6 Retirement Planning Strategies from Business Leaders

To help you plan for a financially secure retirement, we asked six professionals, including CEOs and Managing Partners, to share their most effective strategies. From embracing automatic contributions and investments to prioritizing consistent savings and professional advice, these leaders offer valuable insights into personal financial planning for retirement.

  • Embrace Automatic Contributions and Investments
  • Leverage Health Savings Account Benefits
  • Diversify Across Multiple Asset Classes
  • Invest in Stocks, Bonds, and Real Estate
  • Utilize Self-Directed Solo 401(k) for Entrepreneurs
  • Prioritize Consistent Savings and Professional Advice

Embrace Automatic Contributions and Investments

“Set it and forget it.” For me, this has been the best strategy or mindset to follow for retirement planning. I set up an auto-transfer to fund my IRA/401k automatically every month so that I never forget to do so, and so that I always meet the maximum contribution for my Roth IRA ($541 a month for 12 months equals $6500, which is my annual maximum contribution).

I also set up automatic investments for the day after the automatic transfers. This ensures I’m investing on a regular schedule in a diversified array of investments and not trying to time the market. When you set up an automated system such as this, you don’t have to think about it. You can simply check in once or twice a year to make sure you’re on track to meet your goals.

Meredith LeporeMeredith Lepore
Content Strategist/Editor/Writer, Credello


Leverage Health Savings Account Benefits

One effective retirement-planning strategy I have implemented is taking advantage of a Health Savings Account (HSA). By keeping my deductible health care costs to a minimum and contributing the difference between them and my annual limit to my HSA, I can reap the dual benefits of tax-free contributions combined with tax-free withdrawals when using funds for qualified expenses.

This singular move has helped me save more money while also preparing for any future medical costs during retirement that may otherwise have depleted much of my savings. The flexibility of utilizing this type of savings vehicle means I can achieve both short-term and long-term financial goals without compromising on security.

Julia KellyJulia Kelly
Managing Partner, Rigits


Diversify Across Multiple Asset Classes

Diversification is a key retirement-planning strategy in my financial plan. I own a business, franchises, real estate, invest in the stock market, and maximize my Roth IRA contributions. This diversified approach has significantly contributed to my retirement security.

Diversification involves spreading investments across various asset classes to reduce risk. My business and franchises offer potential high returns but also come with higher risk. Real estate adds stability and potential appreciation, while the stock market offers growth but can be volatile.

Maximizing my Roth IRA contributions is a crucial part of this strategy. It provides tax advantages, allowing my investments to grow tax free. This means I can withdraw earnings in retirement without additional taxes, enhancing my long-term financial security.

Rick ElmoreRick Elmore
CEO, Simply Noted


Invest in Stocks, Bonds, and Real Estate

One of the most effective retirement-planning strategies I’ve implemented in my personal financial plan is diversifying my investments. This strategy has not only spread out my risk but also allowed me to take advantage of various market sectors. By investing in a mix of stocks, bonds, and real estate, I ensure my portfolio is not overly dependent on one type of investment.

This diversification strategy has helped me prepare for a financially secure retirement by creating multiple income streams and protecting against major losses in any single investment area. It’s a long-term approach that requires patience and discipline, but its effectiveness is undeniable.

Michael LazarMichael Lazar
Executive, ReadyCloud


Utilize Self-Directed Solo 401(k) for Entrepreneurs

The Self-Directed Solo 401(k) is a retirement-planning strategy that has been a cornerstone in my financial plan. Given my entrepreneurial role, this plan allows for higher contribution limits and the flexibility to invest in a broader range of assets. Unlike traditional 401(k)s, the Self-Directed Solo 401(k) allows for diversification into alternative investments like real estate, providing both tax advantages and a hedge against market volatility.

Implementing this strategy has been instrumental in fortifying my retirement nest egg while offering the adaptability that entrepreneurs often need. It’s not just about saving; it’s about smart, strategic investing that aligns with my risk tolerance and long-term objectives. I highly recommended this strategy for other business owners or self-employed individuals looking for a robust and flexible retirement-planning solution.

Fahd KhanFahd Khan
Director of Marketing and Technology, JetLevel Aviation


Prioritize Consistent Savings and Professional Advice

I’ve prioritized consistent savings throughout my career. This involves setting aside a portion of my income regularly into retirement accounts. By doing this, I’ve steadily accumulated funds over the years, taking advantage of compound interest. This disciplined approach has been the cornerstone of my retirement plan, ensuring that I have a financial safety net for my post-work years.

Diversification has been crucial in securing my retirement. Instead of putting all my savings into one type of investment, I’ve spread my investments across various asset classes. I’ve allocated a portion to stocks for potential growth, bonds for stability, and real estate to diversify further. This strategy mitigates risks and maintains a balanced, sustainable growth trajectory for my retirement funds.

Seeking professional advice is vital. It helps me fine-tune my retirement plan to align with my specific financial goals and risk tolerance.

Roy LamRoy Lam
CEO and Co-Founder, GeniusHub Digital Marketing


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Greg Grzesiak is an Entrepreneur-In-Residence and Columnist at Grit Daily. As CEO of Grzesiak Growth LLC, Greg dedicates his time to helping CEOs influencers and entrepreneurs make the appearances that will grow their following in their reach globally. Over the years he has built strong partnerships with high profile educators and influencers in Youtube and traditional finance space. Greg is a University of Florida graduate with years of experience in marketing and journalism.

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