Freelance Endgame: 5 smart moves for “retirement”

December 8, 2011 by Dean Rieck
Filed under: Freelancing 

freelance retirementSo. Where do you see yourself in 10 years?

I know that sounds like one of those nightmare job interview questions, but it’s worth asking yourself.

Where do you see yourself in 10 years? 20 years? 30 years? What’s the endgame for your freelance career?

To me, freelancing is a little like playing chess. That’s because for both there are three distinct stages: the opening, the middle game, and the endgame.

You see, when I was younger, I studied chess. Yes, I was a nerd and actually “studied” chess. That meant working my way through dense books full of difficult and arcane chess strategy, including how to handle each stage of the game.

The opening is all about rapidly deploying your assets to put yourself in a strong position and maximize your future opportunities.

In the middle game, you develop your position, trying to avoid costly mistakes and pursue rewarding opportunities as they arise.

When you get to the endgame, you narrow your focus to achieve your goal. The result depends entirely on all the previous moves you’ve made.

If you’re just starting out, you may not want to think that far ahead. And you certainly can’t plan for every possibility. Life is far more random than chess, after all.

But you should have some idea about where you’re headed and the goal you’re chasing. You can’t achieve it if you don’t know what it is. Right?

Here are 5 possible endgames for freelancers:

Plan to retire. You work hard, build your business, and save your money. When the time comes, you’ll be able to step away and relax. Maybe you want a comfortable beach house in Florida. Perhaps you want to travel or indulge in your hobbies. Nothing surprising with this goal. This is what most people want, whether you’re freelance or a full-time employee.

Get a job. Few people who talk about freelancing mention this possibility, probably because those who get into freelancing are often trying to escape employment. However, this endgame makes a lot of sense. Freelancing can bring you close to a lot of employers and open doors that ordinary interviews and resume mailings can’t. I’ve been offered countless jobs over the years.

Grow your business. Those with an entrepreneurial streak can use what they learn at freelancing to turn a small business into a bigger business. You can create and sell products online, start up a consulting firm, use your writing skills to open a brick and mortar business, or pursue a joint venture with another freelancer with complementary skills.

Turn full-time consultant. Unless you’re a writing machine, freelancing can become taxing after a few years. It’s hard work. But if you gain expertise in a particular field, you’ll find that some clients want your knowledge as much or more than they want your writing services. Sharing advice can be much easier and often pay better than writing.

Keep on truckin’. And then there’s the possibility that you could just keep doing what you’re doing. Maybe you scale things back, get a little more choosey about your clients, or focus your time exclusively on projects that interest you. After all, if you like to write, there’s no age-limit. As long as your mind is sharp, you can write forever.

Which is the best endgame? That’s up to you.

I’ve always planned to just keep on truckin’. But you never know what the future holds. As they say, life is what happens when you’re busy making other plans. So think about where you want to go, but be willing to go with the flow. Freelancing can take you to wonderful places.

How about you? What’s your endgame?

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  3. Admit it. Why do you really freelance?

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