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Will a Good Employee Be a Good Owner?

The first thing I’d ask you is: Do you know what you want to do? Knowing yourself is an important prerequisite to starting a business



I’ve spent the last two years at a job that I really don’t like, but I haven’t left yet because I’m not sure what to do next. My first job (while I was in kollel) was helping fundraise for a local organization. That turned into a full-time job, where I was eventually earning 90K. I’ve been recruited to a number of new ventures since then in construction-related fields. My current position is operations manager.

Every time I join a new business, I’m the one who builds it up, makes it profitable, and am the brains behind the success. Because of that, part of me thinks I should go out and start my own business. What stops me though (besides that I don’t know where I’d get the money to get started) is that I’ve gone through a number of bouts of depression over the years. There are some days and weeks where I’m completely “off.” The rest of the time, I’m the most productive guy on the team. I also don’t know if I’d be good at it — just because I’m a good employee, does that mean I’ll make a good owner?

An employee (for now)


This is a Great question.

I think at least 80% of the population walks around wondering if they should start their own business (or maybe it’s just my clients?). It sounds like you’ve been pondering this question for a while, and there are good reasons in both directions that must be confusing you to no end!

There are huge differences between being a successful employee and being a successful business owner. First, the boring details: your financial reality. Unless you have a solid investor, a spouse whose income is enough to depend on, or simply enjoy living on the edge, experts say to first put away money to cover at least 6–12 months of your expenses.

Next, do you have a solid business plan? By “solid,” I don’t mean a fancy booklet with impressively confusing graphs, but the real story: Have you done your research? Is there is real market demand? Do you know how you plan on capturing that market?

If you’ve worked in the industry, you may have the benefit of having an existing network of people in the field, which would be a huge advantage to getting started. If not, that’s something to start working on well before you ever place your first ad.

Typically, I recommend starting a business on the side, while you keep your day job. Obviously, that won’t always work, whether you’re thinking of starting a similar business to your employer, or simply don’t have the time to juggle a job and a business. When possible, though, it’s the safest way to get started.

Personally, I moonlighted as a career coach for over a year before I quit my day job and took the leap to full-time, in the interim gaining a steady client base and experience. Many business founders started their businesses off as side hustles — including Steve Jobs of Apple, Andrew Mason of Groupon, and Craig Newmark of Craigslist fame.

To answer your specific question about deciding whether to look for a new job or to start a business, the first thing I’d ask you is: Do you know what you want to do? Knowing yourself is an important prerequisite to starting a business, and if you aren’t yet very clear on what your skills are and what you enjoy doing most, I’d be very hesitant to advise you to start out on your own.

Once you’ve nailed down your unique strengths and what you’d enjoy doing, I’d advise you to figure out what kind of business you’d like to have — down to the details — and then get a job working in exactly that kind of enterprise. Then when you would ultimately go out on your own, you’d have significantly reduced the risk factor, since you’d have the exact experience needed in that field.

You shared that

you struggle with depression. I’m not a qualified mental health professional, but I would strongly suggest you work with one, who would help you understand, manage, and make decisions based on your condition. The more “fit” we are in all areas, the better chance we have for success, certainly before making a big decision like starting a new business. The fact that you’re recognizing this issue as a valid concern is important; while depression doesn’t discriminate between business owners and employees, it’s important to factor in the level of responsibility you have to others when you have your own employees. You may decide that the additional responsibility would not be a good idea for you, or you may conclude that working at a job that is a poor fit is a factor contributing to your depression in the first place!

It’s hard to stay at a job when you know that you’re “the brains behind the success,” as you stated. Thoughts of I’m the one doing all the heavy lifting, while my boss enjoys the profits, are frustrating. Funny thing is, ask any business owner if they think they have it better off, and they’ll likely start enumerating the stress, responsibilities, and headaches that they feel their employees don’t begin to understand. But they’ve chosen to own a business, and there’s a reason for that.

Keep nurturing that dream of yours to become an entrepreneur, but take the time to understand yourself, formulate a clear business plan, and learn how to maintain a healthy emotional state, so that you’ll never have to look back at your old job with regret.

I’m rooting for you!


Shaina Keren is a career consultant who helps people discover and create careers that fit their best talents, interests, and life goals. She also advises businesses on hiring and keeping “the right people in the right seat,” in a win-win approach to growing businesses and careers.



Would I make a good business owner?

Do I have enough money to live for 1–2 years?

Do I have experience and a strong network in this field?

Do I have the grit to keep going, even after repeated failures?

Do I have long-range vision?

Have I done market research to make sure this idea is sound?


(Originally featured in Mishpacha, Issue 843)

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