Exit Strategy 1: Work Forever

I have decided to start my exit strategy guide with my least favorite of them all: either working until you are too feeble to continue or until you get so frustrated that you quit and seek alternate work.

At first glance, this really looks like a horrible plan. It also seems like the option too many freelancers use, if only by default or a lack of planning. Granted, you may have a savings account or wisely invested funds from your successful years as a freelancer, but unless you made plans to create self-employed 401k or you are a master of the stock market, these funds might not be enough to buy you that vacation home in Belize and still cover the cost of your medication.

Build an Empire

For other types of small businesses, working until you decide to work no more can actually be a viable plan (albeit not necessarily the smartest one). By virtue of building a business for 20 or 30 years, most small businesses develop some kind of empire. They may have a restaurant or storefront with inventory, a brand, tens of thousands of dollars worth of equipment – all the kinds of stuff that can be sold to someone interested in buying the business from you for a pretty penny.

Most freelancers don’t have this luxury, unless you can find someone who is willing to buy your client contact list for enough to pave your way to a beachside resort. And although some freelancers do build businesses with employees and a strong brand, this is most decidedly the exception to the rule.

Love the Work

However, there is an upside to simply working forever. We’re freelancers. We work from home, almost completely avoiding the exhausting routine of getting dressed for corporate jobs, commuting to an office, and working for someone else. Most of us do what we do because we love it. A lot of successful authors and Hollywood icons continue working well into their retirement years. We have to assume that they have enough money that working isn’t a necessity; therefore, they must have some desire to keep the work going strong simply by virtue of enjoying the work.

Become so Successful You’re Worth a Fortune

I have not even been a freelancer for a year, and the prices and jobs I now get are substantially greater than those I got in the beginning. From what I hear and what I read, this upward spiral will only continue to go in that deliciously vertical direction. As we freelancers age and continue doing this work, we can only become more specialized, acquire more high-quality (read: high-paying) clients, and become more selective in our choices of jobs. This lends itself to a pretty bright future.

Ideally, freelancers should be able to build themselves up for 20 or 30 years and then reduce their workloads but still command adequate prices. Or possibly even hire and train someone to do all the hard work of finding and communicating with clients (kind of like an agent), while you simply lend your style and byline. In either case, there is no reason why you can’t live in your cushy Arizona resort playing golf every day - as long as you are okay with setting some time aside each week to work.

Maybe Not

Of course, this isn’t a theory I have personally tested, but it makes sense. The only uncontrollable factor is being good enough and specialized enough to eventually command those high prices, which can actually be a pretty big gamble if you aren’t seeing a consistently upward trend as the years progress.

Although I do think this could be done with the right amount of luck, fortitude, and love of the work, I would probably combine the benefits of working until you don’t feel like working anymore with a nice, solid financial plan. Which we’ll get to next week.