Once upon a time you went to school, got a job, worked there long enough to earn some form of pension or until Social Security kicked in and you retired. Must have been nice considering by the time I was in high school Generation X was slogging through a recession where job security went away, died and never, ever came back.

People were talking about taking on part-time, freelance, consulting and contract gigs and living with their parents back in 1992. (Now known as “The Olden Days.”) In fact, there are people who lived through the 90s, had kids and now their kids are in their twenties and are in an even worse version of the economy that taught their Gen Xer parents there was no shiny happy job waiting for them post-college. How worse is it? At least all those Gen Xers had working, stable Boomer parents to pay for their college educations. What Middle Class black Gen Xers that made it saw their financial gains die out during the Bush Administration.

Everyone I know younger than me has terrible, horrible, no good student loan debt. I’m writer poor. Not student loan poor and I guarantee … there is a difference. There are lower places we can all go.

But college debt or no, all of this adds up to: Youth of today – even more on their own than the youth of 20 years ago.

Naturally, if you’re going to survive this, you’re going to have to develop a set of skills. In fact, probably a few separate but interlocking sets of skills because more than likely, you’re going to change your career trajectory one, two or 12 times. (Honestly, don’t feel bad about it. You’ll have a lot of company unless you went into some complex STEM field.) And since I’ve been battling with our Brave Not-So-New World of job instability since I left college in 1999, I’ve had to do this dance quite a bit.

Since 1999 I’ve worked as:

  • An account manager for a boutique advertisement firm
  • An education reporter for two small market newspapers
  • An editor for one small market newspaper
  • A newspaper columnist
  • A “blogger”*
  • Some sort of bootleg TV and radio personality
  • Sweater folder at Macy’s
  • Babysitter / dog wrangler
  • An senior associate for a boutique public relations firm
  • Digital Media Strategist for a non-profit
  • Freelance Journalist
  • Managing Editor of a News site
  • Digital Media Consultant
  • Ghostwriter
  • Screenwriter
  • TV Head Writer
  • Occasional public speaker
  • Editor-At-Large for this here site

Of those very random jobs I still work about six or seven of them because, I don’t know, I guess at this point I’m addicted to job titles. Also, if you have more than one job it doesn’t matter as much when you lose one of them. Don’t want me to ghostwrite for you anymore? Fine. I have six other jobs. I probably needed the extra time to focus more clearly on one of them.

While most of you will not need to have a resume that reads like a game of Random Employment Bingo, what you will need you will need to be flexible, willing to move (possibly more than you like), cultivate those overlapping sets of skills and network your little tushies off.

Here are some tips:

Become the Master of Your Particular Set of Skills: Did you study something? Have degree? Cultivate a talent and/or skill? Well, cultivate it some more because there’s no such thing as resting on your skill laurels anymore. You need to stay up on your skills. Technology is ever evolving, various careers and fields are ever evolving, therefore you too will need to evolve. This means staying up on the latest news and developments surrounding your skills/training/education, even researching online and in that thing called a “library,” joining professional organizations, going to conferences, taking courses or looking out for new opportunities to further develop your skills. It also means taking a hard look at your skills and seeing how you can market and transfer them to multiple different types of jobs, and/or into the world of consulting and being an “expert.”

Never Have Just “One” Job: Your main job is your main job, but your side job is there for you just in case your main job dumps you (as they are wont to do in this age). Again, I have six (or seven) jobs. It helps to have more than one revenue stream if you can figure out how to develop one based on your talents, background and/or expertise. Besides, sometimes that side gig can totally flip into a wonderful new full-time job that just might be the one you need to get to where you want to go in life.

Have More Than One Kind of Resume That’s Computer Friendly: Look at your skill set, now look at your resume, now look at the different types of jobs you feel you may be qualified for – then tailor each resume for that specific job field, designing it to fit the right background, skills and buzzwords of that particular career. One resume will not cut it, not in this day when rarely does a human get a gander at your resume without a keyword searching, job screening computer getting to it first. A lot of employers use this software to weed out applicants who don’t have the background they desire, but it’s a computer. It’s not perfect. You essentially need to learn how to write a resume that the computer will easily understand.

Shame and Failure – So What? Pride can keep you out of trouble, (and help you negotiate a decent-to-excellent salary) but too much of it will keep you out of some opportunities you may need to capitalize on (whether you want to or not). In this economy, setbacks are bound to happen and sometimes you’ll have to take a lump or two in order to get where you really want to go. This means there might come a time where you’ll briefly be unemployed and folding sweaters at Macy’s part-time while taking unemployment will keep you both busy and your cellphone bill paid (been there). Or your marriage might fall apart and leave you more broke than you already are (also been there). Or it might mean you’ll have to move back home or ask your friends or siblings for help (done that). It will also mean that you may have to reach out to others in your field or in the field you’d like to be in, and ask for advice on how to get out of your stagnation (thank goodness for LinkedIn). Essentially, you need to understand that it’s not wrong to ask for help and that while this year (or the last two or three years) were unpredictable and poverty-inducing doesn’t mean it will always be this way. It’s important to not lose perspective and to stay focused on the long game. Muddle through what must be muddled through until you can get back on your preferred path. Use your down time to get better, stronger and more creative.

Self-Promotion: Don’t like talking up yourself? You better learn how! Humility is great for strengthening friendships, getting right with the “Lawd” or improving familial and romantic bonds, but you need a career-boost, buddy. Now is not the time to be shy. If you’re looking for work, people need to know there’s this awesome employee out there who makes the magic happen and that employee is you. Naturally, you don’t have to turn into some obnoxious, self-involved bragging machine, but it doesn’t hurt to channel your inner Jay-Z and treat your resume like it’s “The Blueprint.” Write a bio that lists your awesome skills, your great accomplishments, your amazing talents. Get testimonials and references from past employers and colleagues who’d be willing to write letters of recommendations and polish your shine when talking you up to others.

Pack Light: If you’re going to get into the re-inventing and starting over business in order to get to your long-term career/life goal you might have to accept (or embrace) the vagabond lifestyle. This means moving quite a bit in pursuit of your greater dreams. Therefore, acquiring a ton of stuff, blowing tons of money on housing or committing yourself to one vision of who you can and should be is probably not a luxury you can afford. I’ve lived in Missouri, Illinois, Texas, California, Missouri again, Washington, D.C., New York City and Washington, D.C. again. I’ve found that if you own more stuff than you can cram into your Mazda every two-to-three years, you probably have too much stuff. Also, never be too afraid to have to temporarily rent-a-room while you search for an apartment or get a roommate. You can use that time you cohabitate with someone to save money. But also keep in mind moving (a lot) is not for everyone. Especially if you have a spouse or kids to consider, which is probably why almost everyone you know is single and delaying marriage and/or family. Those suckers take up waaaay too much space in your moderately priced fuel efficiency vehicle of rapid career climbing.

Don’t Get Married to One Version of the Future: Often we get this idea of ourselves, who we are and what we should be and become extremely disappointed when it doesn’t work out. For instance, I really, really wanted to stay writing for television, but then my show got cancelled and I was devastated. I was depressed for months. But I didn’t start out with a love for TV writing. That was a great career I came upon after several other jobs – with Web sites, with non-profits – that I “loved” went away. The reality is I’ve “really” wanted a lot of things hoping that would be the thing that would last, be stable and allow me to build. But I couldn’t afford to spend a lot of time mourning over jobs the economy ate. You may think you’ve found your one-true-career-love, but what if it goes away? You have to be able to adapt and find another career that fits. You might have to leave your field altogether. The important thing is that just because your job goes away doesn’t mean your self-worth and determination don’t go with it. You have what it takes inside of you to be the master of your destiny, but you have to believe in your skills, cultivate them, be willing to take risks and be flexible about who you are and what you might do. After all, you’re in this for the long-game. You have to play today’s workplace minefield with a long-game strategy.

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