Teresa Wolande

It’s important to provide honest and timely feedback to your people so they can make adjustments as necessary.


Teresa Wolande is a retired insurance and international risk management professional who is using her expertise to help women through the transition into the fourth quarter of their lives. Through her experience as a working mother, she is leading the establishment of the Women’s Forum in the Naples, Florida area. The goal of this group is to allow women to continue their productivity after their careers have ended and to provide a setting that allows open conversation on how to face changes they experience.

Teresa graduated in 1983 from the University of Iowa with a BS in Economics. After a short time with the Federal Reserve, she accepted a management training position at a large insurance company and eventually worked her way into leading international divisions, working with several well-known corporations. During this time, she found great support in a forum created for herself and others in similar professional roles. It is that experience that helped steer the Women’s Forum she is currently organizing.

Where did the idea for your company come from?

It came from my experience in the Young President’s Organization (YPO) where I was part of a forum. The purpose of that forum was to assist presidents and CEOs of major divisions in companies. We would share challenges, solicit advice, and discuss personal stressors that may have been affecting our professional life.

The forum setting allowed you to have these discussions with others who were one the same professional path as you were. I found that experience incredibly important. When I retired and began to figure out my next steps, I remembered how beneficial this had been. A friend of mine had already started Women’s Forum based on that same structure to help women deal with different stages of their lives.

We had a discussion and agreed it would be a good idea to start soliciting members in Naples, Florida. There is a large community of retirees. The focus there is on the fourth quarter of a woman’s life and how to make that time meaningful for themselves, their families, and their communities.

What does your typical day look like and how do you make it productive?

My typical day starts with exercise. I’ve been that way my entire life. I use the time to fully wake up, get motivated, and plan my day. After that, I immediately reach out and make phone calls with anyone I need to talk to. I still prefer the phone and direct conversation as opposed to email. A lot of my day is filled with those interactions, then following up via email to confirm what was discussed.

My husband and I are involved in philanthropic work, as well. Our primary focus is Catholic Education and we work with several institutions in the Chicagoland area. We are working to enable at-risk youth who qualify for this education but cannot afford to attend.

How do you bring ideas to life?

I am a big believer in vision. If you close your eyes and can see it, you can achieve it. When the idea for the forum first came up, I could immediately see it all. I could see the people who would be interested in joining, I could see how it would affect the community in a positive way. I knew it was going to happen. It’s just a matter of keeping that positive outlook and getting it off the ground.

What’s one trend that excites you?

One trend that excites me is the millennial generation with their great positives. This generation is not into building and acquiring things, they are interested in acquiring experiences. They are looking for new things to do and to learn. They are introducing their children to these experiences also. In the long run, that leads to a much more fulfilling life.

What is one habit of yours that makes you more productive as an entrepreneur?

Every Sunday night, I sit down and plan, in a very detailed way, all that I need to accomplish for that week. I take note of who I need to connect with and what steps I need to take with whatever project I’m working on. It’s a critical habit for me because, at the end of each week, I can look back and make sure I have met all my goals. It helps me stay productive with so much going on.

What advice would you give your younger self?

Don’t be in such a hurry. I think about that a lot now that I’m retired. I was in such a hurry all my life that I never took the time to step back and enjoy what I had accomplished at the time. I was always looking for the next thing.

Tell us something that’s true that almost nobody agrees with you on.

One of the things I became a big believer when I was still working for large companies was making sure that we provided monetary bonuses to everyone in my division. I was sick and tired of working with a consulting firm to improve our work flow processes. We were spending a lot of money for their services.

One day, I asked my supervisory staff what their ideas were for making those improvements. I told them if they could successfully accomplish productivity, they’d get a bonus. At the time, everyone thought I was nuts, but my idea was that those who see the day to day issues were the best equipped to recognize any problems and put a solution into practice. Their suggestions revolutionized our productivity and saved the company a lot of money.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I recommend giving feedback to your employees. I think, especially when you are just starting out and so busy with everything, you tend to forget that step. It’s important to provide honest and timely feedback to your people so they can make adjustments as necessary. It also allows you to give them the acknowledgment they deserve for what they do well and to hear their concerns. A lot of companies have an annual performance review. I made sure.to meet with my team individually at least once a month. They are your best asset as an entrepreneur.

What is one strategy that has helped you grow your business?

To grow a business, you need to be out there talking about it all the time. You never know who may be listening. Don’t underestimate the power of networking. You could be at a social function having a discussion and someone nearby may overhear and express their interest. The opportunity to grow is everywhere if you take the time to recognize it.

What is one failure you had as an entrepreneur, and how did you overcome it?

Early in my career, I decided we needed to do a system upgrade. It wasn’t the right time, it was close to the end of the year, but I forged ahead. I thought the improved efficiency outweighed the risks. Thank goodness, I had a colleague who took me aside about halfway through the implementation and simply stated that there was no shame in pulling back and waiting for a better time. That is what I did. I went to management and owned up to the mistake. I explained how it would be fixed. It’s important to not be afraid to change course if you need to.

What is one business idea that you’re willing to give away to our readers?

I’ve thought about this. If anyone would find a way to put a blow dry salon inside one of the major commuter stations, I think it would be a successful endeavor. As a working woman, I know that I would have taken advantage of such a service given the time it saves and how great it makes you feel. So many women would hop on an earlier train in order to get their hair done before heading into the office. Not my area of expertise – but this would be a home run, believe me. You cannot order a blow dry on Amazon.

What is the best $100 you recently spent? What and why?

The best $100 I’ve recently spent was on a Vitamin C serum. I honestly think every woman should get some. We often forget to take care of ourselves, but this helps with keeping the youthful appearance we want, and I love it.

What is one piece of software or a web service that helps you be productive?

I use a meditation app daily. It helps me to refocus and relieves any tension I may have from the daily grind. It gives me fifteen minutes of relaxation that is so important to staying productive.

What is the one book that you recommend our community should read and why?

I highly recommend everyone read ‘The Whole Brain Child’ by Daniel J Siegel, MD and Tina Payne Bryson Ph.D. It gave me so much insight on how to help my children in raising their children. So much has changed since when I was young and raising my kids. The book details how the brain develops from adolescence into teenage hood. I wish I had that resource when I was still raising mine.

What is your favorite quote?

“There is no try, there is only do”

Key Learnings:

• It’s important to provide honest and timely feedback to your people so they can make adjustments as necessary.
• To grow a business, you need to be out there talking about it all the time.
• The opportunity to grow is everywhere if you take the time to recognize it.