My Biggest Obstacle in Starting a Business

I’ve been asked to write about the biggest business obstacle I faced when I started a business. I’ve thought about it. It took some time. I developed some lists. But, after consideration, here’s what it came down to:

My one biggest obstacle was needing the money.

My family depended on my income. We had several small children, I had the fancy MBA degree and the only income. We had business school debts, a mortgage to pay, and running expenses. All of that, against the background of quitting a good job to do my own thing instead, with all of the related risks, was pretty hard to overcome. I might cite confidence, but it could also have been a bad decision with a good outcome, due to plain good luck.

A lot of people who need the money keep the real job, and don’t set out to do their own thing, or build a new thing.

Furthermore, as I look back on it, I don’t want to be advising anybody else to do as I did. If you do, then at least make sure you plan really well. Reduce the uncertainty as much as possible.

I was driving with my youngest daughter over the weekend. She’s 21, soon to be starting her fourth year of college, and thinking about her future. That might be the ideal time of life to start a business, if it weren’t for the experience and know-how factor, because there are few ties and dependencies. Ironic: more age increases the chance of success, but also increases the weight of alternative options.


  • Joanna Van Vleck says:

    Yes! I love this thought–at the beginning seems like a wonderful time to start a new venture. That is what I did. There was no one else to support, not payments to make, and guess what–people are willing to help because they know you are young! They know you have courage. I say, go for it!

  • John Caddell says:

    Tim, that was my situation as well. When I was ready to go out on my own, I resisted the impulse as long as I had a job that paid well. Eventually I was forced into it–in short, that good paying job went away.

    What a blessing that has turned out to be!

    But throughout, a key part of the business plan was/is being able to pay the mortgage each month.

    regards, John

Leave a Reply

Your email address will not be published. Required fields are marked *