High achievers are often very good at hitting goals.
Good grades. Important titles. Respected internships. Numerous awards. The recognition is prevalent.
Somewhere between chasing the next milestone and preparing for the future, it is easy to loose sight of what is truly important.
While the flashy titles and awards feel good in the moment, true success is fulfilling and meaningful.
Jason challenges his listeners to rethink success not as something we earn, but as something we build intentionally over time. His insights offer a powerful framework for leaders who want more than a successful résumé.
The contents below are designed to work like a guided worksheet. Take some time to intentionally build meaning into your success. Grab a notebook or open your notes app and dive in!
Step 1: Question the Definition You’ve Inherited
Societal achievements set the traditional views of success. You have probably never truly taken the time to picture success in your own life. It often sounds like a prestigious job title, a high salary, constant productivity and external recognition
Jason challenges this traditional view of success.
Reflection Questions
Take some time getting honest about these questions.
Who or what has shaped your current definition of success?
Which parts of that definition genuinely excite you and which feel like pressure?
If you lost your job title, GPA or leadership role tomorrow, what would still matter?
Step 2: Identify What You Truly Can’t Live Without
Jason encourages leaders to move past what feels urgent and focus on what is essential. Not what society says you need for a successful life but focus on what you actually value.
Check in with your non‑negotiables
Make a short list under each category:
Relationships: Who are the people you want to still be close to in 10, 20 or 40 years?
Meaning & Purpose: When do you feel most useful? Most aligned? Most like yourself?
Well‑Being: What habits help you show up as your best self physically, mentally and emotionally?
Now ask:
Am I actively investing in these things or just assuming they will always be there?
Step 3: Separate Status from Success
Status is visible. Success is personal. You can have status without fulfillment, and fulfillment without status.
Jason shared stories of leaders who “made it” on paper but paid a high personal cost: strained relationships, burnout and regret. His takeaway wasn’t to avoid ambition but to measure ambition across all aspects of life.
Reflection Questions
Where do you feel pressure to appear successful?
In which areas of your life do you feel genuinely proud but rarely talk about?
If your life were summarized in a retirement slideshow, what moments would you want included?
Step 4: Shift from Performance Goals to Identity Goals
High achievers love performance goals. Get the internship. Earn the title. Land the job.
Jason challenges you to dive deeper.
Instead of asking 'What do I want to achieve? 'ask: 'Who do I want to become?
Complete these statements:
I want to be the kind of person who __________.
I value being someone who __________.
People trust me because I __________.
Once identity is clear, behaviors follow.
Step 5: Redefine Success in Your Own Words
Now comes the most important part. Using everything you’ve reflected on, write your own definition of success. Not one that sounds impressive but one that feels true.
Success, to me, means…
Leave space. This definition will evolve as you navigate life.
A Final Challenge
You don’t have to abandon ambition to redefine success.
But you do have to decide whether your goals are helping you build the life you want or just keeping you busy.
Leadership isn’t about what you accumulate. It’s about who you become.
Learn more
Jason Wetzler joins The Cultivating Leaders Podcast for a conversation about redefining success, building identity and prioritizing purpose. Jason shares why real leadership is about becoming the kind of person others trust and follow.