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So You Want to Keep Your Day Job?

November 25, 2008

As a relatively “green” entrepreneur that are not too many areas in which I feel like I can give meaningful advice, but this is an area where I have a bit of experience so I figured I would share my thoughts.

Lately there has been a lot of talk in the startup world about whether or not entrepreneurs should take the plunge and go full time with their startups in the current economic climate. In fact, there have been some pretty great arguments from some really smart people that support both sides of the coin.

Many would-be entrepreneurs and startup founders, for whatever reason, need to keep their day job… kids, wife that needs “security” etc, etc until they have some level of success. So how do you go about managing your day job AND pursuing your startup dreams? Here are my thoughts:

First of all, the hard truth is you can’t serve two masters master (or three or four…kids/wife etc, right?) so SOMETHING is going to suffer. You need to make sure you have your priorities straight, your expectations in check and your head screwed on straight. Until you can jump in with both feet and all your clothes on with everything including the kitchen sink, things are probably going to progress slower than you want.

If you’re like me (impatient) this is a tough one. But, at the end of the day you have to pay the bills and make sure the wife has her winter wardrobe right?

Once you’ve got that worked out, ask yourself how conducive is your day job to working on your startup on the side? Is it flexible? Can you take an hour in the middle of the day to address issues your startup is facing? Are you willing to change your day job to something that would help your startup rather than hinder it?

Having the right day job can go a long way in determing how successful you will be with juggling your startup and your regular job.

For myself, I found this perfect mix of stability and flexibility in working for another company that is really in startup/bootstrap mode and built on entrepreneurial values. The incredible flexibility offered gives me the ability to deal with client issues as they arise and handle other affairs of my venture without having to worry about issues I might be concerned if I was working in a corporate type environment.

Of course, you most definitely can not allow yourself to work on your startup at the expense of getting your work done for your day job. That’s just unprofessional.

Be prepared for success. What happens when your startup really hits and it’s suddenly taking off faster than you could have ever hoped for. If you’re not prepared, you’ll soon be in over your head and probably ticking people off right and left… managers, wives and kids all included. Have a game plan for success that will allow you to preserve all the relationships and connections you have. If your startup tanks 6 months after you finally quit your day job, you better not have burned any bridges at your previous employer!

Expect failure. Depressing or realistic? If you’re not putting 100% in, are you going to be surprised if things don’t work out? Don’t beat yourself up, this is the tradeoff you’re making here. Obviously, you’re slowly/steadily working towards success, but at some point you’re going to have to make a real (ie, 100%) commitment here or things will probably never rocket off the ground.

In the end, keeping your day job while working on your startup is a numbers game, where the forumla for success has these huge untangible variables. It all comes down to that gut feeling that only you will have about your specific situation. If everyone involved is on the same page with expecations aligned, you should be ok.

Written by Bradley Joyce · Filed Under Blog, Startups 

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