Secrets of the Career Game

There is a very loud version of entrepreneurship online right now: quit the job, burn the safety net, go all in, and figure it out later. I get the appeal. I also think that advice can get expensive very quickly, especially when the business has not been validated yet.
Mike Shannon joins me to talk about the much messier, smarter side of starting a business. Mike has built multiple companies, appeared on Shark Tank, worked in AI, and wrote Sweaty Equity, a book about the unglamorous middle of entrepreneurship. His story is not the polished founder myth. It is Shark Tank one day, Chicago Bulls laundry room the next, then years of pivots, investor pressure, customer discovery, and learning how to actually build something that works.
If you are a corporate professional, side hustler, first-time founder, or future entrepreneur wondering whether you should quit your job to start a business, this conversation is your reality check. We talk about why keeping your day job can create runway, why "build the thing, sell the thing" matters more than startup hype, and how to use messy action without blowing up your career stability.
Inside this episode
• Why quitting your job too early can create unnecessary founder pressure
• How Mike Shannon went from Shark Tank with Mark Cuban to the Chicago Bulls laundry room
• Why business validation matters more than investor validation
• The simple startup framework: build the thing, sell the thing
• How customer discovery helps you avoid forcing the wrong idea into the market
• What Sweaty Equity reveals about the messy middle of entrepreneurship
What's one "corporate game" rule you've learned the hard way?
🎯 Take the full Level Up Leadership Course: https://stan.store/thatcareercoach/p/get-started-with-my-play-the-corporate-game-course
About Your Host: That Career Coach, Kendall Berg
Kendall Berg is a career coach and creator, helping ambitious professionals master the unspoken rules of corporate life. Through Secrets of the Career Game, she shares honest conversations and practical tools to help you communicate clearly, lead confidently, and navigate work with strategy — not stress.
☕️ Want personalized career advice? Book a free 15-minute Coffee Chat with me — let's talk strategy, leadership, or your next move.
Book your Coffee Chat → https://calendly.com/thatcareercoach/15-min-follow-up
Want to know more about Kendal Berg, that career coach?
Follow her on Instagram: @thatcareercoach_
Check out her courses on the website: https://thatcareercoach.net/

Watch on YouTube:@thatcareercoach_
About Mike Shannon
Prior to Impruve, Mike co-founded and served as CEO of Packback, which pioneered "instructional AI" for the compliance-heavy Higher Education market with a product suite that scales the teaching impact of PhD college professor clientele. Packback's software earned the trust of the 600 largest institutions and was named one of TIME's Most Innovative Companies in Education. Throughout 12 years, Mike led it from a scrappy startup to $20M in ARR, 100+ employees, and a $50M+ all-cash acquisition by a leading private equity group — earning recognition from Inc. 500, Fast Company, Forbes 30 Under 30, and the Chicago Innovation Awards along the way. But his path wasn't linear. After shaking Mark Cuban's hand on ABC's Shark Tank at a young age, Mike clocked in for his next shift folding towels as a "ball boy" in the Chicago Bulls locker room; a fun tale that culminated in Mike's comedic entrepreneurship memoir, Sweaty Equity: A Ball Boy, A Billionaire, and the Bonkers Startup Tale You've Never Heard, which Mark Cuban described as "a wildly entertaining story!"
Nowadays, Mike enjoys coaching Little League and spending time with his two young kids and wife. He co-hosts Momentum Mode, a podcast featuring private equity-backed CEOs, founders, & investors. He also serves on the board of national entrepreneurship education non-profit Future Founders, where he dedicates yearlong mentorship hours.- www.impruve.com/about

I will be the first to admit I am pretty good at managing my time. But here is the part nobody wants to say out loud: you still cannot do everything.
Every goal, every career move, every family priority, every business idea, and every "quick thing" on your calendar has a tradeoff. Productivity is not about cramming more into your day. It is about deciding what actually deserves your time — and having the structure and support to protect it.
I believe real-time management starts with identity, not your calendar. Who are you at your core? What do you actually believe about your life, your career, and your priorities? Once you know that, you can build a week that reflects your real goals instead of letting your schedule become a dumping ground for everyone else's urgency.
If you are a high achiever trying to balance work, family, career growth, and maybe one peaceful cup of coffee without multitasking through it, this one is for you.
In this episode:
Why real time management starts with identity, not a better calendar

How to clarify your priorities before you plan a single thing

Why ambitious people still cannot do everything — and what to do instead

How to build an ideal weekly calendar that protects what actually matters

Why your productivity has a ceiling without a support system and a village

How to grow your career without burning down the rest of your life

Play the Career Game On Your Terms: https://stan.store/thatcareercoach/p/3-months-of-group-coaching

I know what it feels like to have a "productive" day that somehow leaves you completely disconnected from yourself. You made every meeting, answered every email, handled every priority, and then realized your own health never made it onto the calendar. That is the part of ambition we do not talk about enough.
Dr. Shannon Burge joined me on Secrets of the Career Game to talk about what happens when high-achieving women keep putting health, fitness, and self-care on the back burner until their body forces the conversation. Shannon spent 15 years in Fortune 500 executive leadership, earned her PhD, became an IFBB figure pro athlete, and now helps executives and professionals reclaim their wellness through mindset, nutrition, movement, and community.
This conversation is for the women who are excellent at showing up for everyone else, but keep canceling on themselves. If you are trying to grow your career, lead well, avoid burnout, and still feel like a person outside of your job, this one will hit.
Inside this episode
• Why high-achieving women often put health last
• How to treat your wellness like a real calendar priority
• Why self-care does not mean you are less committed at work
• The four wellness pillars Shannon uses with busy professionals
• How discipline at work can translate into better health habits
• Why fulfillment matters when you are redefining success

Play the Career Game On Your Terms: https://stan.store/thatcareercoach/p/3-months-of-group-coaching
Connect with Dr. Shannon Burge:
Website: www.nodefeat.co
Instagram: @shannon_burge
Nonprofit: www.nodefeatwarrior.com

I used to think balance meant everything in my life would somehow get equal attention. Career, kids, marriage, health, friendships, ambition, personal goals, all of it perfectly arranged like a very unrealistic calendar invite. The truth is, working mom balance does not work that way. Trying to give everything equal priority is usually how burnout starts.
What changed for me was realizing that success requires seasons. Your career can matter deeply without being your number one priority all the time. Your family can matter deeply without requiring you to become a Pinterest mom with endless patience and a homemade snack tray. The real work is choosing your top three priorities, planning around them, and being honest about what support you need to make it actually work.
This episode is for the working mom, working parent, or ambitious professional who is tired of feeling like they are failing at everything because they are trying to do all of it at once. We get into why the balance you were promised does not exist, what to do instead, and why building your village is not a luxury — it is the strategy.
Inside this episode
Why work life balance is not the real goal for working moms

How to choose your top three priorities in this season of life

Why your career cannot always be your number one focus

How planning ahead prevents burnout before it starts

Why working parents need systems, outsourcing, and real community

Why even the CEO of PepsiCo did not bake her own cookies for the bake sale — and what that means for you

Play the Career Game On Your Terms: https://stan.store/thatcareercoach/p/3-months-of-group-coaching

What if success isn't the problem — it's that you've outgrown it? Lauren Kerr introduces the concept of "unbecoming": shedding who you were to step into who you're becoming — without burning out in the process.
Lauren Kerr is a bestselling author and high-performance coach who helps high-achieving women lead with clarity, recover from burnout, and redefine success — without blowing everything up to do it.
If you've hit every goal and still feel like something's off, this is the episode that names what you've been feeling.
What we get into:
→ What "unbecoming" actually means — and why it's not about starting over
→ The silent handbrake keeping ambitious women stuck in a version of success they've outgrown
→ Why the drive that built your career may now be working against you
→ What feminine leadership looks like in practice (empathy isn't a weakness)
→ The "feather or the truck" — why ignoring small intuitive nudges leads to bigger crises
→ Time audits, Parkinson's Law, and how to design a week that actually fits your life
→ Lauren's personal goal this year: just enjoying motherhood (and why that had to be a written goal)


What's one "corporate game" rule you've learned the hard way?
🎯 Take the full Level Up Leadership Course: https://stan.store/thatcareercoach/p/get-started-with-my-play-the-corporate-game-course
About Your Host: That Career Coach, Kendall Berg
Kendall Berg is a career coach and creator, helping ambitious professionals master the unspoken rules of corporate life. Through Secrets of the Career Game, she shares honest conversations and practical tools to help you communicate clearly, lead confidently, and navigate work with strategy — not stress.
☕️ Want personalized career advice? Book a free 15-minute Coffee Chat with me — let's talk strategy, leadership, or your next move.
Book your Coffee Chat → https://calendly.com/thatcareercoach/15-min-follow-up
Want to know more about Kendal Berg, that career coach?
Follow her on Instagram: @thatcareercoach_
Check out her courses on the website: https://thatcareercoach.net/

Watch on YouTube:@thatcareercoach_
 
About Lauren Kerr 
A Best-Selling Author, Mother, and High-Performance Coach for women leading companies and teams who want to create more income, freedom, and fulfilment. With over a decade of experience in Psychology and Coaching, and having built a 7-figure global business reaching the top .05% of her profession, Lauren specialises in helping women optimise and simplify how they think, work, and lead through the lens of feminine leadership.
www.itslaurenkerr.com
www.babesinbusiness.net 
https://www.instagram.com/itslaurenkerr/