Trailhead Thoughts
“Be patient with yourself. Self-growth is tender; it’s holy ground. There’s no greater investment.”
- Stephen Covey
Trail Map - Learn. Think. Act. ™
Ready to Invest in Yourself?
Every time you consider a course, coach, or book, you’re making an investment decision. But how do you really know if it’s worth it?
📚Learn
An investment isn’t just about money. It’s also your time, energy, and attention. Resources that both have value, and are limited.
Ask yourself:
What exactly am I investing in?
Why does it matter to me or my goals?
How will the investment work? What’s needed, What’s the plan?
At what cost? (time, money, effort.)
Keep in mind, you can only optimize for two of the three - time, money, quality. Choose your trade-offs wisely.
🤔Think
Use this 2×2 matrix to clarify your decision:
Can the skill be improved?
Is it needed to win?
If the answer is yes to both, that’s your green light to invest.
Process Outcome Matrix
Then reflect:
Where am I now? (current skill level.)
Where do I want to be? (desired outcome.)
What’s the best path? (coach, course, DIY?)
💪 Act
List 3 skills you’re considering improving.
Rate yourself 1 - 5 on each.
Pick ONE to invest in this quarter.
Decide how - coach, course, book, video?
Take the first step this week.
Growth doesn’t come from wishing. It comes from choosing and acting.
Beyond the Trailhead
Stop Accidentally Investing in Yourself
Most people say they care about growth and then end up investing in themselves kinda by accident.
A book here. A podcast there. A random course bookmarked, but never finished. With hope and good intentions sprinkled generously on top.
Let’s stop doing that.
If you’re serious about being driven to greatness, not just staying busy, you have to be intentional about where your time, energy, and money go. Growth doesn’t happen through good intentions. It happens by design.
Every real investment decision asks the same questions:
What am I actually investing in?
Why does this matter?
How will this work?
What am I willing to trade? Time, money or quality?
You can’t have all three. Something always gives. The leaders who move faster simply decide what they’re willing to trade instead of pretending that they won’t have to.
If you don’t choose where to invest in yourself, your calendar, inbox, algorithms and your boss will happily choose for you.
What You Can Do This Week:
Pick one skill that would change your year if it improved. Decision-making. Time management. Communication. Problem-solving. Or something else. But, just one.
Rate yourself honestly (1-5). Not to add guilt or judgment, but to gain clarity. Growth starts with uncomfortable truth.
Choose your investment lane.
Want speed? Get a coach.
Want low cost? Read, watch, test.
Want community? Join one intentionally.
Set a 30-day expectation. Not I’ll be better. But, I’ll practice this skill this way for 30 days and see if it works.
That’s how momentum starts. Not with a massive overhaul, but with a decision you honor.
If this made you laugh, cringe or nod a little too hard, you’re not alone. Forward this to a friend or colleague who’s ready to stop drifting and start investing with intention. Growth gets easier when we stop pretending that we’ll figure it out later.
Reach for more.
Be driven by greatness.
Stop letting hope be your investment strategy.
Voices from the Trail
Meet Mike – founder of Find My Catalyst
This is a “throwback” episodes to the early days of the podcasts.
Training - Is it an expense or an investment.
How do you decide where to invest?
Listen to this episode on Spotify
Hitting the Trail
Are you in charge of planning a company offsite or leadership retreat? Bring in a speaker who won’t only inspire, but will equip and spark action within your team. Mike helps teams turn ideas into execution through clarity, communication, and actionable frameworks.
Whether you want to reset strategy or build momentum, Mike’s sessions are designed to spark alignment and drive results.
Click here for more information.
Announcements
If you’re planning your 2026 strategy, team development, or event calendar, now’s the time to talk.
We work with organizations that want more than hype, hacks, or overcomplicated frameworks.
Here’s how we can support your leadership and team growth in 2026:
Strategic Whiteboard Sessions
For teams that are moving fast and need to realign, reset, and move forward with clarity and shared priorities.
In-House Team Meetings and Facilitation
We help leadership teams navigate change, rebuild trust, and define what “better” looks like
Speaking
Conferences, off-sites, client events, internal development sessions, and podcasts.
1:1 Coaching for High Performers
For leaders and high-performers who are doing well but know they’re ready for something more.
If you want 2026 to be the year that you or your team moves from reacting to leading and performing on purpose, let’s talk now, not later.
Click here to start the conversation.
coachsimmons.com/contact
That’s it for this week.
Keep putting one intentional step in front of the other - the view gets better and better as you climb.
We’d love if you would share this with someone who is ready to build their sprints for the new year.
The Find My Catalyst Team