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Transition Your 9 to 5 Job to a Work Anytime & Anywhere Job

Written by Jared on March 20, 2011

Meeting in an office not telecommutingThe hardest part of becoming a location independent professional is finding or establishing a source of income that can be earned remotely. For those with day jobs, the best path may be to transition your existing job to a telecommuting position.

Transitioning to a remote workplace can be done with varying degrees of success, depending on the specifics of your situation and what you wish to achieve. There is no magic solution. And it can be a lot of work.

Let’s be realistic, not all jobs can be done remotely, let alone completely location independent. But who knows, maybe in the process of trying you find that your skill set provides other opportunities to achieve your goals.

Consider Reality

  • Can your current job be done off site? If not, are there other jobs in your career path that can be done remotely?
  • Do you or any of your colleagues currently work from home?
  • Have you built a relationship of trust and mutual satisfaction with your current employer?
  • Is telecommuting for you? Are you disciplined enough to work with minimal supervision in a distracting environment? Do you have proven time management skills?

The good:

  • If you have worked from home, or have colleagues who telecommute, your employer is at least open to the idea of remote work.
  • If you have worked at least six months at your current position, than you have had time to build trust and demonstrate your work ethic to your employer. A positive performance record can open the door for negotiations.
  • If you have experience working remotely in a potentially distracting environment, you’ve had the opportunity to demonstrate your discipline, work ethic and reliability.

The bad:

  • If your job can’t be done remotely, consider looking for other telecommuting jobs that use your current skill set, possibly with the same employer. Also consider finding freelance or temporary work that can be done off site, building a base of clients for future work.
  • If you are inexperienced in your career, or with your current employer, you will have a more difficult time negotiating a change to your work environment. Consider ways to build experience, trust and demonstrate that you’re a reliable, hard worker.
  • If you have a hard time focusing, are easily distracted, or have difficulty dealing with changes to your work environment you will have to work extra hard to perform your job remotely.

Make a Plan

Having a detailed and reasonable proposal that you can articulate well to your employer is crucial to your success. Start by coming up with a list of your goals and expectations. Aim small and continue to build toward your long term goals as you achieve short term success.

Creating a telecommuting proposal is similar to writing a resume. Concentrate on what you bring to the table and how it will benefit your employer. Avoid discussing how the arrangement will benefit you personally, but be prepared to answer questions.

As opposed to writing a resume, you have the advantage of specific experience. Prove your plan by demonstrating what you’ve learned. Give meaningful examples of past work experiences that show you are reliable and successful.

Factor your experience and level of trust with your employer into your plan. If you are new to the job, you may need to put in more time first. You can try to do this in conjunction with other short term telecommuting goals. Just keep in mind that an established relationship with your employer is the best negotiating point you have. You shouldn’t play that card before you have something significant to gain.

Ideas for your proposal:

  • Write your plan down. Be professional, treat it as a contract between yourself and your employer.
  • Consider supplementing a written plan with a presentation when first proposing the idea to your boss. He/she’ll be able to understand and respond to a presentation more immediately than a written document.
  • Explain how telecommuting will benefit your employer. How will it make you more effective at your job? How can it save your employer money?
  • Outline your job responsibilities and illustrate how you will continue to fulfill them while working off site.
  • Highlight successes from your work experience that demonstrate you’d be an effective telecommuter.
  • Clearly define your employer’s expectations. Show how you will remain accountable and connected to your work place. Offer daily reports, or other communication measures that allow your employer to stay informed of your work and contact you if needed.
  • Propose a written schedule. Offer clear dates and times that you are willing to work remotely. Explain where you will be, how you can be contacted and what you’ll be doing.
  • Show that you’re flexible. The biggest reason to telecommute is the added flexibility to your lifestyle. Explain to your employer why this flexibility will be good for them.
  • Offer sacrifices. Telecommuting makes life easier for you, offer ways to make it easier for your employer. If need be, offer to take a pay cut. Figure out how much money you would save by not going into work every day. Then put a price tag on your freedom to be anywhere while you work.
  • Propose trial runs. Give your boss an easy out, show that there’s little risk in letting you prove that your plan will work.
  • Be open to changes. Explain how you’ll revise the proposal to deal with any concerns raised by your employer after you start telecommuting.

Start Small

Location independence can’t be achieved in a single step. Transitioning a job to a telecommuting position requires incremental steps that should be detailed in your proposal. How you plan your steps depends on your specific circumstances and your personal goals. What do you want to achieve, and how much time are you willing to spend to get it?

Assuming your final goal is location independence, here are some of the small steps you can take to get there:

  • Reduce your office presence. Work down the hall or from the coffee shop around the corner. Stay on site, but do what you can to work away from your desk.
  • Work from home. Pick one day out of the week, make it work, then ask for more days.
  • Volunteer for projects that can be done remotely.
  • Offer to take on extra work provided you be allowed to work remotely.
  • Coordinate your off site work to maximize the time you can spend remotely. Pick specific projects, or periods of low workload to make it easier to transition to spending more time out of the office.
  • Minimize events that force you to be on site. Do all that you can to not have to be in the office for unexpected or uncontrollable reasons.
  • Introduce new tools. Work with your colleagues and boss to introduce communication and project management tools that allow you to work more effectively.
  • Work and travel. Take a trip for fun, bring some work and see how it goes. Again, start small!
  • Re-evaluate your proposal. Once you take a few steps, go back to your plan and see if you’re still on target.
  • Talk to your boss about your progress. Discuss your successes and concerns and make sure that expectations are being met.
  • Ask for opinions from people you care about. Talk to your colleagues, family and friends to get a feel for how they view your telecommuting progress.

The more work you do away from the office, the easier it will become to increase the amount of time you work remotely. Much like being hired for a new job: the hard part is getting your foot in the door!

Negotiate With Your Employer

Leverage your existing relationship with your employer. Use what you know about your boss and your job to decide how and when to begin negotiations.

Treat negotiations as you would a job interview. The more prepared you appear to be, the more amicable your boss will be. Cover all of the angles. Think of questions or concerns your boss might raise and how you will respond. Include solutions to the most common and relevant concerns in your written proposal and refer to them during the negotiation.

Common employer concerns are:

  • How will I know you’re doing work?
  • How can I be sure you’ll stay engaged with the company’s business processes?
  • What if I need you in case of an emergency?
  • How can I be sure you’ll keep the company’s sensitive information secure?
  • If I let you work remotely, I’ll have to let everyone do it.
  • How will you manage the equipment you need to do your job?

Lay out your plan clearly and concisely. Keep it short and sweet and gauge your boss’s reaction before diving into any details. Don’t overextend yourself, pick a starting goal and consider your negotiations a success when you’ve achieved it. Don’t try to get everything you want right away. Renegotiation will be much easier once you have proven your ability as a telecommuter.

Talking to a human resources representative before approaching your boss may be worthwhile, if you have the opportunity. HR will be able to explain company policies on telecommuting. Even better, they may be able to point you to other employees who telecommute at your company. If you are lucky enough to have telecommuting colleagues, get as much information from them as possible before you face your boss.

The more feedback and practice you get before approaching your boss, the more prepared you’ll be. Practice by explaining your proposal to friends or colleagues. Not only will this help smooth out your delivery, the questions and ideas proposed by others will help you revise your plan and think of responses to concerns your boss may have.

Be prepared to be rejected, at least partially. Consider why you could be turned down, and be ready to address these concerns. Offer to make sacrifices and propose risk-free alternatives that will at least allow you to prove your case. If all else fails, start looking for a new job!


#1 grace 2012-02-28 00:48
In order for you to really succeed is to have a plan, a very good and strategic plan. I like what you wrote here, it's very informative and thank you so much. I came across a video that talks about the how-to transition from your day job to your dream business from Marie Forleo.

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