By: Roshawn Watson

I don’t truly understand people who say they wouldn’t change a thing in their lives if they could. While I have nothing against contentment, if given the opportunity, I would change several things not because I hate my life but to get the most out of it. If you could press rewind on your life, what would you do differently?

Start Businesses

First, I would have started businesses and have done so early. Nowadays, the barriers of entry into many businesses are lower, including smaller capital and infrastructure requirements. The advantages to owning your own business include: a) your business can be created around your passion, b) you can concentrate your efforts in your chosen areas of competence, c) you would control it and d) you would have tremendous income potential. Indeed, business owners are also five more likely to become millionaires over traditional employees, partly because the financial responsibilities of business operators corresponding well to running an economically productive household including: keeping cash reserves, decreasing unnecessary expenditures, investing for growth, watching revenues and projections, etc.

Of course, there are inherent risks too, but I would rather manage risks over eliminating them entirely. Avoiding risk altogether can be dangerous too. I additionally challenge you to redefine how you consider risk. Rabbi Daniel Lapin argues that we are all in business for ourselves. For example, if you have a traditional JOB, then you are selling your skills, services, time, and knowledge to one customer (your employer). If you are a traditional business owner, you simply endeavor to have more than one customer. This begs the question if it is riskier to have one customer (your employer) or 200 or more?

Adding a side business to your portfolio could literally revolutionize your life. For instance, one kid who grew up very poor decided to create his own video games, since his parents couldn’t afford to them. His classmates saw him playing his games, liked them, so he began to sell them copies (and then their friends). Companies took notice and had him consult on projects before he even reached puberty. Although he was being paid well, he knew that he was worth more, so he started his own company and later sold it. He first retired at 19. Then, he got bored started another business that he also sold and retired again. At the time I heard his story, he sat as a chairman of the board of directors of a publicly traded company, was a well-connected venture capitalist, and traveled the world with his team helping people replicate his success, at the ripe old age of 28!

What potential do you allow to lie dormant?

Quit More Often and More Quickly

In The Dip, Seth Godin challenged the mantra that “winners never quit, and quitters never win.” He argued that winners actually quit frequently and quit swiftly. In other words, winners find what doesn’t work and move on fast. This agrees with advice I heard 15 years ago from a businessman worth nearly a billion dollars. During the conference, he indicated that one of the most important lessons he learned was to “not kid himself. Knowing is half the battle because you can take corrective actions whereas continuing in blissful ignorance sets you up for failure.

My do over would be realizing when I am getting off course faster and to channel all my resources into moving in the right direction.

Investing Earlier and Investing More Aggressively

Does saving and investing 50-80% of your income seem reasonable to you? For most people, the answer is no. However, suppose someone showed you that if you did this for a mere 7 years, you could then retire. I thought that would get your attention. Personal finance expert Dave Ramsey always says “when you live like no one else, you can live like no one else.”

Earlier this year, I asked a simple question “How would you retire in 10 years?” The purpose of the question was to challenge the assumption that it takes a working lifetime to invest adequately for retirement. There are people who never expand their mental contexts beyond that life script who get very traditional results: they slowly build wealth, depend on social insecurity, and may have to choose between paying for some expensive medication or food. This isn’t trivial, it’s a sad reality for far too many people. Investing aggressively and early a) gives your investments a longer time to grow, b) means your source of provision is not dependent on your job, and c) expands your opportunities to reach your potential with limited financial concerns. I challenge you to be the architect of your own life. Don’t allow the complacency of good to rob you of the glory of great!

My do over would be not to allow any slack… fire on all cylinders until I was “done!”

Invest In Myself

If you are frugal (wanting to get the value for your money), it’s possible that you will agonize over things that are good for you. There are several opportunities to advance your career and improve yourself: conferences, seminars, short courses, webinars, certifications, books, but not all of them you will be free or paid for by your employer. I believe there should be at least some room in your budget to invest in yourself.

An author and entrepreneur was recently asked if he regretted wasting money on products and conferences that ultimately provided him little value. For context, he spends an unconscionable amount on educational materials each year: some are several thousands apiece. His answer was a) very few provide absolutely no value (there’s almost always something to pull away from them) b) for ever dud or two, there’s one that helps him completely knock the ball out of the park to the degree that it more than compensates for the costs of duds.

Ask yourself if you are playing it too safe with respect to investing in YOU, Inc.

Avoid Debt

We have a culture of debt: debt is the most aggressively marketed financial product. Entire industries are developed to make us think that we cannot function without debt. However, the borrower is servant to the lender. Sadly, the debtor has obligated tomorrow’s prosperity and limited his ability to build wealth, at least wealth for himself, compared to his contemporaries making the same amount without the debt. For example, if you avoided car notes altogether and invested average car payment instead from age 25-65, you would have an estimated $2,000,000.

Instead, we label debt to make it more palatable by creating trivial hierarchies of debt with all sorts of eloquent rationalizations. Sometimes this involves classifying debts as “good” or “acceptable” or an “investment.” The truth is consumer debt is consumer debt. If you are truly borrowing to invest, I hope your return is substantial, given the amount of risk you are assuming by having debt. Remember, if you have to rename the debt to overcome your misgivings, that may tell you all you need to know right there.

Early on, I would have avoided it like the plague that it is.

Carry Adequate Insurance for Key Items While Avoiding The Rest

It is often said that there is no other expense that people spend so much of their money on without understanding. No one likes insurance until they need it. We all know that insurance companies do not lose money on insurance policies. For every few people who pay a few dollars in premiums and make a big claim, you can bet they have thousands more who pay premiums and have absolutely nothing bad happen to them.

Since you can’t be certain that you won’t be the “unfortunately few” who need insurance, you should judiciously use insurance policies to transfer risks in key areas. After learning this, my whole perspective changed. For example, many people are surprised that I don’t carry an insurance policy on my cellphone. However, cell phone insurance policies tend to be pure profit for the phone companies. My bet is if I replace my phone every 2 years (or so) and make sure that I get a phone that is highly rated, I do not need to pay an extra $120/contract for insurance given: a) the phone’s under warranty anyway, b) I’m not very rough (and don’t lose) my phone, c) and I could cover the cost of another phone within my budget. I also do the same thing for extended warranties (functionally they are insurance): did you know that they often represent a 50% margin, which is almost pure profit. Consider, how much could be saved by carefully analyzing our insurance needs.

My do over would be maintaining adequate coverage for the sensible things at all times and avoiding all others like the financial drains they are.

Is The Struggle Necessary?

Pain is definitely a teacher. It signals that something is wrong, so problems don’t persist undetected. However, learning from pain is also slow and unpleasant. If I was designing my life, I would obtain pearls of wisdom from others experiences via mentorship over learning from my own mistakes. Personally, I would rather someone tell me how dangerous it is to ride without seat belts than learn from first-hand experience.

Well, yesterday is over, and tomorrow is not yet here. However, if you could press rewind on your life, what would you do differently?

Lastly, if you like this article, please subscribe to my FREE email updates or RSS feed (reader), Retweet it, Like It on Facebook, Tipd it, Fark it, Stumble it, and tag it on Delicious. Also, click here to receive my eBook for FREE.

Related Posts

Young People Avoiding Investing In Record Numbers

Labeling Debt To Make It More Palatable

How would you retire in 10 years?

Money Down the Toilet for Security