Should You Be Your Own Boss?

By Kat Gordon

Ditching your corporate job to become your own boss? A high five to that – plus three things to consider before you quit.

15 years ago to the day, I left my big ad agency job and hung out my own shingle. I still recall the giddy feeling of bidding adieu to the traffic, office politics, vacation-request forms – hell, even the unflattering lighting.

Was it worth it? You bet. Was there a learning curve? Um, yes. A serious one.

The beauty of being your own boss – no one will tell you what to do!!!! – has a flipside few consider. No one will tell you what to do! You will have to know what needs to get done and you will have to muster up the motivation to do it.

So before you turn in your badge, ask yourself:

How distractible am I? The imposed work environment and hours of your current job – while insufferable at times – focus your energies on the task at hand. Will you be able to draft a proposal or edit an article – when the siren call of Pinterest and the beeping dishwasher and – oh, look, the mailman just came! – plot against your singular attention? If your honest answer is that you lose focus easily, don’t despair. It needn’t derail your dreams of being a solopreneur. But it might mean you need to consider renting an office space outside of your home (as I’ve done) and imposing other rules like using Freedom software which locks you out of the Internet for hours you decide. Whatever will keep you honest about getting things done, do it.

How many hours do I want to work every week? Hands-down, the hardest part of being your own boss is managing your time. You realize how much your previous boss ran interference for you, doling out projects with some understanding of the hours involved and what else was on your plate. How much can you do? How fast? How much should you charge? The economies of your new arrangement need to work for your bottom-line rather than running you ragged. Remember: the whole point of starting your own business is to take control of your life. So forecast your earnings for the first three months and then keep a detailed log of your hours and billables. You’ll be way off, I guarantee you. But you’ll recalibrate and find ways to work smarter and use your time in more profitable ways.

What can I simply not do? For me it was technology. I’m the kind of nincompoop who wants an IT guy on speed-dial just in case my computer wigs out on me. I have learned the art of Googling for Answers (“how to size YouTube videos in WordPress?”) but I also have learned the art of Jeremy. He’s my IT guy and, at $100/hour, I still consider him a bargain. The mental derailment of an uncooperative printer or questionable backup vanish instantly when I know Jeremy’s on the case. That frees me up to stay focused on what I do best, which is being a Creative Director. Figure out what your most dreaded tasks are – billing, research, trip planning, cold calling – and decide whose help you can enlist to get them done.

Still ready to jump ship? Good! Here’s wishing you smooth waters on your new venture, with you as both captain and crew.

Kat Gordon is the founder of The 3% Conference and founder and creative director of Maternal Instinct, an agency dedicated to marketing to mothers. Prior to launching her own agency, Kat worked as a senior copywriter at Hal Riney & Partners and Andersen Lembke. She has spoken at The 140 Conference, Savor the Success, APNA, Mom 2.0 Summit, and Rock the World. Visit Maternal Instinct and The 3% Conference