Should You Bootstrap While Employed?

Monday, October 8, 2007 at 12:00am by Site Administrator

Shawn Hessinger of BoostrapMe blog had an article last month about how you can bootstrap a business while you’re employed. This article is actually Shawn’s reflection of a similar article written by Penelope Trunk at Brazen Careerist.

Penelope emphasizes something very important by making it number 1 (whether she meant to or not): Don’t tell your co-workers.

And let me re-emphasize that: Don’t tell your co-workers. Do I need to repeat that? Don’t tell your co-workers. Even if you’re putting in extra hours at work, out of your own time, to balance your guilt, and even if your side business is losing money, those the least ambitious of all will make your life hell.

While those ambitious like you will praise you, it’s not worth discovering the other type of workmate to tell anyone at all. Jealous people will assume everything wrong in any action or activity you take. And they’ll spread bull about what you’re doing because it’s easier for them than trying something on their own. It’s harsh, but it’s the truth. Commiserate with like-minded types outside of work, not at work.

In a similar vein, most companies have rules against using their resources for anything not related to your job. And believe it or not, that includes email use, even if you use your free Hotmail, Yahoo, or GMail. At any rate, they can see every email you send and receive anyway, so best you get email/ mobile web access on your personal cell phone.

When I was still contracting offline, and even before when I was employed and bootstrapping on the side, I used my own pagers and cell phones for my business. When mobile web access came along, I jumped on it early out of necessity. I’ve had far too many encounters with the jealous type of workmate. Don’t find yourself in that position.

Still, this all means that you can still bootstrap your startup while you’re employed, but that you should be very cautious about anything to do with it. It’s also tough to assess objectively whether your “bootstrap time” is interfering with your work. But keep in mind that even in states where there are labor laws protecting you, there are ways to get rid of you, to discredit you, or simply make you quit.

My feeling is that you should weigh out these consequences for yourself before jumping into your startup during work hours. What do you think? Have you bootstrapped a business while you were still employed? Did you encounter these problems? How did you cope?

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Filed under: Entrepreneurship


  1. I think I would go a bit farther and not tell anyone who doesn’t need to know – until you are ready for everyone to know. Including your employer. Even children have a propensity for picking up on things that you wouldn’t imagine and then asking pointed questions at the worst possible moment.

    Comment by David LaFerney — October 8, 2007 @ 2:45 pm

  2. Good point, David. Not having kids I didn’t think of that. Even telling all your relatives is a bad idea b/c of some of them may think they’re helping you by telling you all the ways you can go wrong.

    Comment by Raj Dash — October 8, 2007 @ 3:18 pm

  3. And what if it’s too late? What if you’ve already spilled the beans? Just cease and desist?

    Comment by Angela — October 11, 2007 @ 3:51 pm

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