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15 Free Retirement Planning Checklists [New for 2025]

Avoid costly retirement mistakes with these handy guides, checklists, and workflows.

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Download and Start Using Checklists For All Aspects of Retirement Including:

Does an annuity fit within my financial plan?​

If I retire early, should I buy health insurance through the health insurance marketplace?

What issues should I consider when reviewing my investments? 

Will I avoid medicare enrollment penalties?

Should I take a pension as a lump sum??

What issues should I consider before I retire? 

Will my social security benefits be reduced?

What issues should I consider regarding my restricted stock units?

What are the most important tax numbers to know for this year?

cash flow in retirement checklist

Retirement is essential - but how do you prepare?

Let's face it: preparing for retirement can be daunting. Making your money last 25 years or more can be incredibly stressful, especially when you've never done it before .

Strong pensions are becoming harder to find at U.S. employers. But, even if you have a pension, the rising costs of healthcare makes it imperative that you understand all of the considerations necessary for a comfortable retirement. 

 

To get you past the oh-so-common feeling of pre-retirement anxiety, we've put together an entire library of checklists we use with clients every day. 

With these retirement planning checklists, you'll get a head start on maintaining financial security in retirement, maximizing social security, and understanding key tax planning insights to help you reduce taxes in retirement.

 

Make preparation for retirement easier! 

  • WHAT IS A FIDUCIARY?
    A fiduciary financial advisor is a financial professional who is legally and ethically obligated to act in the best interest of their clients. As fiduciaries, these advisors must put their clients' interests above their own and disclose any potential conflicts of interest. Fiduciary financial advisors are held to a higher standard of care than non-fiduciary advisors, such as broker-dealers, who are only required to recommend "suitable" investments to their clients. In contrast, fiduciaries must act in their clients' best interest at all times, and must disclose any potential conflicts of interest, such as compensation they receive from recommending certain investments or products. Fiduciary financial advisors may be registered investment advisors (RIAs), who are regulated by the Securities and Exchange Commission (SEC) or state securities authorities, or they may be certified financial planners (CFPs) who have agreed to adhere to a code of ethics and standards set by the Certified Financial Planner Board of Standards.
  • WHAT ARE YOUR FEES?
    At Covenant Wealth Advisors, we believe in transparency when it comes to our fees. We want to ensure that you fully understand our pricing structure and the value we provide to our clients. Before we engage in a relationship, we'll identify the appropriate fee structure based upon your needs and the type of financial advice that you seek. Our goal is to deliver meaningful and valuable advice that far exceeds the fees we charge. We typically charge one of two ways: Wealth management: For wealth management clients, we typically charge an annual blended fee based upon a small percentage of the assets that we manage on your behalf. Contact us for a quote. ​​ Financial planning: For clients who want a financial planning relationship and are comfortable with tax laws and implementing investment recommendations on their own, we typically charge a fixed annual retainer fee, billed quarterly, depending upon your situation. This fee is typically waived for clients who start with wealth management. We never receive commissions and we never receive payments from third parties or product companies, thus reducing conflicts of interest. *Investment Management Fees are payable quarterly, in advance of the quarter, and deducted automatically from the portfolio.
  • WHAT DOES FEE-ONLY MEAN?
    A fee-only financial advisor is a financial professional who only charges clients for the advice and services they provide. These advisors do not earn commissions or any other type of compensation from the sale of financial products, such as investments or insurance. As a result, fee-only advisors are often seen as having fewer conflicts of interest, as they are not incentivized to recommend particular products to clients. Fee-only financial advisors may charge clients in a few different ways, such as a percentage of assets under management, a flat fee for a specific service, or an hourly rate. Regardless of the fee structure, the key characteristic of a fee-only advisor is that they do not receive any compensation from financial products they recommend or sell to their clients. The National Association of Personal Financial Advisors (NAPFA) is the most recognized professional association for fee-only financial planners. NAPFA financial advisors are frequently quoted by the financial media due to their perceived competence and form of compensation, which reduces conflicts of interest.
  • DO YOU GUARANTEE YOUR SERVICES?
    Yes. We understand that establishing a relationship with an advisor you can trust takes time. That's why we provide a service guarantee whereby we will refund 100% of the fees you paid within the first six months if you are unhappy with our services for any reason. As is the case with any financial advisor, we do not guarantee returns or future performance.
  • WHAT IS A REGISTERED INVESTMENT ADVISOR?
    A Registered Investment Advisor (RIA) is a financial professional or firm that provides investment advice and manages assets for clients in exchange for a fee. RIAs are regulated by the Securities and Exchange Commission (SEC) or state securities authorities, and, unlike brokers, must act as fiduciaries. This means they are legally required to act in their clients' best interests.
  • WHAT IS THE DIFFERENCE BETWEEN A CFP AND A FINANCIAL ADVISOR?
    A Certified Financial Planner™ (CFP®) is a professional designation that requires individuals to complete rigorous coursework, pass an exam, and have at least three years of financial planning experience. CFP®s must also adhere to a code of ethics and ongoing continuing education requirements. A financial advisor, on the other hand, is a broader term that refers to anyone who provides financial advice to clients. While some financial advisors may have earned the CFP® designation, not all do, and there are no standardized qualifications or requirements for using the title. In summary, a CFP® is a specific type of financial advisor who has met certain education, experience, and ethical standards, while a financial advisor is a more general term that can encompass a range of professionals with varying levels of expertise and qualifications. Covenant Wealth Advisors has two CFP®s on staff.
  • DO YOU RECEIVE COMMISSIONS OR SELL PRODUCTS?
    We do not sell products or receive any commissions from product companies or third parties. As a fee-only advisor, we earn a fixed percentage fee on the assets that we manage or a fixed fee for developing a financial plan for a client. Clients pay us directly for the services we provide. We believe that working with a fee-only advisor who does not receive commissions better aligns our interests with yours and helps to reduce your total costs because we are seeking products that can do the best job at the lowest cost.
  • HAVE YOUR ADVISOR'S BEEN SUED OR DISCIPLINED FOR ANY REASON?
    No. At Covenant Wealth Advisors, you can trust that all of our advisors have a spotless record in terms of discipline and litigation. For your security and peace-of-mind, we recommend checking the SEC's Investment Adviser Public Disclosure Database for every individual advisor's profile as well as any other adviser or firms with whom you are considering doing business. Your financial future is too important not to take this step. You can find a link to the SEC's Investment Adviser Public Disclosure for each of our advisors below: Mark Fonville Katherine Fonville W. Scott Hurt Broderick Mullins Megan Waters
  • WHO IS YOUR TYPICAL CLIENT?
    Our typical client is someone age 50 plus with $1 million or more of liquid investment assets (excluding real estate). In addition, you are likely a good fit if: You want a personalized plan to help you transition to retirement and not just investment management. You want to know your spouse will be in not just good, but great hands You value having a "certainty of outcome" over simply "beating the market"
  • WHAT ARE YOU QUALIFICATIONS TO PROVIDE FINANCIAL ADVICE?
    At Covenant Wealth Advisors, clients work with a team of advisors with the credentials and experience you deserve. Your team will include a CERTIFIED FINANCIAL PLANNER™ professional, a CPA, and an investment advisor. We work together as a team to provide you trusted, consistent advice and guidance. We're passionate about what we do. We're good at what we do. Learn more about our team's credentials here.
  • DO YOU HAVE AN INVESTMENT MINIMUM?
    Yes. Our clients benefit most from our expertise when managed investments (your combined accounts under management) total more than $1 million dollars. We are dedicated to ensuring their success through tailor-made solutions and services that best meet their goals, needs, and circumstances.
  • DO YOU HOLD MY MONEY OR HAVE ACCESS TO MY ACCOUNTS?
    Our clients’ funds are typically custodied with either Charles Schwab or Fidelity as independent custodians. For many clients, this provides reassurance and a system of checks and balances, as their money is not physically held by the same company who advises on how to invest it. Clients have priority access at any time as well verbal approval authorization required prior to money transfers; written approval must also be granted when transferring funds externally. Our advisors are able to quickly adjust investments if needed, but will always consult our clients on such changes that impact previously discussed financial plans/strategies before executing them.
  • DO YOU WORK WITH CLIENTS REMOTELY OR VIRTUALLY?
    Our advanced suite of technology platforms enable us to provide quality advice and service for clients located far away or unable to meet in person. Video calls, virtual meetings, intuitive planning tools and intelligent account opening processes ensure that our client experience is efficient yet seamless - no matter the distance! Currently (as of 2/14/2023) we have clients located in 22 states.
  • HOW OFTEN WILL I MEET WITH MY COVENANT WEALTH FINANCIAL ADVISOR?
    Establishing a strong and ongoing relationship with our financial advisors is essential for success. We recommend scheduling two to three meetings at the outset—the first being an informational gathering about your finances and family priorities, followed by more focused conversations around specific planning or investing strategies. We build on this foundation by creating a recurrent meeting rhythm that meets each household's individual needs, while feeling confident knowing we are available all year long should any questions or concerns arise over the course of your journey. Typically, we proactively reach out to clients every three months to schedule a financial review/update.
  • WHAT KIND OF REPORTING AND TOOLS DO YOU OFFER TO CLIENTS AND HOW OFTEN?
    At Covenant Wealth Advisors, we strive to provide our clients with access to the highest-quality technological tools and services. We understand that tracking financial progress requires more than just a traditional brokerage statement; this is why we invest in leading performance and reporting platforms like Tamarac. Tamarac offers clear visuals on both high level data as well as detailed metrics of investments through desktop or mobile devices at any time--simplifying how you monitor your finances! Additionally, customized static reports are sent quarterly so that all analysis includes fees for an accurate representation. Our comprehensive investment model also incorporates Money Guide and Holistiplan: a trusted tools used by some of the industry's most esteemed professionals which can help ensure plans stay adaptable over time while weighing potential planning and tax decisions against future scenarios.

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Disclosures: Covenant Wealth Advisors is a fully independent, fee-only wealth management firm and registered investment advisor located in Richmond and Williamsburg, VA. We are a fiduciary. This means we must always put client interests ahead of our own. We are also a fee-only firm. This means we never receive commissions or third party payments and are only compensated by our clients for advice.

 

Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital.The views and opinions expressed in this content as of the date of the posting, are subject to change based on market and other conditions. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax or legal advice. If you would like accounting, tax or legal advice, you should consult with your own accountants, or attorneys regarding your individual circumstances and needs. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place.

© Copyright 2025. Covenant Wealth Advisors, Inc. All rights reserved. Covenant Wealth Advisors is a Registerd Investment Advisor located in Richmond, VA and Williamsburg, VA. View

 

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Disclosures:

Services offered by Covenant Wealth Advisors (CWA), a fee only financial planner and registered investment adviser with offices in Richmond, Va and Williamsburg, Va. Registration of an investment advisor does not imply a certain level of skill or training. Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks. Investments involve risk and there is no guarantee that investments will appreciate. Past performance is not indicative of future results. By entering your info into our forms, you are consenting to receive our email newsletter and/or calls regarding our products and services from CWA. This agreement is not a condition to proceed forward. Case studies presented are purely hypothetical examples only and do not represent actual clients or results. These studies are provided for educational purposes only. Similar, or even positive results, cannot be guaranteed.

 

Awards and Recognition

 

Covenant Wealth Advisors was nominated by Newsweek/Plant-A-Insights Group in November of 2024 as one of America's Top Financial Advisory Firms for 2025. You may access the nomination methodology disclosure here and a list of financial advisory firms selected.

 

CWA was awarded the #1 fastest growing company by RichmondBizSense on October 8th, 2020 based on three year annual revenue growth ending December 31st, 2019. To qualify for the annual RVA 25, companies must be privately-held, headquartered in the Richmond region and able to submit financials for the last three full calendar years. Submissions were vetted by Henrico-based accounting firm Keiter. 

 

Expertise.com voted Covenant Wealth Advisors as one of the best financial advisors in Williamsburg, VA  and best financial advisors in Richmond, VA for 2025 last updated as of this disclosure on February 12th, 2025 based on their proprietary selection process. 

 

CWA was nominated for the Forbes Best-In-State Wealth Advisor 2022 ranking for Virginia on April 7th, 2022. Forbes Best-In-State Wealth Advisor full ranking disclosure. Read more about Forbes ranking and methodology here.

CWA is a member of the Better Business Bureau. We compensate the BBB to be a member and our BBB rating is independently determined by the BBB.

 

CWA did not compensate any of the entities above for the awards or nominations. These award nominations were granted by organizations that are not CWA clients. However, CWA has compensated Newsweek/Plant-A Insights Group for licensing and advertising of the nomination and compensated Expertise.com to advertise on their platform.

 

While we seek to minimize conflicts of interest, no registered investment adviser is conflict free and we advise all interested parties to request a list of potential conflicts of interest prior to engaging in a relationship.

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