5 Unconventional Do-Over Approaches to Career, Business, and Life

Recently I wrote about 14 things I wish I could have told myself at 25. Popular post, lots of people emailed their thoughts, so let's go a little deeper.

Here are five different approaches to education, jobs, career, and business that, if I could go back, I would handle differently:

1. Education. I went to James Madison University, a four-year school. I paid my way through by working at a local manufacturing plant. (Which, since often our professions are like an arranged marriage, certainly set the stage for my first career nuptials.) I defaulted into the communication arts program mainly because I didn't have a clue about what I wanted to do.

If I had it to do over again, I would:

• Wait a year to start college. But not backpacking through Europe. I would work instead. I would have learned a little about the real world, since college is anything but, and at least figured out some of the things I didn't want to do. (Except in certain circumstances, waiting a year can be a smart move for many kids.)
• Spend the first two years at a community college. In Virginia the state schools have formal arrangements with community colleges; for example, a student who gets a 2-year degree and at least a 3.4 GPA is guaranteed admission to the University of Virginia. When I graduated high school UVA didn't want me; under this system they would been forced to want me. In community college I would have saved money on all the classes I didn't pay attention to anyway, and eventually I would have received a degree from a prestigious school. (Not that there's anything wrong with JMU.) I can't think of a good reason not to take this approach; feel free to explain why if you disagree.
• Get a degree in a "profession." In terms of jobs, my comm arts degree qualified me for, well, nothing. The same is true for lots of other degrees; unless you plan to teach or go on to graduate programs, to most employers your English degree is a generic, interchangeable degree. If you're thinking business, get a finance degree rather than a business degree -- you can always be an accountant or analyst. Or get a nursing degree instead of a biology degree. If, say, you don't end up working in finance, no problem; your finance degree is just as good as a liberal arts degree to the average employer.

If I had it to do over again, I would first get a job outside my chosen field. Say you earn an engineering degree; instead of being in a hurry to land a job calculating structural loads, work for a construction company for a year or so. Or if you get a finance degree, work in retail. Think of yourself as a conglomerate that chooses to integrate horizontally. The skills you bring from your "outside" experience will make you better at what you choose to do and differentiate you from your peers. You have 40 years to calculate structural loads; there's no rush.

3. Career. Until I left I was convinced I would spend my entire career at Donnelley. Why work anywhere else? Big company, good pay, good benefits, good opportunities... only when I was gone did I realize there were lots of other great places to work.

If I had it to do over again, I would create a series of 10-year plans. My goal would be to "milk" the Donnelley experience for everything it was worth while preparing myself for my second 10-year career. Around year five I would decide what I wanted to do next and start getting the education, experience, and skills required to make the transition. If after 10 years the grass wasn't greener, I would still have choices -- choices I got to make rather than choices that would only be made for me. Think of your working life as a four- or five-act play and write your own script.

4. Small business. The thought of starting my own business was... heck, I never thought about it for around 20 years.

If I had it to do over again, I would start a small side business within the first couple years of graduating college. (Or if you don't go to college, within the first couple years of starting your first job.) Start any business, preferably in a field far removed from your industry or profession. It's easy; you can start a business in one day. Entrepreneurial skills benefit every career, and who knows -- your small business could turn into a full-time venture. And if you currently own a small business, great; start up something different on the side because the same principle applies.

5. Personal achievements. For years I worked and raised a family. No regrets there... but I do look back and wish I had used some of my spare time more wisely. I don't speak a second language, can't play piano, never hiked the Appalachian Trail...

If I had it to do over again, I would set meaningful personal goals and pursue them as actively as career and business goals. I regret wasting hours on TV, or Web surfing, or just being lazy that I could have spent learning something new or achieving a cool goal. In most cases, mastering a skill is fairly easy as long as you take the right approach. Say you've always wanted to write a novel; think how far along you would be if you had actually gotten started and kept plugging away. Starting something new is always difficult, but regretting is infinitely more painful.

What about you? What different paths would you take?

Related:

• Are You Smart or Clever? Here's How to Be Both
• The Stealth Approach to Achieving Big Goals
• Best Tip for High School Grads: Don't Go to College Yet