The classic midlife crisis was always associated with success: the sports car, the fancy clothes, the inappropriate girlfriend, but not anymore. That’s so Mad Men. Today’s midlife crisis involves getting laid off at age 46 and having your well-meaning friends suggest that you get a pink Lyft moustache for your aging, still-not-paid-off car as a way to earn gas money. Related: Career Transition For Middle-Aged Professionals Why does the Don Draper midlife crisis seem so ironic and dated? It appears laughable today because American midlife and mid-career have changed so radically in the last few years that it’s darkly amusing to think of what might have been for us. I’m not endorsing inappropriate behavior. I’m just pointing out that, until perhaps ten years ago, the achievable ideal of midlife and mid-career for most educated Americans was one of privilege, success, and affluence. If you wanted it and worked hard for it, you got it. You got the job, the salary, the benefits, the long-term employment commitment, all of the goodies. Not today. Not by a long shot. What happened? How did the mid-career success that looked so attainable when we were in our 20s become such an illusory mirage, a mean-spirited joke that is hammering our generation into a place of fear and stress? A lot has happened, it turns out, much of which probably could not have been avoided or predicted. But, it happened nonetheless. The Cold War ended. The rise of China happened. The Internet happened. The tech wreck of 2002 happened. The financial crisis of 2008 happened. The breakdown in corporate governance happened. If I had told you, in 1989, that over the next 25 years, China would overtake Japan as the world’s second largest economy, the USSR would disintegrate - causing a big reduction in the well-paying defense industry, that new technologies would enable real time white and blue collar collaboration anywhere in the world – enabling a vast shrinkage of the American employment base, that financial disruptions would flatten retirement savings schemes twice, that CEOs would face virtually no accountability or consequences for bad decisions and be able to enrich themselves dramatically without any reciprocal loyalty to employees – you would have thought I was either crazy or exaggerating. But, that’s essentially what’s happened. That’s the bad part of our new midlife crisis. It was forced on us. At least in the Don Draper days, if you wanted to act out, you had the freedom of choice. Skipping today’s crisis is not an option. It’s a very disempowering notion, disturbing perhaps, but think about it: Am I wrong? Surely, the reality is somewhat different for each of us. (I know. Stop calling me “Shirley.”) It’s not as if every American over 40 is desperate and in trouble. However, I think most people would agree that the risks of career instability and financial reversals are far greater than they were a generation ago, that the potential to get and hold onto a long-term high earning position have been significantly degraded. How secure do you feel about retirement? If you’re not worried, you’re not really paying enough attention. We’ve been disempowered as a generation. This is troubling. Yet, we do not need to be victims. I truly believe that we can achieve financial security, success, and satisfaction with our working lives. To get there, though, we need to rethink what it means to work. Getting empowered means discovering where we add value in the business world and executing a personal strategy for extracting that value from corporations. In a lot of cases, this is not going to involve having an actual salary-paying job. Jobs these days for people over forty are a bit harder to find than they used to be and their long term prospects are not as secure as anything we might have imagined a generation ago. I think self-employment is going to be our ticket out of midlife disempowerment, out of our unwanted midlife crisis. What does self-employment look like for you? You have more options than you realize. Maybe the whole idea frightens you to death. I understand. But, if you look at the alternatives, the idea of supporting yourself through your own initiative and value creation might start to look at lot more appetizing. Are you ready to empower yourself in midlife? Let’s start the journey. This post was originally published at an earlier date.

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This post is part of the Professional Independence Project series. If you’re old enough to know what a memo is, you’re old enough to get this one. The “Gig Economy” is here. In the gig economy, you make a living with short term freelance projects, or “gigs,” rather than a traditional job. Examples include ride sharing services such as Uber, and freelance web hubs like Fiverr and PeoplePerHour. Related: 4 Ways To Get More Freelance Work For many young people, it’s entirely normal. For those of us a little further along, it’s seems a bit suspicious or even disreputable. Boosters like to say that it is reinventing the workplace and adding to our freedoms. Detractors warn that gig economy income is unreliable and that it costs workers many rights and benefits that they have long enjoyed in the workplace. Well, here’s the rest of the memo: Whether or not you’re in favor of the gig economy, you’re already in it, even if you have a regular job. The new reality in the American workplace is that, for many of us, what was once known as a full-time job is actually a gig, a year or two-long assignment that will end with you being renewed or kicked out. As we get older, the process of getting kicked out becomes more and more painful. Reentry into this high-turnover, low-loyalty workforce becomes more difficult. As a result, doing gigs emerges as a viable career option for many of us. My own experience can be illustrative. After fifteen years of serving as a marketing executive at technology companies large and small, I went off on my own a year and a half ago. I am now a freelance writer of marketing content. So far, it’s gone pretty well, but I’m constantly looking for ways to make it better. In the spirit of learning and open-mindedness, I found myself signing up for a Fiverr account a few months ago. I told members there that I would write them a press release for just $5, of which I would get $3.92 after their cut and a PayPal fee. Was I out of my mind? I make six figures writing marketing content for Fortune 500 corporations. Why on earth would I write a press release for $3.92? Yet, my decision to try it represents one of the basic principles of the gig economy, which is that you always have to be willing to experiment and see what you can learn. The gig economy is not static. For those of us over 40, we need to work harder at figuring out where it’s headed. What did I learn? I learned something that I already knew, which was that $3.92 is not enough money for me to write a press release. But, I also learned that it was possible to strip the process down to the point where I could turn around five dollars’ worth of press release in about 15 minutes. If I were 22 and hanging around a Starbucks, that would mean I would be hauling in about $16 an hour – more than the Barista makes. With rush charges and add-ons, you can make more, but it still wouldn’t be a living for me. Yet, I’m glad I did it. I highly recommend trying an experiment with the gig economy, if for no other reason than to understand what you’re competing against. If you run a PR firm that charges clients $25,000 a month, it might be educational to see what people can get for $5 on a gig economy site. With that in mind, let me share five thoughts on how to have a successful gig economy experience:
  1. Don’t get caught in a race to the bottom – Competition from gig seekers puts pressure on us to find out where we really add value.
  2. Use it to learn about yourself – The gig marketplace can provide us with insights about what we are actually good at and enjoy doing.
  3. Use it to test entrepreneurial ideas – The gig economy doesn’t penalize failure because, a la Fiverr, if you fail, you’re out less than four bucks. It’s a great place to try new ideas.
  4. Be organized – You’re the CEO of your own business in the gig economy. This is good news for us older workers. We can bring decades of discipline and management skill to the task of getting and completing gigs.
  5. Think like a salesperson – Gigging means constantly selling yourself. This might sound stressful but the good news is that you’re selling bite-sized bits of your time. It’s a low pressure sell, a low stakes game where both sides benefit from the transaction.
Gigging can even be fun. You can get lots of positive feedback about your work, an experience that can be rare in the regular workplace. Go for it!

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