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How would you weigh a corporate career vs starting your own business?

corporate career vs entrepreneurshipI have an opportunity to partner with a very capable person I've known for a long time. Upon further contemplation I have to admit that I haven't really given the notion fair consideration, but merely reacted with INR. That is Initial Negative Reaction, based mostly on the fear of making such a big change and not the opportunity itself or why it might appeal to me.

How would you go about weighing a corporate career vs small business owner start-up decision? Part of me still doesn't want to consider it, just because it involves thinking about some current unhappiness I have, which I try to ignore as much as possible. I also tend to regret the things I haven't done more than the things I have.

I digress. As background, I have no dependents, a little money in the bank and no debt. Also, I don't have to invest, but would have to work with virtually no pay for at least six months.


Robert Greenway
Title: CIO
Company: Private
(CIO, Private) |

Here are a few of the many questions to consider;

How hard would it be to find a comparable position next year to your current work while unemployed should this not work out?

How badly will you regret not taking the chance?

How long could you afford to go without real income?

Is it leaving the current position or going to the new opportunity that really appeals to you? Maybe you just need a change and not necessarily this opportunity.

Do you think leaving for the start-up is mostly about leaving the old job, as in you're due for a change?

What do you judge to be the new ventures true chances for success, given the failure rate of start-ups?

These are the kinds of things I'd be thinking about.

Topic Expert
Simon Westbrook
Title: CFO
Company: Aargo Inc.
( CFO, Aargo Inc.) |

The corporate world is a great place to start. Someone else is paying you to learn about products, markets, finance, building a network of contacts, providing a life opportunity outside of you day job, and maybe even allowing you a chance to accumulate a little savings. But if you want the fun, challenge, and upside opportunity, then working for yourself is something you have to try. I would warn though, that six months living expenses may not be enough for a start up opportunity to turn into a paying proposition!

Cindy Kraft
Title: CFO Coach
Company: Executive Essentials
(CFO Coach, Executive Essentials) |

Having been burned in the "partner" fire before, I personally can say that once "money comes in the door," it is a sure-fire way to ruin what you thought was a great relationship / friendship. Something about money brings out the worst in people sometimes, so if you are going to do this ... get a lawyer and nail out the terms - ALL THE TERMS - before you do anything else.

While many people don't view it this way, in today's economy we really are all self-employed ... even while working for others. Why? At the senior level, you are only as good as your last balance sheet and happy investors, shareholders, Board, and amicable CEO. When things go astray, it is Mr. Finance who often finds his head on the chopping block. When you are in the corporate environment though, you have only so much flexibility to drive that train given the constraints of those to whom you report.

There is a great book - a few years old but still a great read - called "We Are All Self-Employed" and it addresses the similarities between being employed and being self-employed. At least, it is true if you choose to sit in the driver's seat of your career!

I listened to a teaching long, long ago about the difference between western and eastern entrepreneurial mindsets. In the west, we create a business plan, talk to people, refine the plan, talk to more people, make sure ever "I" is dotted and "T" is crossed, and generally find one more risk / challenge / obstacle preventing perfection before launch. In the east, an entrepreneur gets an idea, takes it to the street, comes home, makes a few changes based on feedback, and launches. Sometimes "we" can be the biggest impediment to an effective launch and a successful / profitable business.

Being self-employed is one of the greatest things I've ever done. Sure there have been times when it has felt like one long roller coaster ride, but I would not trade the roller coaster for a corporate position ever. And it's now been 19 years.

I agree with Simon, you should probably plan on 9-12 months ... because that's just the way it works AND it's still a volatile economy. That way, when the cash rolls in quicker, you're surprised and delighted rather than frustrated and anxious!

All the best, M!

Joseph Kershenbaum
Title: EVP, Operations
Company: Salute Homecare LLC
LinkedIn Profile
(EVP, Operations, Salute Homecare LLC) |

After practicing law with a major American firm for 9 years, I walked away from the corporate world. This has included continued partnership offers, general counsel opportunities with public and private companies and the opportunity to become an investment banker. Having made the decision 15 years ago that you are considering now, and built businesses in three different industries since then, I have a few suggestions:

1. Your choice of a partner is the most important decision you will make. A partnership is like a marriage. Knowing someone a long time doesn't mean they will be an appropriate business partner. I have had close friends with successful careers want to form businesses with me, but for various reasons, I know it wouldn't work, but would only destroy our friendship. What is most important is trust and honesty of your partner.

2. Building on 1 above, you must both have strong work ethics. One partner will just get frustrated if he or she is carrying another's load.

3. Building on 1 above, you should have complementary abilities. Two people with the same abilities will have similar blind spots, which increases the risk for the business.

4. Give careful weight to your own motivations. In other words, "Know thyself." Given my experience and connections, I could have chosen the route to a senior position in the corporate world for my whole career, but I wanted to control my own destiny, not just be a cog in the machine. That was more important to me than the money. I I thought that even if I ended up poor, I'd be happier. I did not want to get to the end of my life and say, "What if?"

I've built two successful service companies with co-founders (one had an IPO, one closed post-2008 due to the financial crunch). I'm working on a third that is still pre-revenue. I've had incredibly frustrating experiences where I've lost sleep, but am generally very happy. In hindsight, given my personality and abilities, this was a good choice for me. That said, I wish I'd considered the points I mentioned above more carefully when I started on my journey. Good luck!

Jack Judd
Title: Retired
Company: Retired
(Retired, Retired) |

I think you have been provided some excellent advice. I have one thing to add to your decision making matrix. Make an evaluation on how easy it would be to recreate in the future what you have today for a job. If you feel another job similar to what you have today would be easy or reasonable to attain if you venture goes wrong, it can make it easier to jump.

Good luck.

Anonymous User
Title: CFO
Company: Local Government Agency
(CFO, Local Government Agency) |

You're talking partnership not going into business for yourself. The first is very much like a marriage. It is the absolute worst way to structure a business.

But, that's not to say it hasn't successfully been done. But when it fails, it tends to fail dramatically.


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