Let’s Talk Retirement with Roger Whitney

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In this week’s episode of The Law Practice Doctor, Sam Gaylord interviews Roger Whitney, who is a certified financial planner, investment management consultant, private wealth advisor, and an accredited investment fiduciary. Roger is known as the Retirement Answer Man. During this episode, Sam and Roger discuss setting financial goals and keeping records, mastermind and accountability groups, the ‘little conversations,’ budgeting, and solutions.

Main Questions Asked:

  • Talk about setting good financial goals.
  • What are some of the systems and structures you’ve put in place to get balance?
  • What things do you want to make sure clients are doing when it comes to their financial records?
  • What are some of the problems you see when meeting with clients?
  • Tell us what you mean when you say ‘little conversations.’
  • What should we think about with regards to budgeting?
  • What solutions do you suggest to clients?
  • Tell us about what it means to be the Retirement Answer Man.


Key Lessons Learned:


Setting Financial Goals

  • When you’re a solopreneur, the lines between business and personal life are blurred.
  • A business needs to serve you as much as you serve it.
  • There are ways of structuring the business so it can run without you.


Keeping Financial Records

  • What is your overhead, and how are you tracking that consistently?
  • What is your income, and what things can do you do to manage the income and control the kind of growth you have?


Mastermind & Accountability Groups

  • Start a mastermind group in your area, or virtually, and thoughtfully seek out two likeminded people with similar motivations, goals, and values.
  • This is an opportunity to have weekly video chats or calls as peers with complete confidence and transparency on what each person is struggling with and what is working.
  • Masterminds help you find the blind spots in business.
  • Accountability groups have a weekly meeting where each person revisits tasks they promised to be done during the week.


Common Problems

  • People in general don’t want to deal with their finances in a thoughtful way.
  • It’s not that people don’t have good intentions for the discussion; it’s that the conversation gets put off.
  • Roger essentially provides the framework for conversations about the right things.
  • Most people don’t have a clear concept of what their net worth is.
  • Net worth is the sum of all the assets and liabilities on one page. This is a representation of all the decisions they’ve made with money through their lives.


The Little Conversations

  • Little conversations mean not having ‘big conversations,’ which is when things are out of hand and need to be addressed.
  • Rather than trying to ‘figure it all out,’ the key is to have a process to have thoughtful conversations, so you can make lots of little adjustments and manage uncertainty rather than removing it.
  • It’s the forced engagements that facilitate the littler conversations that deal with the little inklings rather than huge problems.



  • The core goal of budgeting is to control your overhead and to capture free cash flow.
  • Roger sets a spending target each month.
  • The income will go into a separate account from the checking account.
  •  Once a month, the spending target money will be moved over to the spending account.
  • As long as he remains close to the spending target, it doesn’t matter what category it goes under.
  • The key is capturing the excess earnings and allowing that to accumulate.
  • It’s important to have systems in place so money doesn’t get co-mingled.
  • Most people have their income go into the checking account, and it all gets spent.
  • When money arrives in the income account, it’s best to separate the money that will go to estimated taxes.



  • Set your 1, 3, and 5-year priorities as a family, business, or individual.
  • Priorities have the ability to change over time, whereas a goal is finite.
  • Figure out what you are trying to accomplish and make sure your cash flow is in alignment with your priorities.
  • Allocate the net worth statement to align with those 1, 3, 5-year priorities.
  • Use checklists to ensure the little conversations happen.
  • When people think about personal finance, they think too much about investments.
  • Investing is part of personal finance but isn’t the engine that drives everything.


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Links to Resources Mentioned


Roger Whitney 

Retirement Answer Man Podcast


Click To Tweet


The little conversations are crucial when looking at retirement. Find out why w/ @roger_whitney @gaylordpoppllc http://www.gaylordpopp.com.com


Get the best monthly budgeting tips with the Retirement Answer Man @roger_whitney @gaylordpoppllc http://www.gaylordpopp.com.com










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