Planning to Retire Early?
You don’t want to work any longer than you have to.
You’ve got a life plan. And early retirement is a big part of it.
But you might still need some help answering questions like these…
“How much is enough to retire early?”
We help you find your number, test your assumptions, and track your progress with a strategy built around your goals.
“Am I saving in the right places or creating a future tax problem?”
We help you balance pre-tax, Roth, and brokerage contributions now so you have more flexibility and fewer regrets later.
“How do I plan for early retirement when healthcare is such a wildcard?”
We’ll work with experts to help you project real costs, explore coverage options, and understand how your income affects what you’ll pay.
“Am I investing the right way for my timeline and goals?”
We help you make sure your portfolio reflects your risk tolerance, withdrawal horizon, and long-term independence plan.
“What’s the best way to turn savings into income when the time comes?”
We help you build toward a strategy now that will make drawdowns simple, tax-smart, and sustainable later.
“Can I support my kids and/or parents and still retire early?”
We guide you through timing, generosity, and boundaries, so you don’t lose your own momentum in the process.
“Should I scale back, take a sabbatical, shift careers, or wait?”
We help you model potential situations so you can make an educated decision.
“Am I doing everything I should, or am I missing something big?”
We’ll review your plan to help you catch gaps, refine your strategy, and move forward with confidence.
What we offer aspiring early retirees like you
A plan built for financial independence before age 65
We help you align your savings, investments, and tax strategy with your early retirement timeline.
Tax-smart savings strategy
Where you save matters just as much as how much. We help you build the right mix of accounts so you have options later, not regrets.
Early retirement clarity
You’ve built a plan, but you need to know it will work. We pressure-test your strategy and model potential scenarios so you can confidently stay on track.
Healthcare planning to bridge the gap
Early retirement requires serious health insurance planning. We work with experts to help you estimate costs and avoid surprises.
A partner for complex decisions
We help you think through tax implications, account strategy, and early exit plans so you can make informed decisions.
Advice without the sales pitch
As fee-only fiduciaries, we’re committed to acting in your best interest with advice that’s clear, objective, and never commission-driven.
Clarity and control
We help you align your plan so your investments, taxes, and retirement strategy work together effectively.
A flexible plan that moves with you
We know your goals will evolve. Whether you accelerate your timeline or decide to shift course, we help you adjust along the way.
Always available when you need us
We’re always just a phone call or email away, for decisions and questions big or small.
Case Study
A smarter path to early retirement
Sarah and John wanted to retire in their early 50s, but weren’t sure if they were on the right path. Kenora helped them create a more tax-efficient strategy for early retirement.
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.
When is the best time to start working with you?
Many of our clients come to us 5–15 years before they want to retire. This is the best time to optimize your plan — while you’re still earning and saving. We’ll help you structure your accounts, taxes, and strategy so you can move toward early retirement with confidence.
I already have a spreadsheet and a plan. What more can you add?
A lot of our clients were DIY planners. We don’t replace what you’ve built, we refine it. We stress-test your assumptions, identify blind spots (especially around taxes and healthcare), and bring expertise you can’t always get from blogs or calculators. Think of us as a second set of expert eyes to make your plan stronger.
How do you help me know if I really have “enough” to retire early?
We’ll model your unique lifestyle goals against different retirement ages and spending levels. Together, we’ll create a clear roadmap that shows what’s possible now — and what adjustments could accelerate your timeline.
Do you handle tax planning while I’m still working?
Yes. Tax strategy is one of the biggest levers for aspiring early retirees. We help you balance contributions across pre-tax, Roth, and brokerage accounts, manage taxable income, and position your savings so you’ll have flexibility later when you start drawing down.
What about healthcare if I retire before 65?
We’ll work with experts to plan for the healthcare “bridge years” before Medicare. That includes modeling ACA subsidy eligibility, estimating costs, and making sure your income plan supports affordable coverage when the time comes.
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!