The Hired Guns Blog

On Wednesday, May 25, David Holloway will be teaching a Hired Guns Academy class on How to Develop a Portfolio Career. Below he explains what you gain by using this approach in today’s highly disrupted and unpredictable workplace.

Just about all of us have felt threatened, insecure or challenged in our career in recent years. The sort of niggling feeling that you can’t just set and forget your job; the feeling that it might all go wrong if you don’t handle things with care.

Global financial crisis? Tsunami? Things that will pass in time?

Sorry, no.

This is the world we are all in now. It used to be the case that one set of skills, one career, even just one company, was enough cake for a nice long career and a soft landing at the end of it. When that cake was iced with the safety of a 401(k), social security, and the proverbial gold watch when you retired, most people found that they had enough financial security to be well off throughout their lives.

But the mother ship has flown away. In its place we have the permanent white water of work and the uncertainty of constant flux: there are rapid business cycles, disruptive technology, globalization, outsourcing, telecommuting and relentless organizational change and restructuring. It has been said that people nowadays go through seven careers in a lifetime. But that number seems to be reached solely through anecdotal evidence (and it feels high), so let’s halve it. At a minimum, therefore, you are likely to need enough skills to give you at least three careers. You will also need extensive networking abilities and a very thick skin, and you’ll probably have to do quite a bit of moonlighting. And that still might not be enough to feel safe.

Some see this as a threat, and they try to hold back the water. Others, like Timothy Ferriss, the author of The 4-Hour Workweek, realize that the changes are coming, ready or not, and are trying to turn them into opportunities for greater freedom, wealth, and self-expression.

There’s no getting away from change. So do you want to try to take shelter in the house while the big bad wolf tries to blow it down, or do you want to learn to live out in the wild? Do you want to be on the train, or do you want the train to run you down?

Here’s a dirty little secret for you: the future of income and wealth is portfolio management. In the future, your income isn’t likely to come from just one job that someone else provides to you. It will come from a series of different services, products, and/or investments–all of which you will have to conceive and orchestrate yourself. But if you can do that right, you will never have to worry about losing your “job” again. You will be able to blend your creative, philanthropic, and personal passions with your work. And you will truly be CEO of your own career.

A portfolio career is a carefully organized set of independent income streams. I say “income streams” to include products and investments as well as services. Some commentators suggest that it’s merely a set of part-time jobs to replace a full-time one, but that is a narrow view, and there is so much more you can do. Done correctly, a portfolio career is the starting point on the journey to career independence and a way for you to fully utilize your skills and experience. Of all the options available to people who have decided to leave the world of full-time work, it’s the fastest and easiest to start and also the most flexible. It also embraces, rather than denies, the change and disruption going on around us.

So if you want to take this path, what do you do? How do you get started? Here are a few tips:

• Will it work for you? Not everybody is cut from the right cloth for this approach to work. It’s best for those who consider themselves generalists. You will at the very least need a variety of skills, a very good network, and lots of personal drive and resilience. Make sure you are really up for it.
• Start with a solid base. Those who succeed best in portfolio careers have planned for them carefully and start off with a stable foundation–and that includes a solid financial foundation. It also helps a lot to be very clear on what your primary service is. It’s ideal if you can start with an anchor client in one area and build from there, with a clear vision for how to expand your service offering and client base.
• Plan short-term; dream long-term. A basic portfolio career is service based; initially, at least, you make your income from a mixture of different services. But the people who really get the upside from this are those who have a plan to use the white space in their work world to do other things. They see a way to move, over time, toward passive income streams from products or investments, while maintaining the strongest and most lucrative service income streams.

As you can probably tell, I can talk a lot more about this topic. That’s just what I’ll be doing in my class. In this course you will learn:

• What a portfolio career is and how compares to other alternatives to full-time careers
• What it takes to successfully embark on such an approach
• How to generate a service-based portfolio career that flows from your existing skills and experience and that has synergy
• How to move from a service-based portfolio career to a equity-based model of investments and products and passive income.

I hope to see you at my Portfolio Career class on May 25th–register here.

[Photo: "Highway Post Office Clerks at Work," Smithsonian Institution/flickr]