Have you ever wanted to be your own boss? Did you dream of starting your own business when you were young? If you are not self-employed now, what is stopping you? Is it not the right time? The timing is never perfect, but at some point in your life, the opportunity to go it alone will surface. I’ll share some stories with you today.
Someone who made it
One of my college roommates started his own business immediately upon graduation in the mid 90s. John started an ISP company to service the college town where we lived. In those days, it took just a T3 line and a modem bank in an office at a strip mall. He did this for a few years and then branched out into ecommerce.
The company had an IPO and the stock went up for a while since anything that had the word ‘ecommerce’ attached to it was doing well in the late 90s. After the dot com bubble, the stock value dropped to almost nothing, but John continued to work on his company.
Eventually he left the start up, but the IPO process gave him an invaluable connection. He kept in touch with the venture capitalist company and subsequently became friendly with them. John then worked with the venture capitalists and helped started another company. He fully joined the capital side of the equation and this was when he hit his stride. My old college buddy is now snowboarding up in Tahoe every day and is financially independent. John is the only one I know from college who has that kind of freedom. All my other friends are working for someone else and while they are doing very well, they don’t have that kind of freedom. Guys who worked at Yahoo, Microsoft, and Cisco in the mid 90s are still working for someone now.
I’m not saying everyone who went out on their own made it rich. Other friends also partnered with John at his ISP/ecommerce company, but they eventually went to work for the big companies. A start up life is not for everyone. It wasn’t easy for John to work 80 hours/week barely making rent for years while all his friends were making good salaries, buying houses, and taking international vacations.
What about Joe?
The best time for me to go it alone was at the same time John started his own business. I did not have any student loans and my belly was full of fire. Why didn’t I join John in his venture? Unfortunately, I had to work for a big company because back then, I was an international student who needed a sponsor for the H1 visa. I needed to get my permanent residence status to stay in the US. After 5 years, I received the permanent residence status, but by then I had a house, a wife, two cars, two cats, and bills to pay. The paycheck was fat and the work was important. I actually liked my job because I was making real contributions to current and future technologies. It’s not an exaggeration to say that you probably have used a product that I helped to develop during my engineering career. A lot changed in 5 years and I became dependent on my salary and my employer. The window of opportunity to strike out on my own was closed, but it’s not permanently shuttered.
Fast forward to today. I’m still making important contributions, but now I know I am just a cog in the machine. If I leave the company tomorrow, there will be someone else to work on whatever I’m doing. I’m not willing to work long hours anymore and I care less and less about the latest version of the same product. My motivation has changed. The window of opportunity for taking off on my own is opening again.
Now, let’s look at my blogger friends who want to take the reins of their destiny, and the different phases that they are in.
Nothing to Lose – This is the time when you don’t have much to lose. This is when you are just starting out and willing to work your ass off. Corey at Passive Income to Retire fits in here. He is working on his Master’s degree while working full time job with a small salary and blogging like a mad man on his online business ventures. Personally, I think this is the best time to start a business. The major downside is the lack of capital in this phase.
Not much to lose – This is when someone has a job that is not fulfilling either mentally or financially. Kevin at Invest It Wisely recently quit his job and is planning what to do next. His pay stagnated over the last few years and the future of his company is in question. Many of his friends already left the company so he is not losing much by going out on his own. He is still in his 20s and has a lot of drive and energy. He saved up some cash and should be able to pay the rent for a while during the start up phase of his businesses. I’m sure Kevin could have gotten another job with more pay and in a year or two, it would have been much more difficult to let go of that steady paycheck.
A lot to lose – This one is the most difficult of all. Some people have a great salary, like what they do, and enjoy working with their coworkers and friends. Financial Samurai is currently struggling with this dilemma. It gets harder the more you make. He is very entrepreneurial, but can he give up all these things? Personally, I think 95% of people with entrepreneurial dreams are stuck, unable to fully pursue their dream given so much is at stake. Life is good, why give it up to work like an insomniac mad man, getting paid diddly squat?
A lot to lose, but need to go – I am in this position right now. We have a very comfortable life and leaving my day job will be an upheaval. Sure, we have been living only on Mrs. RB40’s salary and saving my paycheck for almost a year now, but it still won’t be easy to give up my six figure salary. That is a lot of money to lose, but I really have to go. I feel like this is my last opportunity to strike out on my own. I can stay at my company and do average work for 10 more years and we will continue to have a comfortable lifestyle, but at what price? I need to see if I can stand on my own and like many readers know, I don’t like the job much anymore.
To me, striking out on your own is like bungee jumping or skydiving. If you have tried either of these, you know there is a point where you have to jump or back off. The first step is the most difficult and the rest is never as quite as bad as you imagined. What about you? Have you thought about working for yourself, but the timing has never been right? When would be the right time to do it? This post is much longer than my usual and if you made it to the end, I would love to hear your thoughts.
For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.
Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.
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