Bob Winkelman, CFP® Westward Planning Group, Principal

Bob Winkelman, CFP®
Westward Planning Group, Principal


The sun’s setting in the west spurs us to do our work before the day is done. The west is where we do the work we were meant to do.

The journey that brought me here to do this work began with my Dad. I started working with him, representing a 100 year old insurance company from New England over 30 years ago. We worked mostly with small business owners, helping them plan for growth and eventually the next generation. We worked together for 15 years, over that time the business changed dramatically. We became financial advisors, offering mutual funds and adding retirement planning to the services we provided.

After my dad retired, I continued to work with business owners and I also became a consultant to other financial advisors who needed help with the new more complex insurance products that were developed in the 80’s and 90’s. This gave me a unique vantage point. I could see what consumers wanted and needed and I could see how financial advisors tried to meet those needs. I also saw that only the wealthiest investors had access to comprehensive planning and the emphasis on asset based fees meant that ordinary people who had good jobs but not a lot of assets were all but shut out of the system.

Westward Planning Group was conceived out of a conversation I had with a very successful business owner. He said that he liked his financial advisor but he wasn’t sure if he was getting objective advice. I said, “I think what you need is someone who, for just an hourly fee, will review your planning and investments and give you unbiased advice.” Someone who doesn't sell products or charge a percentage of your assets.” He said, “I would do that in a heartbeat.”

A light bulb went off and I said, “ That’s what I should be doing!”

Financial planning is more than just investment advice, it is about how money affects your relationships, your choices, your freedom.

I created Westward Planning Group to provide comprehensive financial advice for a flat fee to eliminate conflict, serve a more diverse group of people and nurture the whole person through a well thought out plan.

If this sounds like the way your financial future should feel, send me a note here.