Ready to Retire Early?
You’ve saved. You’ve planned. And now you’re ready to take the leap.
You’ve done a great job getting to this point.
But this is the hard part. Before retirement, there are so many questions. So many decisions. And they all matter.
We help you answer questions like…
“Can I retire now, and still be okay 30 years from now?”
We stress-test your timeline, your spending plan, and your portfolio against real-world scenarios so you’re ready for a longer retirement.
“What’s the smartest way to draw income without triggering excessive taxes?”
We create a tax-efficient withdrawal strategy that helps you avoid penalties, reduce lifetime taxes, and make the most of every dollar.
“How will I bridge the healthcare gap until Medicare?”
We work with healthcare experts to explore your options, estimate real costs, and structure your income to make the most of available subsidies.
“What happens if there is a market downturn?”
We work to build you a portfolio and income strategy that balances growth with downside protection.
“How can I avoid wasting money on unnecessary taxes?”
As retirement and tax specialists, we help you time income and conversions wisely, manage tax brackets, and create a strategy that minimizes taxes.
“Should I do Roth conversions now or wait?”
We walk you through the timing, tax implications, and benefits of conversions to help you make sound strategic decisions.
“What happens if I get sick or something major changes?”
We help you build flexibility into your plan so you’re ready for the unexpected.
“There are so many decisions. What if I make the wrong one?”
We guide you through each critical decision, from Roth conversions and drawdown sequencing to healthcare and Social Security. You won’t have to make financial decisions alone.
What we offer early retirees like you
A calm, experienced partner when the stakes are high
The final stretch before retirement is full of critical decisions. We help you understand your options and make the best choices for your situation.
Clarity around your early retirement goals
We pressure-test your plan and model potential scenarios so you can make the leap with confidence.
Expert tax strategy that goes beyond the basics
From Roth conversions to withdrawal sequencing, we help you implement advanced strategies to reduce lifetime taxes.
A healthcare gap strategy that actually works
We work with experts to help you plan for pre-Medicare coverage with a strategy designed to keep your healthcare affordable and sustainable.
A portfolio that supports your income and your timeline
We help you manage market risk, sequence of returns, and growth potential across a longer retirement horizon.
You’ve built the plan; we help you execute it precisely
We understand that you’re not looking to start over. We collaborate with you to fine-tune your approach, not take it apart.
A team always in your corner
As fiduciaries, we’re legally and personally committed to acting in your best interest, offering honest guidance you can trust.
Always available when you need us
Whether it’s a big decision or a quick question, we’re always just a phone call or email away.
Long-term partnership and support
As your life evolves, or the market moves, we’ll make adjustments to help keep you on track.
Case Study
Can we afford a vacation home?
Kathy and George wanted a Florida home in retirement, but also wanted to maintain the financial security they’d worked hard to build. Kenora helped them create a plan that allowed them to do both.
These case studies are provided for illustration only, and do not represent the experience of any specific client, although they may be based on similar client scenarios. Because our services are tailored to your needs, your experience may vary.
You might be wondering...
Is the first meeting free?
Yes. Your initial consultation is complimentary. It’s a chance for us to learn about your goals, walk through your situation, and see if we’re the right fit — no pressure, no obligation.
How difficult will it be to move my accounts over to Kenora?
It’s simpler than most people expect. We handle the transfer process for you, coordinating directly with your current custodian so your investments move securely and without disruption. You’ll have clear guidance on what to expect, and we’ll make sure you always know where things stand.
What does working with you look like after I sign on?
You’ll have direct access to our full team. We review your plan regularly, but we’re also here whenever you have questions — whether it’s a big life decision, a tax-related issue, or just a quick check-in. You’ll never be left wondering where things stand.
Do I have to live nearby to work with you?
No. While many clients are local to Chicagoland, we also work with people outside the area through phone and video meetings. What matters most is fit, not proximity.
Do you specialize in early retirement planning?
Absolutely. Many firms focus only on traditional retirement at 65. We understand the unique challenges of retiring in your 40s or 50s — from bridging the healthcare gap to penalty-free withdrawals, Roth conversion ladders, and managing taxes over a much longer retirement horizon.
How do you help me know if I really have “enough” to retire early?
We build a personalized income and withdrawal strategy that stress-tests your plan against different scenarios. That way, you can see not just if you can retire — but how to stay retired with confidence through market cycles, healthcare costs, and life changes.
What about healthcare before Medicare?
Healthcare is one of the biggest early retirement concerns. We’ll work with healthcare experts to help you evaluate your options — ACA marketplace plans, COBRA, private coverage — and structure your income to keep premiums as manageable as possible until Medicare eligibility.
How do you make taxes part of the strategy?
Because we integrate tax planning directly with investment and retirement decisions, we can help you minimize lifetime taxes. That includes sequencing withdrawals, timing Roth conversions, and managing income so you don’t miss opportunities or pay more than necessary.
Do you work with people who have been DIY planning?
Yes. Many of our early retirement clients have done a lot on their own. We respect the work you’ve put in. Our role is to validate your plan, identify blind spots, and bring the expertise that helps you avoid costly mistakes.
Will I still have control over my investments, or do you take over everything?
Just like a world-class kitchen has only has one chef, and an orchestra only has one conductor, we believe it’s best that you trust us to manage your investments to keep your financial plan on track. But we make sure that you always understand the “why” behind our advice and are comfortable with every decision.
How does your investment approach work for a long retirement?
We build simple, transparent portfolios of individual U.S. stocks designed for long-term growth and clarity. Our focus is on balancing growth with risk management so your money works for 30+ years, without chasing trends or overcomplicating things.
How much does it cost to work with you?
Financial Planning, Investment Management, & Tax Preparation – all on one team
The best way to find out if we’re a good match for your financial planning needs?
Meet the team. See what you think. And don’t worry – there won’t be any pressure, or any pitches. We’re happy to answer whatever financial questions you have!