Private coaching to help you make sense of what’s changing, solve what’s getting in the way, and build a plan for the next phase—so your days feel clear, steady, and worth waking up to.
30+ years teaching, training, and coaching life transitions
Whether you’re 6 months into retirement or 6 years in, it can still feel harder than you expected. Identity shifts. Relationships shift. Your energy and needs shift—and if what used to work doesn’t anymore, even good days can feel oddly empty.
Together, we’ll get clear on what’s getting in the way and what matters now, fix what’s pulling you off track, and build a plan that fits your real life—so retirement feels steady, meaningful, calm, and yours again.
You’ve already done hard things. You’ve built a life. But retirement can still bring questions you can’t solve with effort alone—because the whole system changed. That’s where I come in. I help you get clear on what’s happening, pinpoint what’s throwing you off, and solve the real-life issues that keep this phase from feeling good.
Coaching isn’t generic advice. Think of me as a thinking partner—someone who helps you sort the noise, ask the right questions, and see what you can’t see from inside your own head. We don’t copy-and-paste someone else’s idea of a “good retirement.” We craft bespoke solutions that match your values, your relationships, your energy, and what you actually want your days to look like.
I’m Rob—an ICF-credentialed coach (PCC) with decades of experience guiding people through major life transitions. My approach is structured, practical, and built for people who want real progress, not vague talk.
If you’re ready, we’ll build a retirement that feels steady, meaningful, and yours.
“This year has had a lot of change for me as you will know. It has been such a privilege to know that I had the additional support from someone experienced to help me gain clarity when things seem overwhelming.”
Scotland
90-Day Retirement Clarity Guarantee so you can commit with confidence which means you feel safe, certain, and excited about what comes next.
Personalized Coaching so you can build a retirement around your values and blind spots which means you feel grounded and like yourself again.
Practical, step-by-step strategies so you can turn ideas into weekly actions resulting in steady progress and real forward motion.
Book a no-obligation conversation to explore your retirement goals, current challenges and whether coaching or a programs is the right fit for you.
We’ll build a tailored plan together—timeline, focus areas, and session structure—so you can start with a clear roadmap that feels aligned, realistic, and worth the investment.
We’ll turn insight into action so you can move from uncertainty to confident direction, purpose, and momentum.
A free 2-minute assessment that helps you identify where you’re thriving and where you may need extra support.
Take it today!
Tailored 1:1 support focused on your specific retirement blind spots, values, and goals—so your plan fits your life, not a generic checklist.
Research-backed tools to map strengths, purpose, vision, and life balance—so you understand what you want this chapter to stand for and how to build it.
Integrates positive psychology, storytelling, emotional intelligence, neuroscience, and more—so you’re not just “staying busy,” you’re building real well-being and meaning.
Decades of teaching, training, and coaching across major life stages—so you’re guided by someone who understands how identity and purpose shift in transitions.
If you don’t gain clearer direction within 90 days, you continue free until you do—so you can move forward with confidence.
Retirement coaching focuses on the parts money can’t solve: purpose, identity, daily structure, and relationships. We’ll get clear on what you want this chapter to stand for, then build a practical plan to live it. It can also help you navigate other issues as they arise.
A financial advisor helps you answer, “Can I afford to retire?” I help you answer, “What am I retiring to—and how do I make it feel fulfilling?” This is the non-financial plan that turns “financially ready” into “life-ready.”
Because big transitions create blind spots—even for capable people. Coaching isn’t a crutch. It’s leverage: a structured way to get clear faster, make better choices, and avoid drifting into a retirement that looks fine on paper but feels off in real life. Working with Rob, you’ll also gain access to decades of knowledge, experience, and a variety of specialized tools and assessments.
Not at all. In many ways, it’s perfect timing. You now have real data: what feels good, what feels empty, and what you miss. We use that to redesign your days with clarity and momentum.
A common rhythm is one online session per week (typically 30–60 minutes), plus any time you need between sessions to complete activities that move you forward. The goal is to help you make steady progress without it taking over your life.
While a wide range of coaching services are available to meet individual needs, packages range from 1 to 6 months in length and from a $500 to $2500CAD investment. Discounts may also be available for clients who qualify. Book a free discovery call to discuss your needs and goals and we can design a package right for you and your budget.
It helps to think in terms of investment, not price. The “price” is what you pay once. The investment is what you get back—week after week—because you’re building a retirement that actually works in real life. You’re not buying advice. You’re investing in a structured process that tackles the hardest, most overlooked parts of retirement: identity, purpose, daily structure, and relationships—so you don’t end up financially prepared but personally adrift. Coaching is a self-investment that protects the quality of the years you worked hard to earn.
Another way to think about it is like this … if your roof is leaking on your house, you can try to fix it yourself, or pay an experienced/recommended professional and enjoy better results and overall experience.
That’s exactly why the 90-Day Retirement Clarity Guarantee exists. If you don’t gain clearer direction within 90 days, you continue free until you do—so you can move forward with confidence.
No. While that is the main focus of On Course Coaching, I have coached youth and young adults for almost 20 years (and continue to do so) through my sister company, Youth Coach Global. If you’re curious if I’d work with you, book a free discovery call and we can determine if we’d be a good fit.
On Course Coaching
172 Bradley Ave.
Binbrook ON Canada
L0R 1C0
+1 (905) 515-9822
info@oncoursecoaching.com
© 2026 Rob Stringer
All Rights Reserved
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