Every generation - no, actually, every individual - has their own ideas about what work is, how much and for how long they want to work, and what retirement will look like for them.
Which is why some days I’ll talk to a current owner who is 60+, never plans to completely stop working, and needs income from the business to fund their retirement while the future owner is in their 30s and sees work as a means to living the life they want, not a calling.
Or an owner who is in hospice and still booking new business while their successor wants to retire.
Or an owner who isn’t ready to sell but is very eager to be out of direct client work and day-to-day operations while revenues can’t currently support new hires.
Or a prospective client who chose the hard work of being an owner to have the freedom to ‘do things how and when I want to do them,’ but sees profits (and the freedom they bring) declining.
The more in touch you are about what work is and what it means to you the more likely you are to
- Define success for you and your business on your terms
- Have a clear idea about if, when, and how you want to retire
- Understand how your plans impact the lives of others - family, employees, successors
- Openly communicate what your plans are
- Engage people dedicated to helping you make your plans a reality
- Take action to make changes that improve how your business works for you
You can start getting more comfortable with the ‘big’ questions related to work, retirement, your life’s purpose, and your legacy by asking yourself questions that shift your thinking from “who am I related to others?” to “who am I at my core?” Try one of these:
1. The "Who Am I?" Challenge
- List 10-15 words or phrases that describe you.
- Remove any descriptors that define you in relation to others.
- Keep words that stand alone.
- Analyze what remains.
- What do these words reveal about you?
- Do they align with how you see yourself when you’re alone?
- If few words remain, what does that say about how you define yourself?
- If your list feels empty, what traits would you like to define you outside of relationships?
- How can you strengthen those aspects of yourself?
2. The Subtraction Method
- Ask: If everything external was taken away—career, relationships, achievements—who would I be?
- For example: Imagine waking up with no memory of your past. What qualities would still be part of you?
3. The “What Would Stay?” Exercise
- List the top 5 ways you usually introduce yourself to new people.
- Imagine you had to introduce yourself without mentioning:
- Your business
- Family or relationships
- Where you live or grew
- What’s left? What parts of you are intrinsic rather than defined by things like your business?
4. The Mirror Test
- Stand in front of a mirror and describe yourself out loud—without using any labels or external roles.
- For example: Instead of “I’m a business owner," say “I love solving problems and helping things grow.”
- Keep refining until you get to deeper truths about your essence rather than your role or title.
5. The “Five Lives” Exercise
- If you could live five completely different lives, what would they be?
- For example: Writer, traveler, scientist, artist, healer.
- What themes appear across these lives?
- What do those themes tell you about who you are in addition to being a business owner?
6. The Inner Compass Test
- Imagine you move to a new place where no one knows you.
- You can’t tell people what you’ve done or achieved. You can only show them who you are through your actions.
- What actions would you take?
Contact me to learn more about how Purpose First Advisors can help you get the most out of your business and plan for ‘what’s next.’
