Carol Olsen Weathers Storms to Fly Solo

Currently running a successful software training business, Carol Olsen was looking for something different after she completed her MBA at Northwestern. Having worked for companies ranging from 20 to almost 2,000 employees, she fell in love with wearing all the hats at a small company. Carol shares with WE Source how she turned “something awful” into a successful career and navigated a potentially career-ending cancer diagnosis.

Headshot of Carol Olsen smiling at the camera. She is white with chin-length brown hair, and brown eyes.
What made you decide to make the leap to going out on your own? Have you always wanted to run your own business?

After my MBA, I wanted to go back to a smaller company. When I say small, I mean 25-30 people. A former colleague worked at a small consulting firm and they hired me to run a training division for them. It was like running your own biz with a safety net. It was a great experience, but I was laid off in 2001 when they sold the company.

My plan was to freelance until I found a job at another corporation but I found I wasn’t looking for another job. I was busy enough and after a year I realized I had to start my own business or get a job. And I had no interest in going to work for anyone else. It’s really awful to get laid off but I might never have done this otherwise, even though I think this is the best thing for me.

What keeps you motivated?

I like the flexibility of being my own boss. There are days, even weeks, when I’m not motivated or burnt out because I travel and it does wear on you. But it always come back to the fact that I like what I do and I don’t want to work for anyone else.

Did you need funding?

No, in large part due to networking. What I teach is very expensive. I was fortunate to have good relationships and some of those people went out on their own as well and I was able to make a deal to provide training at a lower rate in exchange for the software I need. That money savings was huge. Without that I absolutely would have needed funding. More than 90% of my business has been due to word of mouth and it all goes back to the people I bartered with and who they referred me to.

Do you have a business plan?

No. I would tell someone that they should, though. I never did a formal mission statement. But I did go to business school so in the back of mind I know the specific service I offer. I may branch out in how I deliver, but I do Cognos® training. I get random requests to train on other software but I’ve chosen not to. I know my specialty and my goals, but I think I would have been more focused and organized if I had a business plan.

Who do you ask for advice?

I belong to a women’s group through my grad school that I would go to for advice and I have consultants and friends who understand my business that I go to sometimes. I think it’s a flaw for me. I’m not really good at asking for help.

"You have to pick yourself up and dust yourself off. For every project you don’t get there will be two others you do get. I’ve managed to pick myself up more than once and I’m still in business." Carol Olsen

What’s been the single biggest struggle since opening?

In 2006 I was diagnosed with breast cancer. I’m fortunate it was early stage, but my first reaction was “I’m going to lose my business.” Did I lose projects? Yes, but I didn’t lose customers. I didn’t tell my clients about my diagnosis, I just said that I wouldn’t be able to travel for 5 months for health reasons, and most of them were able to work around that. If I’d have to have chemo, I probably would have lost my business because if I couldn’t deliver for 6-8 months people would find someone else. There weren’t any resources and it was very frustrating. It was because of my strong client relationships and a relatively short recovery time that I am still in business.

What are advantages or disadvantages to being a woman in business?

I think there are starting to be more companies that are interested in diversifying. I’ve had some customers require me to prove I'm a woman-owned business. I can’t say for certain that it’s gotten me jobs but it has helped me be in the running for jobs I might not have been in the running for otherwise. But sometimes you’re not taken as seriously as a woman.

How do you deal with failure?

You have to pick yourself up and dust yourself off. For every project you don’t get there will be two others you do get. I’ve managed to pick myself up more than once and I’m still in business.

What will you be celebrating in a year?

I’m looking at expanding to new things. Maybe new ways of client delivery or new software, but I am looking to do more and different things.

Where do you see yourself in five years?

I hope I’m traveling more for fun and less for business, and focusing on enjoying life. But still thriving in business. I definitely know it’s not going to be the same—I just haven’t refined my vision yet.


Thank you.

Our success story Entrepreneur

Carol Olsen


Carol Olsen & Associates, Inc.

Carol Olsen, MBA, has been providing in-person and remote training solutions of the highly sophisticated Cognos® business intelligence software for almost 20 years through her eponymous company.

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All views and opinions expressed by the entrepreneurs interviewed are their own and do not represent those of Bank of the West WE Source, Bank of the West, or its affiliates. Carol Olsen & Associates, Inc. is not affiliated with Cognos® and is not an official Cognos partner. Cognos is a registered trademark.