I guess I have achieved the age where people think I’m old enough that I must actually know some stuff because I keep getting asked for advice. It’s nice to think that people believe I have something useful to say about careers, life, and where to get the best shoes.
It’s also kind of weird to think that I am perceived as having answers to these big life questions. Flattering, but weird. Don’t get me wrong, I love telling people what I think they should do. I am just amazed when they think I’m right. I mean, I am a parent so I know what the opposite looks like.
I am writing this blog post from a plane, flying to Las Vegas for the HLTH Conference and there is a guy in the seat next to me who is wearing a t-shirt that says, “Bourbon Goes In, Wisdom Comes Out.” Maybe that explains my state of sage-ness.
But what made me want to write this blog, aside from the idea that more bourbon might move my chess pieces even further forward, is a wonderful chat I had Friday with a woman I didn’t previously know until she reached out through CSweetener. I was particularly psyched to chat with her given that HLTH’s Foundation affiliate acquired CSweetener from me some years ago and has continued to invest in its ability to thrive and provide mentorship to rising women in healthcare. It’s basically like match.com for connecting experienced mentors, male and female, together with rising female executives and similarly situated people. I thought it was a good idea when I started it, but now I know for sure, as it has stood the test of time, how much people yearn for guidance, input, camaraderie and ideas to spur their imagination.
Since the woman who reached out to me through CSweetener was pretty far down the line of achievement in her career, I was curious to know what she thought I could offer. She told me she wanted to hear about my career path and how I got to where I am. I probed a little tiny bit harder – what really was she after? Since I have quite a few decades to cover on the “how I got here” front and we had only 30 minutes, where should I focus for her? Certainly she did not want me to start all the way back in the Disco era? Very sorry about those legwarmers, by the way.
She told me she wanted to hear about two things: 1) What was the plan I implemented that got me to my current career place (I am paraphrasing, but about right); and 2) How I got to a place of high resilience and confidence. I made myself some notes about what I said, and I am sharing them here for those who wouldn’t rather reminisce about the leg warmers.
My Grand Plan for Building My or Any Career

First of all, plan-shplan. Anyone who tells you they had a plain and executed on it step by step like building a Lego Italian Riviera Set is lying to you.
Fighting words, perhaps but totally true. I have said many times that there is no such thing as a straight line towards a goal in one’s career (probably not anywhere). What matters is what you make of what life puts in front of you (good and bad), who you meet along the way, and that you do what you can to build your environment in such a way that more opportunity and luck comes at you.
For me, this meant that I was lucky enough to have an amazing couple of first jobs where I learned a ton from people who felt it worth investing in me and my growth – this was particularly true at my first healthcare startup job. I also had some epically bad experiences, including working for a full-on white collar criminal (in tech…not healthcare).
I have said to whomever will listen that it’s all about the people and I will shout that to the rooftops til my dying day. For all of you early in your career, don’t chase money, don’t chase influence, chase good people who give a damn that you are riding in their awesome wake and not drowned by it. If you find yourself among smart, driven kind people who offer you their hand, stop talking and just take it. A strong foundation is essential to a great career and the only way to build that is through aligning yourself with people who really want to be your Sensei, not your overlord, and who just know a lot of stuff and how to think about new stuff well. Not rocket science. But in the end, it actually turns out to be 100% rocket science because it starts the rocket every time. If you’re not learning things when you start out, get out. Find a place that wants to nurture you and is excited about that for themselves too.
While people who care about you and whom you care about invest in you, you take the time to invest in your network. I’d say the single best thing I did after having the luck of a great foundation was this. I have made an effort to mix and mingle and meet new people every week of my career life in some way. I have a job that helps make this real, but I also make a point of doing it even when I feel tired and lazy (often), cranky and antisocial (oftener), or otherwise like I’d rather be alone with my dog and a pint of ice cream. I fight that urge tooth and nail and get out among people, reach out to new ones, spend time on a permanent listening tour in order to acquire a network of awesome people. It is an even better collection than my shoes, and if you know me, that’s saying something.
One of the best things about mentoring through CSweetener is that I always learn something too. Network development, when done right, is a two-way street to everywhere. No one I know who has their dream job got it just from some ad on LinkedIn. They got it by planting, cultivating, feeding, and harvesting their network. And from giving to others while they were waiting for the garden to feed them. Embrace the chaos. Go to all the things. Stand in the COVID soup (fully vaccinated of course). And also, have some side gigs (job approved, of course) where you learn even more stuff and meet more people. It comes back in ways and multiples that you will never expect.

In fact, this is my last answer to the first question. In the immortal words of The New Radicals “Can’t forget, you always get what you give.” It’s so true.
Women who push other women down because they think there can only be one Queen Bee are just flat out wrong. I run with a whole posse of Queen Bees, and we love and support each other every step of the way. Just because we are competitive or driven in general doesn’t mean we need to beat each other down or at all. Everyone gets a turn at the front of the hive and, as it turns out, there is a lot of room up there on the honeycomb frontage road. And when it’s someone else’s turn to stand in front, applaud like crazy and give them the genuine support they deserve.
I always try to help people with information, contacts, support, whatever as much as I reasonably can without losing sight of what I have to do or trading on people’s or my own relationships in ways that would compromise them. I don’t keep tabs of who I helped or what anyone owes me. I just know that my posse is going to answer my call when I need them because I had the courtesy to do the same. That’s how you get ahead. You pull each other up and don’t charge interest. The world is not driving towards this goal right now and it makes me feel in ways that make me incredulous and nauseous.
On Confidence and Resilience
As for how I got to a steady state of self-confidence and resilience, well, hang on for a minute while I stop laughing uncontrollably.
I do not believe that anyone who is honest with themselves ever really achieves these in steady state. I know that I can go from the depths of the Grand Canyon to the height of the International Space Station in about 11 seconds on any given day. Twice. And stop for snacks in both directions. This applies to self-confidence, feeling resilient and all of the other great stuff people aspire to have but, once again, are totally lying if they say they have completely mastered them at all times.
It’s not that I don’t think I know my stuff, but I also know that I don’t know it all and that I must always have my learning mode switched on. I can feel confident in the moment and then later have an acute attack of imposter syndrome, just like everybody else, and want to do that thing where Homer Simpson slinks into a shrub. Sometimes I feel like I am a so-called expert and want to pontificate. And then 15 seconds later I find out I’m not so damn smart as I thought I was and I need to get my humble hat back on.
Confidence needs to be defined more effectively, in my opinion. It should be less about the state of being entirely sure of yourself and more about the ebb and flow of knowing when you aren’t the smartest guy in the room but are reasonably adjacent enough to know when you need to listen rather than talk. No one ever achieves self-confidence to a point that they 100% shake imposter syndrome or insecurity. They just get much better at hiding it. And they get much better at managing it by recognizing when it’s just a syndrome and not just actual stupidity. Learn this skill, keep learning with an open mind, and you will ultimately come to find that confidence is an ever-fluid state. When you get comfortable with being somewhat uncomfortable sometimes, you will be a winner and more confident. But don’t get cocky about it.
As for resilience, I think it’s pretty similar, to be honest. Resilience is best seen in the rear-view mirror. You only know you have been truly resilient when you can look back and recall some very low moments and recognize you are doing well in the current one. And then, someone comes along and slaps you back to the ground again., rightly or wrongly, fair or unfair. You can declare yourself resilient when you somehow get to a point where you can remember you dug out of the hole successfully before. That’s my definition of resilience—having the internal memory that your world has gone to hell before and you managed to climb out, so you have a shot at doing it again. I’m not sure it gets any easier, it just gets more familiar, and the muscle memory is stronger.
if you don’t feel that you are getting a lot more confident or resilient as you progress through life, what can you do about it? I think you can actually do a couple of important things. Constantly take stock of what really matters to YOU and spend a lot less time worrying about what matters to other people. And then stick to your guns. It feels weird at first to put yourself first, particularly if you are one of those people who doesn’t naturally do that (I see you moms). I don’t mean that you shouldn’t care about what matters to the important people in your life, but if you’re doing life right, what matters to them should be highly synergistic with what matters to you anyway. What I mean is that you should not let the nay-sayers and criticizers and those whose morals and ethics you do not admire get in the way of your good decisions. And to do that you have to make some people uncomfortable sometimes. And that is just ok. Life is hard. Wear a helmet.
I recently saw a trailer for a new Julia Roberts movie, After the Hunt, where she sidles up to a young woman and with quiet intensity says to her, “Not everything is designed to make you feel comfortable.” It just gave me chills because it is so damn true. If you can own that statement and live your truth and realize that when you do you feel better and are often right, you will have more blips on the confidence oscilloscope.
And if you can spend a little energy not just determining what makes you feel better when you are beat down, miserable and trending towards hopelessness, and then actually doing those things, you will improve resilience. For me, it’s finding distraction through comedy, seeing great music performed live, being with the people I really love, consuming superior ice cream (yes, bad food therapy, sorry AHA), and, when I’m really desperate, buying a great pair of shoes (yes, retail therapy, sorry Amex). For you it may be something completely different. But whatever it is, it’s ok to take a moment to recover so you can figure out in hindsight that you achieved resilience. It’s ok to ask for help through the darkness. And it’s so important to remember that you have been in that pit before and you climbed out and that you do have the innate skills to do it again when you need to, even if it takes a beat and a small army of supporters. Did I mention the importance of network?
So there, that’s my collective wisdom on this topic. I sincerely hope it helps someone today and tomorrow. As the saying goes, sometimes you’re the windshield and sometimes you’re the bug. So, when I’m in bug mode, I sure hope I can give you a shout and get your knowledge and wisdom, and, if nothing else, a tall pour of Bourbon and a large bowl of ice cream.
Onward!
This whole song is great and has a great and relevant message so worth watching the whole video:

Thanks for sharing encouragement for leaders to take the time and energy to mentor well.
Much appreciated, Jay. L
Brilliant!
Thank you Ginger! L
So spot on and sage advice not only for women, but all of us….
Thanks very much, Eric. I agree! L
Great piece. Okay this might sound dated and goofy, but at about two-thirds into my career, I read “Good to Great” by Jim Collins. Yeah, yeah, I know. Forgetting for a minute that some of the “great companies” he profiled are now gone (like Circuit City), I came away with solid lessons like the “Hedgehog Strategy” and my favorite, the “Stockdale Paradox.” Twenty years later, these lessons are still with me when people ask for advice. I may add to that, “Life is hard. Wear a helmet.” Thank you for always speaking truth to, uh, stuff. – h
Thanks Hank, hedgehog – I like it! L
You keep on giving Lisa. Thank you!
Thanks so much, Peggy – I really appreciate you. L
Thanks for this honest and sage piece. You met me for coffee and connected me to people when I was pivoting roles many years ago – and those intros you provided continue to be valuable in my life. Extremely grateful for your generosity!
Thanks and I’m so glad, Anna! L
Beautifully said, Lisa. Your generosity of spirit is just what we all need.
Thanks very much!
So much here, Lisa. Thanks for another helpful, thoughtful post.
For years, I’ve told our troops that self-confidence is having the judgment to ask questions. So many recruiters nod and pretend they understand what the client is saying, when they should be saying, “Why?” “Tell me more.” “Why not?” “How does your competitions do it?” Etc. Etc.
Then again, as we age we’re just less afraid of looking foolish – or at least I am!
Thanks Jim! L
Thank you for your wisdom and humor!
Much appreciated, Dee! L
Just discovered this blog! The posts are so thoughtfully written, personal and have valuable insights for people early and mid-career. In a world of AI-generated stuff proliferating on the internet, thanks for sharing authentic experiences so openly!
Thanks so much Neal! L
Loved this Lisa! You have a way of writing (saying) what I’ve been thinking…just better. 🫶🙏
Hi Annamarie – probably not better, but I appreciate it! L
Lisa, you absolutely are a bright light in this crazy industry and beyond. You do extend your network when others need it and I have been the grateful recipient of that, so thank you. This kind of support pays it forward and everyone can learn from that example. Love your blog posts – so fresh, so inspiring and honest!
Thanks so much Barbara! It has been too long! L
Appriciation from a delayed reader. Finally read this full article on resilience. Thank you for sharing. It was just the boost, hug, and kick in the pants I needed today.
Jo, so glad to hear that! L