that success means something different to everybody. My definition of success is different than yours, and that is ok. Besides being a business owner, I am a husband and father to three children. I see my wife and children as my most cherished worldly possessions, so that is the lens in which I focus my life through.

I want to be able to exist with the basic comforts we expect to have here in the United States. I need a home in a safe neighborhood with walls that has heating and air conditioning. I need a reliable vehicle and food to eat. I need clothing that is in decent condition and a few dollars left over to buy the occasional piece of technology. What I do not need is excess. I did excess for a couple of years in my early 20’s and it did not lead to happiness or contentment. At age 24, I was making more money than I have ever made to date with my retail business, but I was spending all of it. I was also working long hours. I have discussed this before in other posts.

My definition of success has changed over the years. It used to be all about money. I was a kid and had no real concept of what contentment was. My current definition of success is to be able to provide a decent life for my wife and children. Not a life where they get whatever they want, but a life where I can provide basic comforts and securities, without going overboard. I have been blessed with the ability to do that so far.

My definition of total personal freedom will also change, but right now the definition and goal is to one day be able to self-sustain financially. That means that the work I have done so far is producing enough income to cover our life expenses for a while without having to do more work. Some call this retirement, but I don’t really like the definition most people give retirement. Most people see retirement as the end of the line where they do not have to work or use their brain for much anymore. I plan to follow in my Grandmother’s footsteps and use my brain to the best of its ability until I take my final breath. Of course, I could work extra hard now in order to obtain self-sustainability much earlier, but at what cost?

It is important to have a clearly defined understanding of what being successful means to you. If you do not have that understanding, you will never reach a level of success you can feel comfortable with. I know plenty of people who make more money than I do and even more who have a dual income household. I know people who work twice as many hours as I do, and I know people who barely work what would be considered part-time, yet still make more money than I do. None of that affects how I feel about what I have or haven’t achieved yet in life.

It is easy to think that if I just worked two more hours each day, I could take an extra vacation or afford to have a bigger house, but what would that do to my freedom? I am not the best at it, but I try to weigh each decision I make that requires my time against what it would cost my family. That puts things into perspective quickly. I see time away from my family as a deficit regardless of what the result of that time produces.

Getting a job with a company would not necessarily make me feel any more secure or provide me with any additional freedoms. Having paid vacation might make it easier to take one vacation, but if you set it up right, owning your own business gives you the flexibility to take multiple vacations and occasionally work from them if need be. It’s getting harder to do that now that I have kids in school, but we still try. The photo above was taken a few years ago when we went to Del Mar on vacation. I worked while our kids napped and we spent the rest of the time at the beach (Look how chubby Cohen was!!).

For me, reaching total freedom does not mean never having to work again. That would actually be torture. My brain does not operate that way as I am always trying to solve problems and come up with solutions. Beyond that, I never tire of learning about new things. Whether I am working for myself, someone else, or in partnership with someone else, all must align with my defined goals of freedom and success. Anything short of that would lead to confusion and frustration.

The reality of it is that there is no true freedom from everything. We will always have obligations and requirements. People will always expect something from us. However, if you have a personalized definition of what freedom is to you and what being successful is, you will more easily be able to obtain it. As a side effect, you will also prevent the endless chase that comes from nothing ever being enough.

What would your definition of a successful person be? Are you working toward reaching that level of success? What do you consider “true freedom” to be? Are you working toward reaching that level of freedom?