Katie O'Malley, Founder and Principle Coach of Encourage Coaching has grit. She's navigated a variety of spaces from the political realm to real estate to higher education and now, to coaching.
In this episode of the Career Adventurer Podcast, Katie shares insights from 15 years as a career coach and workplace strategist. We talk practical career tools. We talk the highs and lows of her journey. Most importantly, we talk about how she learned to bet on herself.
Through Encourage Coaching, Katie offers leadership and career coaching with a mission to provide accessible coaching services. She talks about building her coaching practice, when you should use a leadership coach versus a career coach, her personal journey of overcoming mental health challenges, and leaving an early mark in politics.
Listen to the full episode. You’re sure to pick up a nugget or three for your own career adventures. At a minimum, you’ll know what to look for if you need a coach.
Core Themes
Katie shares personal experiences and career management tools you might find helpful. Take note of these themes for your own career adventures.
Pick the Right Tool
Do you need a leadership or career coach? It’s kind of like using a Phillips Head screwdriver when you need a flathead. Knowing the difference is key. Picking the right tool could save you time and effort. Lately, I’ve met plenty of people who’ve worked with the wrong type of coaches. They’ve need career selection coaches not leadership advancement coaches.
Katie hit the nail on the head. She clearly captured the difference. Career coaches are best when we need to pick a new path. Leadership coaches help empower you on the current path.
“ Leadership coaching is for folks who love what they're doing, but can't seem to get to that next level or seem to be able to retain and engage their employees. Career coaching is for folks who are looking to make either a pivot, re-enter the workforce for any number of reasons, or get out of a toxic work environment.”
Admit Wrong Moves
There’s probably times when you’ve seriously questioned your path. Your stomach churns. You don’t rest as easily. You want to flee, but you’re conflicted for all sorts of reasons. Maybe you’re conflicted: you dream of a new journey, but the money and prestige is too good to give up. Or, maybe you know you made the wrong move.
When Katie made a leap into the real estate business, she knew it was the wrong move. Similar to many of us, she made the move to make more money. She stayed for a few years, but knew it was the wrong path almost immediately.
“I made that move, and it wasn't even the first couple of days. It was the first day, Paul. It was lunchtime. My former office building at the AIDS Foundation of Chicago was just down the block and I had lunch on my very first day at my new job back with my old colleagues because I'm like, I don't know what I've just done, but this has been the wrong step”
Prioritize Mental Health
Are you prioritizing your mental wellness? In 2021, Olympian Simone Biles withdrew from the Tokyo Olympics Women’s Gymnastics All-Around final to prioritize her mental health. She had the twisties. Her courage and fame put a spotlight on the importance of the mind as well as the body. Biles bounced back, solidifying her claim as an Olympic G.O.A.T. with more medals both in 2021 and 2024.
Katie decided to take a step back from work to prioritize her own mental well being. Beyond Katie, I have friends who’ve taken time off or even quit their jobs due to toxic workplaces. In fact, according to the Surgeon General’s Framework for Workplace Mental Health and Well-Being, 55% of employees think that their employer believes their workplace is more mentally healthy than it actually is. Katie reminded people to know the benefits they have with FMLA.
“In 2012, I ended up taking medical leave from my job for my mental health, which at the time, we were hardly talking about mental health, much less mental health in the workplace. It was very confounding to my colleagues and to HR because they're like looking at me saying, Katie, you're physically okay. And my response would be, I know I look physically okay, but I wake up every morning crying.”
Career Dissonance
Making career choices is tough. Oftentimes we follow in our families footsteps or stay on the path we know because it’s easiest to process. We like to believe that humans desire what’s novel, but according to Derek Thompson we tend to select the familiar.
So how do we make better choices and not just do what’s familiar. Katie uses a decision matrix with her clients. For specific options, they use factors like personal strengths, values and more to create an objective score for further evaluation. It helps clients look at their choices more objectively. In the end, we make better choices.
“There's just…choices. The moment that we can remove and suspend judgment from that, we're actually free to make the choice that we think is in our own best interest. I always say, ‘If you don't like the choice, you can make another one tomorrow. We can realign.’”
Bet on Yourself
On occasion, my wife will say “If it’s to be it must be me.” She learned this phrase from a former manager. His point was that it’s your career and you need to make it happen. You can’t just sit back and wait for opportunities to come along.
This applies regardless of your setting. For Katie, it applied directly to her decision to leave her gig in academia to go all-in with Encourage Coaching. She wasn’t starting from zero. She had built up a nest egg and client base with her coaching side hustle. But, she knew full-time effort could yield more.
“I turned 40 and I said to myself, if I'm not going to go all-in and bet on myself now, I'm not. I'm not sure I ever will. And so January 2022 put in my resignation at Chicago booth…but my goodness, Paul, it is amazing how much you can grow a business when you can spend 40 to 50 hours a week working on it instead of just accepting referrals”
Hear Katie’s Extended Story
Katie is leaving her mark in the coaching world. She is finding her way with grit and practical tools. Like many of us, she doesn’t have it all figured out. Everyday is an opportunity to refine, to improve.
Go beyond the themes. Listen to the full episode. Katie provides more insight and tools that could help you forge the way.
Enjoy the episode! Thanks for you support!
Paul G. Fisher
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