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This week's conversation was inspired by something we keep hearing from our community: people who feel capped — financially and creatively — in their current jobs and are wondering what to do about it. Do you add something on the side to generate more cash flow? Or is it time for a full-on career change?
What we talked about:
The difference between a "side hustle" and a career change — and why I'm personally trying to retire the word "hustle." I prefer thinking of it as a lateral option to generate more cash.
Why spending less isn't the only answer. We talk a lot about budgeting as a society, but what about creating cash injections? Most of us have skills we're seriously undervaluing.
Chris painted our entire house for under $3,000 — saving us $15,000 in contractor quotes. That's a real-world example of a monetizable skill most people don't even think about.
When a career change makes more sense — you've hit your income ceiling, you're dissatisfied, or (as many people are experiencing right now) you're doing the same or more work for less pay.
The golden handcuffs conversation — we talked honestly about what it feels like to be 15 years away from a pension in a job you hate. That's a hard truth.
Chris's career change from construction to financial services — he shares what it really took, and why having a mentor who followed up made all the difference.
What to ask yourself before you leap:
Can you handle inconsistent income? Do you have a buffer (ideally 6 months of expenses)?
Are you willing to give up some evenings and weekends while you're building?
Is your job the problem — or your income level?
What does success feel like (not just look like) for you?
Multiple profit streams — my mentor Jack told me early on: never have just one. Even if you're in a niche, build more than one way to generate revenue.
Lifestyle shifts when you change careers — especially if you go from something physical (like construction) to something sedentary. We talked standing desks, walking pads, and our 2-3 daily walks.
Our own retirement vision — we plan around 60-65 and think in terms of best case and minimum case scenarios. Luxury for us means slow mornings, walks, and a warm mug — not a Four Seasons lifestyle.
Let's dive in!
Thank you for joining us today. If you could rate, review & subscribe, it would mean the world to me! While you're at it, take a screenshot and tag me @jennpike to share on Instagram – I'll re-share that baby out to the community & once a month I'll be doing a draw from those re-shares and send the winner something special!
Click here to listen:
Apple Podcasts – CLICK HERESpotify – CLICK HERE
This episode is sponsored by:
withinUs | Use the code JENNPIKE20 at withinus.ca for a limited time to save 20% off your first order and 20% off your first subscription order
St. Francis | Go to stfrancisherbfarm.com and save 15% off your all your orders with code JENNPIKE15
Eversio Wellness | Go to eversiowellness.com/discount/jennpike15 and save 15% off every order with code JENNPIKE15 /// not available for "subscribe & save" option
Free Resources:
Free Perimenopause Support Guide | jennpike.com/perimenopausesupport
Free Blood Work Guide | jennpike.com/bloodworkguide
The Simplicity Sessions Podcast | jennpike.com/podcast
Get 20% on thewalkingpad.com using code "JENNPIKE20"
Metabolic Guide | jennpike.com/metabolic-guide
Get discounts at happybumco.com using code "JENNPIKE"
*code doesn't apply with Black Friday sale*
Programs:
Ignite: Your 8-Week Body Transformation Program | https://jennpike.com/ignite
The Peri & Menopause Project - Join the Waitlist | jennpike.com/theperimenopauseproject
Synced Virtual Fitness Studio | jennpike.com/synced
Services: Work With Jenn | https://jennpike.com/work-with-jenn/
Functional Testing | jennpike.com/testing-packages
Business Mentorship | The Audacious Woman Mentorship: jennpike.com/theaudaciouswoman
Connect with Chris:
Instagram | @chrisborsellino
Finance Discovery Session | Book Here
Connect with Jenn:
Instagram | @jennpike
Facebook | @thesimplicityproject
YouTube | Simplicity TV
Website | The Simplicity Project Inc.
Have a question? Send it over to [email protected] and I'll do my best to share helpful insights, thoughts and advice.
By Jenn Pike4.7
115115 ratings
This week's conversation was inspired by something we keep hearing from our community: people who feel capped — financially and creatively — in their current jobs and are wondering what to do about it. Do you add something on the side to generate more cash flow? Or is it time for a full-on career change?
What we talked about:
The difference between a "side hustle" and a career change — and why I'm personally trying to retire the word "hustle." I prefer thinking of it as a lateral option to generate more cash.
Why spending less isn't the only answer. We talk a lot about budgeting as a society, but what about creating cash injections? Most of us have skills we're seriously undervaluing.
Chris painted our entire house for under $3,000 — saving us $15,000 in contractor quotes. That's a real-world example of a monetizable skill most people don't even think about.
When a career change makes more sense — you've hit your income ceiling, you're dissatisfied, or (as many people are experiencing right now) you're doing the same or more work for less pay.
The golden handcuffs conversation — we talked honestly about what it feels like to be 15 years away from a pension in a job you hate. That's a hard truth.
Chris's career change from construction to financial services — he shares what it really took, and why having a mentor who followed up made all the difference.
What to ask yourself before you leap:
Can you handle inconsistent income? Do you have a buffer (ideally 6 months of expenses)?
Are you willing to give up some evenings and weekends while you're building?
Is your job the problem — or your income level?
What does success feel like (not just look like) for you?
Multiple profit streams — my mentor Jack told me early on: never have just one. Even if you're in a niche, build more than one way to generate revenue.
Lifestyle shifts when you change careers — especially if you go from something physical (like construction) to something sedentary. We talked standing desks, walking pads, and our 2-3 daily walks.
Our own retirement vision — we plan around 60-65 and think in terms of best case and minimum case scenarios. Luxury for us means slow mornings, walks, and a warm mug — not a Four Seasons lifestyle.
Let's dive in!
Thank you for joining us today. If you could rate, review & subscribe, it would mean the world to me! While you're at it, take a screenshot and tag me @jennpike to share on Instagram – I'll re-share that baby out to the community & once a month I'll be doing a draw from those re-shares and send the winner something special!
Click here to listen:
Apple Podcasts – CLICK HERESpotify – CLICK HERE
This episode is sponsored by:
withinUs | Use the code JENNPIKE20 at withinus.ca for a limited time to save 20% off your first order and 20% off your first subscription order
St. Francis | Go to stfrancisherbfarm.com and save 15% off your all your orders with code JENNPIKE15
Eversio Wellness | Go to eversiowellness.com/discount/jennpike15 and save 15% off every order with code JENNPIKE15 /// not available for "subscribe & save" option
Free Resources:
Free Perimenopause Support Guide | jennpike.com/perimenopausesupport
Free Blood Work Guide | jennpike.com/bloodworkguide
The Simplicity Sessions Podcast | jennpike.com/podcast
Get 20% on thewalkingpad.com using code "JENNPIKE20"
Metabolic Guide | jennpike.com/metabolic-guide
Get discounts at happybumco.com using code "JENNPIKE"
*code doesn't apply with Black Friday sale*
Programs:
Ignite: Your 8-Week Body Transformation Program | https://jennpike.com/ignite
The Peri & Menopause Project - Join the Waitlist | jennpike.com/theperimenopauseproject
Synced Virtual Fitness Studio | jennpike.com/synced
Services: Work With Jenn | https://jennpike.com/work-with-jenn/
Functional Testing | jennpike.com/testing-packages
Business Mentorship | The Audacious Woman Mentorship: jennpike.com/theaudaciouswoman
Connect with Chris:
Instagram | @chrisborsellino
Finance Discovery Session | Book Here
Connect with Jenn:
Instagram | @jennpike
Facebook | @thesimplicityproject
YouTube | Simplicity TV
Website | The Simplicity Project Inc.
Have a question? Send it over to [email protected] and I'll do my best to share helpful insights, thoughts and advice.

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