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By Jim Emmanuel


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Working for yourself and for someone else is just plain wrong. Right?

Who in his right mind would work a full-time job and freelance simultaneously? After all, if you have a job, why freelance? If you freelance, why keep a job? Where is your commitment -- to you or your company? Working for yourself and for someone else is just plain wrong. Right?

I've been doing both, in my more-or-less right mind, for over seven years -- and the experience has been instructional. Leading a double life isn't easy, yet it was an easy decision for me. Why? Well, if all you have is a nine-to-fiver, you may have to spend eight long hours each day at the mercy of a jerk-off boss who you know is making three times the money you are. Or even worse, you might be loyal to your job only to become the zillionth victim of cost cutting and lay-offs. On the other hand, as an IP, you don't experience the security and sedating effect of a weekly paycheck, with all relevant taxes neatly withheld. One Friday you'll be feasting on filet mignon; next Friday you'll be munching on fish sticks. You may also feel locked in isolation as an IP. You're at home hunched over your lonely computer while all your corporate friends are living it up around the water cooler (you know this isn't really true, but you miss the water cooler anyway).

I know this may sound strange, but it's entirely possible to exploit the best of both worlds. The key to this approach is to freelance in the same field as the one in which you hold a job. While avoiding the pitfalls of doing either alone, working and freelancing is very liberating. What are some of the advantages?

Advantage, IP

  1. You can learn on the job. Working for someone who knows the business is the best form of training in any given field. I'm a landscape designer, and when I was fresh out of college, I wasn't at all prepared for real-world professional practice. So I viewed my first job as an apprenticeship. (For me, it was especially helpful in learning about plant characteristics and growth habits.) It's wonderful to get paid for learning -- the most profitable kind of education there is.

  2. Networking. It pays to know who the players are in your industry. And what better way to meet and greet them than as an employee for an established company? I am constantly dealing with suppliers of stone, brick, and other landscape materials. The contractors who are now some of my freelance clients are people I met at stone yards and plant nurseries. As a pure freelancer, I never would have had the volume of work necessary to frequent these places and meet these new clients.

  3. Benefits. While the biggest benefit of freelancing is being your own boss, conventional jobs offer a number of valuable perks. First, quality health insurance can be hard to come by for the freelancer (though getting insurance has recently become a bit less difficult for IPs), and some companies offer great insurance packages at relatively affordable rates. Second, paid vacations are free money to the employee-freelancer. Finally, certain employers actually offer matching funds to their retirement packages -- which is, of course, more free money. (No one, you might have noticed, offers this stuff to freelancers.)

Your job's just a big, fat freelance account. And your boss? He's just your most important client. Ultimately you only work for yourself.

Job One

A word of caution: although these advantages seem pretty straightforward, they aren't. In order to be successful, there is a very important rule you must keep in mind. It may appear that you have two jobs, but in reality, you only have one -- freelancing. The rule is this: your job is simply one big, important freelance account. Your boss is a customer of your services, one that you will truly try to keep satisfied, but ultimately you only work for yourself.

An important corollary to the above rule bears mentioning. While you know that you only work for yourself, don't ever tell anyone that you think this way. As far as they're concerned, you have a job. Or if you're known to people as a freelancer -- that's all you are. Maintaining this separation can get tricky. For instance, several times during freelance meetings, on rather warm days, I've had to conceal the company logo on my shirt by wearing a jacket. I have also accidentally made freelance calls on my company cellular phone. In any case, it's imperative that, if you go in for this kind of dual work-style, you keep your multiple personalities to yourself (except maybe to write articles about them for 1099).

However, there may be some instances in which it could be beneficial to reveal yourself. If you decide that you have a great boss and would in fact benefit from being open about your after-hours activities, downplay the extent of your operation. Make it seem like your clients are friends, or family, or friends of family. (Work your way down to distant cousins if you have to.) Make it seem like you could take it or leave it when it comes to your freelance clients, as if you're not really making a profit from them but rather honing your skills so you can better perform on the job.

Three Kinds of Crises

After entering into this life of deception, how do you handle the inevitable crises that will find you at the most inopportune times? I've experienced most of the following problems in my career as a landscape designer, but I think they apply to most careers:

  1. The "same client" crisis. This happened to me a few times. A client calls both me and my employer for design services. My employer sends me to meet with a client whom I have already seen. The client may or may not be confused over whom to hire. This crisis is solved by studying the client. I watch carefully to see if the client maintains a pleasant demeanor. In my experience, I've concluded that an easygoing customer is a good freelance customer. I once had a client, Mrs. Jones, who seemed amused by the fact that I worked for a landscaper… and had my own business. "You must be really good," she said after I handed her my company business card. "I keep getting your name." A few days after our friendly chat, she called to hire me for the job. Had she been agitated, I would have convinced her to hire the company.

  2. The "call at work" crisis. Occasionally, one of your clients may call you at work, requesting specific information. This is not really a crisis if you have a private office, but in my situation I didn't. I received a call from Mr. Freid, who wanted some detailed information about his design. I didn't have his design in front of me but I knew it inside out. I began by saying, "Hold on while I get your file." Using an unrelated file as a decoy, I discussed Mr. Freid's project without my boss knowing that Mr. Freid was my client and not his. I later told Mr. Freid to call my cell phone with any further inquiries, or to leave a message.

  3. The "where did all of my free time go?" crisis. There's a price for doing double duty, and you must be prepared to pay it. Your free time disappears. You can give yourself more free time, however, by maximizing the overlap between your job and your freelancing work. Speed is the issue. If you are doing the same sort of work in both capacities, you will become very efficient. While I spend eight to nine hours a day at the office, the three to five hours I spend freelancing yield a better return. Think of the hourly rate you would like to maintain and that will tell you if you are working fast enough. (Of course, you also need to have endurance. Working a day job and being an after hours IP requires a willingness to tough it out over a long period of time. You sign on for this kind of tour, and you'll have to ditch at least some of your leisure activities.)

Both Barrels

Can this world of apparent deception lead to a sensible and satisfying professional life? Well, let me tell you a story. I had a double major in college, philosophy and landscape architecture (I knew I wouldn't be able to make a living in philosophy). My landscape architecture classmates never knew that I was also immersed in the world of philosophy (though my philosophy classmates found it fascinating that I lived in two academic worlds). When I was in a philosophy class I often longed for a lecture on zone 5 plant material. Sometimes in a "soils" class I would yearn for a lofty discussion of British Empiricism. It turned out to be quite a rewarding combination.

The point is that there are times when your freelance accounts will be more exhilarating than your job, and times when just the opposite is true. But if you're smart, and skilled, and swift, you can use this double-barreled method to make the most of your work life.


July 31, 2000
Primary Editor: Ken Gordon
Illustrator: Steve Smallwood
Production: Fletcher Moore

We'd love to hear your comments about this article!

Jim Emmanuel is a landscape architect who lives in Swampscott, Mass. If you like, we'd be happy to put you in touch with him.


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