Love Your Mondays: Martha Malloy on Reinvention

Martha Malloy built a successful career in advertising, got promoted fast, worked on marquee accounts — and then quietly fell out of love with it. What came next wasn't a straight pivot; it was a side quest into UX research, a freelance experiment during the pandemic, a training session in New York that made her realize an entirely new profession existed, and eventually a coaching practice she built from scratch with a self-imposed one-year deadline.The throughline across all of it is a question she keeps coming back to: do you love your Mondays?In This EpisodeHow Martha went from studying car design in England to automotive advertising at BMW Canada — moving from coordinator to account director in four years — before realizing advertising wasn't personally sustainable long term and pivoting entirely into tech and UX researchThe pandemic moment that pushed her to leave a full-time director of design roleThe two books — Designing Your Life and Designing Your Work Life — that helped her plan her off-ramp without burning bridges, and the specific exercises she did to decide whether to redesign her role or leaveHow she discovered product discovery coaching at a "Coaching the Coaches" training in New York with Marty Cagan — 50 coaches from around the world — and realized for the first time that it was a legitimate full-time professionThe business coach advice that shaped her first year as a solopreneur: time-box your commitment, give it your heart and soul, and avoid diluting your energy by interviewing for full-time roles at the same timeHow she structures her embedded coaching engagements — from light-touch workshops to joining teams two to four days a week — and why the moment companies choose the "large" option was her clearest signal the business was workingEpisode Highlights:00:00 - Finding Monday Joy00:12 - Podcast Premise Intro00:38 - Meet Martha Malloy01:27 - Early Career Chapters05:37 - Bosses Vs Mentors07:14 - Leading With EQ10:45 - Reinvention At Work11:38 - Morning Routine Mastery16:46 - Pandemic Pivot Consulting18:59 - Product Discovery Coaching21:54 - Solopreneur Doubts Wins27:29 - Embedded Coaching Approach31:32 - Root Causes, Problems, and Outcomes32:30 - Industry Agnostic Work36:04 - Fighting Shiny Objects37:39 - Parenting Tech Passion39:08 - Reinvention Mantra40:14 - AI Meeting Pressure43:56 - Too Many AI Options48:42 - Kids Career Reframe51:56 - Productivity Without Tools55:25 - Efficiency As A Love Language56:36 - Future Jobs Unknown57:32 - Wrap Up And ThanksResources Mentioned:Designing Your Life — book by Bill Burnett and Dave EvansDesigning Your Work Life — book by Bill Burnett and Dave EvansWillful — Canadian estate planning company; Martha's first freelance clientMarty Cagan — product management thought leader; Martha attended his "Coaching the Coaches" training in New YorkProduct Bets & Jams — Martha's coaching practice; https://www.betsandjams.com/BMW Canada — Martha spent nearly five years on this account on the agency sideMartha Malloy is a product coach, startup advisor, and angel investor with 20+ years of experience helping technology teams — from early-stage startups to Fortune 500s — build products people actually want. As founder of Product Bets & Jams, she helps founders and product leaders replace gut-feel decisions with evidence-based practices that stick. She's worked across product, design, research, and marketing, and is an active mentor and investor in women-led companies.Connect with Martha Malloy: https://www.linkedin.com/in/martha-claire-malloy/Connect with Us!http://www.whytotheway.comEmail: [email protected] - Why To The WayYouTube - Why To The WayLinkedIn - Why To The WayLinkedIn - Sarah JeanneaultLinkedIn - Twisted Spur MediaThis show is produced by Twisted Spur Media Ltd.Disclaimer: The views, information, or opinions expressed by guests during Why To The Way Podcast are solely those of the individuals involved and do not necessarily represent those of Sarah Jeanneault, Twisted Spur Media Ltd. and/or her affiliates. Sarah Jeanneault, Why To The Way Podcast, and Twisted Spur Media Ltd. are not responsible for and do not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.