Transitioning From Employee To Stay At Home Entrepreneur

by / ⠀Startup Advice / January 5, 2013

The single most important factor in successfully switching from full-time employment to a home based entrepreneur is not starving to death. After that comes staying warm and dry, and truthfully, becoming financially secure.

But during the transition you will be faced with hurdles and priorities that can present opportunities to fall on your face and/or bolster your chances of staying home for the long-term.  The typical tax and health insurance issues and information can be found nearly everywhere.  But did you know there are many other factors to leaving your commuter job and having a successful stay at home career?  The following is my personally filtered, hard-earned list of some of those hurdles and priorities, in no particular order.

Bite Your Tongue

Leaving an unfulfilling full-time job is so satisfying that the urge to burn your bridges can sometimes be irresistible. Nevertheless, I urge you to avoid, if you can, the temptation to depart with a boisterous “so long, suckers!” and squeal your tires leaving the parking lot.

A clean break may appeal to those transitioning from full-time, away-from-home employment to their stay-at-home jobs but it’s rarely a good idea. Setting aside the fact that leaving behind a friendly reputation is just, you know, mature.  Your former colleagues should be an important part of your new network. Furthermore there may be a way in which you can frame your relationship with a former employer that can buttress your transition to working from home. Once your employer knows that you’re serious about leaving they may become more amenable to something you should have already approached them about — remote working.

If they’re up for it, it’ll probably be after you’ve accepted a salary decrease. Fair enough. But the upside for you is the fact this will allow you to retain a consistent income while steadying your home business. You get to work in your pajamas and you’ll be saving a tidy sum on gas money.  On the other hand, remember to approach this negotiation as you would with any other client offering and don’t settle for less than you’re worth. Above all do not negotiate any on-site time unless you’re prepared for that to get way out of hand.

Keep In Touch

Talking of the bodies you left on the battlefield/your new network of valuable business contacts, you might be surprised to discover just how much you relied on them for your social interaction.  Think of staying in contact as an exercise in networking.

Regardless of whether or not you’re going to maintain a working relationship with your employer, a nice touch when you leave is a farewell email.  This assures everyone that you’re only leaving, not dying, and you’re always happy to advise your replacement. Resist the impulse to put the word “replacement” in quotes.

Record everyone’s contact details and birthdays, anniversaries, or upcoming events.  You can use these dates as an excuse to drop a line and remind people that you’re still available – for whatever reason or purpose.

You, 2.0

Stocking your office with the old-school sundry of supplies is not as necessary as it was just a few years ago.  What you do need is mostly intangible and it’s the best sort of intangible, the free sort. This is assuming you’ve already got the computer and high-speed internet requisite for anyone seriously planning to make a living as an at-home entrepreneur. You need Skype or Google Talk, you need email and you need your standard business software — a word processor and spreadsheet at the minimum. For these last two you can get OpenOffice or just use the software you already have: Google Drive is your free, in-the-cloud storage but they’re also fully functional document and collaboration software.

This is the era of Web 2.0 which means, among other things, applications that run in a browser. The above-mentioned office tools, your email client, calendar, and chat software no longer have any excuse taking up space on your hard-drive. And if you go with an integrated suite like that offered by Google or Microsoft it’ll all magically synchronize with your phone.

The Balancing Act

So now you’re home and you’ve got your virtual office and contacts and, ideally, a couple of lucrative clients. No one’s looking over your shoulder and the only one who can tell you when to work is you. This can be, of course, a recipe for disaster.

The simplest way to stay organized as you transition to working from home is to keep your existing schedule. Don’t set your alarm for later, don’t take three hour lunches. In fact if you can manage it, try to cram as much work into the first part of the day as you can. Sticking to (or exceeding) deadlines is among the very best ways of satisfying your remote clients.  Not sticking to deadlines is probably the absolute best way to lose them altogether.

Having said that, now I’m taking it back. Sure, you need to stay disciplined and organized but try not to lose sight of why you’re making this transition. If you need to be at home to look after the kids then take a couple hours off when they get home from school. Maybe you’re just sick of the commute or the office politics, so take the time you’d spend in the car or in meetings and take a walk around the garden or linger in the bath in the middle of the afternoon.

In short, take the time to appreciate your new lifestyle. Working from home comes with its own challenges and drudgery but if you can stay disciplined and within budget and under deadline, you’re going to love it.

Kathleen Lewis is the founder and owner of, a trusted resource dedicated to providing online jobs from home and.  She understands the trials and tribulations of working from home, and encourages others to act upon their desire to be their own boss. 

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.