To Job or Not To Job

When should a founder or business owner look for other work?

And we’re back with a new installment of the Brain Trust advice column!

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Sad at work. This guy looks like an early hire at a mid-2010s dropshipping company. He’s going to take those little things out of those boxes and put them into other boxes and mail them to people who don’t know that the things are really from Alibaba. The horror! Jobs can suck, so why do you want one? Photo by Christian Erfurt on Unsplash

Our reader question: “Sarah, you recently shared that you are looking for a job. When do you think a founder should consider going back to work?”

Jobs jobs jobs. Can’t live with them…and that’s the end of that sentence for most entrepreneurial types. The job fantasy is often a short brain twitch that emerges in response to times of stress and overwhelm in your company. Almost every founder and small business owner I know has a very specific fantasy that they play out in their head, smooth as a worry stone.¹ If you desire to bring that fantasy into reality, you might have one of three reasons, some better than others.

1. You Need Money

The primary reason that founders consider going back to work is money. It’s an extension of the employment fantasy: you show up, you do stuff, you get paid. Sounds easy!

But, it’s not necessarily.

Founders who are seeking work because they want money are generally in one of two places:

1. The business/their life needs a cash infusion so they can continue to grow the business

2. The business is failing and they need a new career

If your business is relatively established and you have people you can sell to it may be worth trying to, uh, sell something. I’ve coached many folks over the years who need money but won’t ask their customers to buy something. Finding a job takes time, and is highly unlikely to give you a fast ROI. You are much better off putting together a new offer, dusting off an old one, relaunching something, or even sharing a discount code. If you have customers, they’re going to buy from you faster than you will get hired.

The time thing is a factor here. Despite plenty of chatter to the contrary,² once you’ve gone business owner, you become much harder to hire. Companies are going to be afraid that you’re too use to being in charge and can’t take direction. Your skills are also going to have become more divergent and generalized, and less easily able to fit into the stiff boxes that most roles look for. Even a part-time job can take several weeks or more to go through the hiring process, and then it’ll be a couple more weeks at least until you get a full paycheck.