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 Episode
- How 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 research
- The pandemic moment that pushed her to leave a full-time director of design role
- The 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 leave
- How 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 profession
- The 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 time
- How 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 working
Episode Highlights:
00:00 - Finding Monday Joy
00:12 - Podcast Premise Intro
00:38 - Meet Martha Malloy
01:27 - Early Career Chapters
05:37 - Bosses Vs Mentors
07:14 - Leading With EQ
10:45 - Reinvention At Work
11:38 - Morning Routine Mastery
16:46 - Pandemic Pivot Consulting
18:59 - Product Discovery Coaching
21:54 - Solopreneur Doubts Wins
27:29 - Embedded Coaching Approach
31:32 - Root Causes, Problems, and Outcomes
32:30 - Industry Agnostic Work
36:04 - Fighting Shiny Objects
37:39 - Parenting Tech Passion
39:08 - Reinvention Mantra
40:14 - AI Meeting Pressure
43:56 - Too Many AI Options
48:42 - Kids Career Reframe
51:56 - Productivity Without Tools
55:25 - Efficiency As A Love Language
56:36 - Future Jobs Unknown
57:32 - Wrap Up And Thanks
Resources Mentioned:
- Designing Your Life — book by Bill Burnett and Dave Evans
- Designing Your Work Life — book by Bill Burnett and Dave Evans
- Willful — Canadian estate planning company; Martha's first freelance client
- Marty Cagan — product management thought leader; Martha attended his "Coaching the Coaches" training in New York
- Product Bets & Jams — Martha's coaching practice; https://www.betsandjams.com/
- BMW Canada — Martha spent nearly five years on this account on the agency side
Martha 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/
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Email: whytotheway@gmail.com
This 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.
