Ending with Intention: Once a Geek Whisperer with Amy Lewis (2/2)

Nerd Journey: Career Advice for the Technology Professional

How do you know when to stop doing something you love? Amy Lewis would say decisions like these require us to be intentional about putting something down so we can pick up something else.

Amy is an unapologetic marketer working in the tech industry, and she was once a Geek Whisperer. This week in episode 302 we explore the genesis of Amy’s involvement in The Geek Whisperers podcast. You’ll hear how it all began, how it changed over time, the overarching purpose, and why the show eventually ended. Amy speaks to the need for intention in our decision making, shares advice for those in our industry impacted by layoffs, and we learn how Amy progressed into people management. For the prospective or current people leaders out there, listen closely for some great tips.

Original Recording Date: 09-19-2024

Amy Lewis is the director of enterprise marketing at GitHub. If you missed part 1 of our discussion about Amy, check out Episode 301.

Topics – Whispering with Intention, Advice for Those Impacted by a Layoff, Pursuing People Leadership, Parting Thoughts with a Geek Whisperers Twist

2:31 – Whispering with Intention

• As big fans of The Geek Whisperers podcast, Nick and John ask Amy how it all began. Nick remembers finding this podcast in 2016 / 2017 and how he couldn’t stop listening.
  • The hosts of The Geek Whisperers were Amy Lewis, John Mark Troyer, and Matt Broberg.
  • Amy likes to make her own luck and will jump in when she sees certain circumstances. In the case of The Geek Whisperers, Amy feels there was a lot of good fortune.
  • John, Matt, and Amy knew of each other and were running similar programs at different companies.
  • Amy thinks John and Matt had been talking about a podcast idea and knew each other a little better. Amy remembers first meeting Matt at a VMworld conference.
  • The original purpose of Amy, Matt, and John getting together was to talk shop. John had a great editorial vision for what could be a podcast.
  • “Everything just kind of disappeared into a group effort. It was magical…. It was just this amazing synergy. And when we first started we really did talk shop. It was a lot of influence marketing. It was about programs we were running. It was a time where influence marketing in a B2B setting was unheard of…. And then there was a moment where we realized so many people were hungry for hearing stories of career, and we decided to pivot. It’s a passion for all of us, and we started to tell the stories that people kind of couldn’t get another way, ask questions that other people might not be able to ask, share stories that we’d overheard or connections that we’d had…. We did what we hoped to do – create a body of work that we hoped would serve a community we really loved and were proud to be part of.” – Amy Lewis
  • Nick remembers Amy’s mention of listening back to past episodes of The Geek Whisperers to help herself fall asleep.
• How do you decide to lay something down that you really enjoy and is very successful (i.e. The Geek Whisperers)?
  • Amy says they found a natural stopping point in terms of number of episodes and in what year.
  • My re-iterates how difficult it can be to produce weekly content. She remembers heavy travel and doing food blogging while still being part of the podcast.
  • Amy would help on the editorial side of the show, while Matt and John would often do editing and write show notes. Looking back she wonders how the 3 of them kept it going when they were all so busy.
  • “We didn’t want to fade away. We wanted to end strong, and we wanted to do it with intention…. That was a shared agreement with the 3 of us. So we stayed in while we were in, and we all agreed when we were out. And it just kind of speaks I think to the synergy of the group…. We didn’t know what was going to happen day to day. We just really enjoyed talking to each other, and it made sense to record it. Then suddenly it became a thing. And there is some pressure. It was hard. We had hard days and we had days where we were tired and really had to gut it out. And we really kind of found our groove. I don’t know. It just had a natural lifecycle. It would be hard even with retrospect to know. So no, we didn’t know where we were going to end when we started, but we knew when it was time. And I think all of us feel really good about that.” – Amy Lewis, on being part of The Geek Whisperers
    • Amy says they did not know where it would end when they got started, but it is amazing to think about how many people the podcast mattered to.
  • John mentions this idea of retiring something while it’s still good.
    • “It’s ok to put something down because it means you get to pick something up…. I think until you make that commitment to symbolically put something down you don’t make space to pick something else up.” – Amy Lewis
    • Amy highlights mentoring a number of women related to maternity leave and how to bring family into their career lives. Going on maternity leave forces hard decisions because life is different before compared to after. This example works well to help people understand they have to choose to put something down to pick something else up.
    • Intention means laying something down and being ok with it. Amy highlights the importance of being intentional when we think through choices.
• Amy says we often feel things happen to us. And right now our industry is being obliterated with layoffs and career choices being made for people.
  • Amy mentions she has been part of workforce reductions and understands what it is like.
  • “We have to where we can bring intention into our career and life and direction…. It’s important to figure out what you’re going to stop doing so you can start doing something else.” – Amy Lewis
  • Part of intention is setting boundaries and understanding our preferences (likes and dislikes). And intention is needed to put something down to allow for picking something up.
  • We can’t learn a new skill if we’re too exhausted, for example.
• John says doing things that are valuable probably aren’t easy. To increase your value likely means picking up something else that is difficult. It is almost laughable that we can maintain everything in our lives that is also difficult when we try to pick up something new that is difficult.
  • If someone other than you said they were going to do this, you would caution them to reconsider and help that person understand what they are trying to do is not sustainable.
  • Amy gives the analogy of a weight lifter at their max and then adding more weight. It’s going to be an injury.
• Amy highlights the finite nature of publishing. After each book, there was a delineated stopping point. After being in online marketing, she feels more like Sisyphus pushing a rock up a hill
  • “Even if it’s fake, we have to create moments of celebrations and endpoints, and this is the same concept, which…makes tons of sense to us in all other aspects of our lives. But somehow we burn ourselves out in career, particularly in technology…. The joy is there’s always something new, but we’re the ultimate push the rock up the hill. What’s our endpoint? The pixels don’t end. Where is the edge of the internet?” – Amy Lewis
    • Working from home can make it hard to have a defined stopping point.
  • Don’t worry – Amy can feel your pushback as you listen to this.
    • “You have to choose for yourself. I strongly recommend it. It’s good for mental health. It’s good for longevity. It’s good for all the things. Decide where some of your parameters are. Decide what wins look like. Decide what the outside edge looks like. And decide very firmly. Be brave. Be bold. Put something down to pick something up.” – Amy Lewis
  • John has a team member who speaks about only having a finite number of tokens to spend each day on work and other parts of life.
    • “If you’re not making a choice, a choice will be made for you. Sometimes it’s your body that will make the choice for you.” – John White

14:57 – Advice for Those Impacted by a Layoff

• “Our best work doesn’t come under duress. It comes in those quiet moments.” – Amy Lewis
  • The reason we get ideas in the shower is because we stopped thinking about it. This applies to careers too. This definitely applies to those listening who may be in transition and are thinking about what they plan to do next.
  • When a choice is made for you, all you can focus on is what your next choice will be. It could be you want to gain or learn a new skill. Perhaps you want to intentionally take a break.
    • Amy found it very hard to take this advice.
    • In one of her last transitions between roles, Amy negotiated her new job offer so that she had a small gap of intentional time before starting work.
    • You can give something up to get a short break between jobs as part of the negotiation.
    • Amy encourages us to think of things we can control in these types of situations.
• If someone listening has been laid off or lost a job, what are some ways Amy has found to get past the hurt, angst, and shame of such an event?
  • “If you think that other people don’t hurt and that you’re broken because you do hurt, just hear me say, ‘it stinks. It always stinks. It is painful grief.’ Don’t try to power through that. Write it down. Say it out loud. Talk to people. But sometimes just the very act of acknowledging and saying, ‘that is terrible and I feel terrible and that makes me feel terrible’ is one of the first things to kind of get through it.” – Amy Lewis
  • Amy tells the story of being part of a division that was laid off. Even though they knew it was coming, that event happening was terrible. So many people in our industry are going through this.
  • “Know you’re not alone. And know that you’re not weak, bad, or failed. And this is not the end…. Like with any grief process, don’t try to make it be better immediately…. It is going to knock your confidence. It’s going to feel bad. It does feel bad…because at its root, a choice was made that you didn’t get to participate in. And that is terrible.” – Amy Lewis, on advice for those processing a layoff
  • For every story of hurt and awful things like layoffs, Amy sees turnaround stories. She appreciates people telling the stories of life after working at a certain company.
  • John mentions we often discount the effect of our human emotions as technical people, often expecting ourselves to react to facts instead of giving the grace to ourselves to react emotionally. We can think the emotion reaction doesn’t make sense and spiral out of control.
    • We don’t often realize our bodies have to go through the emotional processing of what’s happened. The facts don’t just win out over everything.
    • Amy mentions the fear people have about the rise of AI or generative AI tools. Code may be deterministic, but human language is non-deterministic. We gravitate toward what is safe and predictable (i.e. the beauty of technology is its deterministic nature). It’s very unsettling to have an illogical thing happen.
    • Amy believes our human ability to make rational choices in irrational spaces implies we will be able to use tools like generative AI without being mastered by them.
    • “The thing that makes us more able to compete is also the thing that’s going to make us hurt.” – Amy Lewis, on being human
    • Amy had a friend who once said, “sometimes you just can’t square it.”
    • When we are people who work and live in worlds of logic, we have to admit things do not make sense. It can be freeing to admit something makes no sense, allowing you to do what makes sense for you.
    • Amy sees people re-skilling and applying for jobs differently. She feels like our industry will rebound.
    • New jobs will likely appear in different ways. How work is going to be will change, and the jobs available will change.
    • “I am an optimist, and I don’t think it’s over. I think we have to decide what’s next.” – Amy Lewis, on the golden age of tech and how our industry looks moving forward
    • John reiterates that there is going to be immediate short term pain when you’ve gone through job loss. It can destabilize one’s identity or hurt your self-confidence. John doesn’t think there is an easy way to look at the macro view in that situation.
    • “Sometimes when you’re in a hole, it just takes somebody else to go, ‘the hole is not bottomless. There’s nobody who is making the hole deeper, and here let me help you understand how to get out of the hole.’ Sometimes you just need to lean on an outside perspective…. I need somebody to tell me everything’s going to be ok so I can just trust that. And that will help me keep on going.” – John White
    • Amy hopes the above can be an outcome of this podcast. If you are employed, reach out to someone who needs that encouragement right now. Amy says she had the benefit of someone reaching out to her with encouragement during a difficult time.
    • “So if you’re somebody who’s feeling ok right now, I would just challenge all of us to reach out to someone who you think may not be. Check in on them, and give them that encouragement. Give away something because you’re going to need it someday…. Nobody rides this ride without hitting the whammies at some point.” – Amy Lewis, on encouraging others
    • Amy is Geek Whispering to us during this podcast.

24:34 – Pursuing People Leadership

• What made Amy want to pursue people management, and how has she helped others determine what they want to do next?
  • Amy tells us it feels like people management was inevitable in her career. When we was in publishing, Amy invented an unpaid internship that she later convinced leadership to fund as a role.
  • In total, Amy ended up with 7 or 8 interns, and most of them went into publishing as a career after the internship. She was willing to teach them and help move their career forward. Amy tells us she has stayed connected with these folks over time.
  • “I think that’s where I first got a taste for connecting people with opportunity. These were incredibly bright people, so I in no way, shape, or form get full credit. But I knew how to open a door, and I really always believe in opening a door where I can.” – Amy Lewis
  • Amy became a people manager and a director at the same time and developed a habit of inheriting teams due to various circumstances.
    • She likes managing people and can often see connective tissue where others don’t.
    • Amy shares an anecdote from her time at Solidfire. After coming back from vacation, Amy had been placed in charge of field marketing and was told that her CMO had hired someone new. Though surprising at the time, Amy says it turned out really well.
  • People management is hard and is very different from being an individual contributor.
    • “Quickly, whoever reports to you will be better at their job than you, and that is the way it should be. You should help them be better at their job, but that does not mean necessarily on point expertise. They are going to be better experts because they are putting in 8 hours a day. Their seat time will always exceed yours. So you have to genuinely enjoy the HR side, and the HR side is really hard…. It is a hard job. You have to be ready to support people. You have to be ready to do hard things…. If you do not enjoy people, do not do it.” – Amy Lewis, on people management
    • Managers have to deal with people’s personal trauma. This could mean an employee has a family member with cancer, wants to quit, or needs to be fired. Someone once told Amy one of these things is almost always true when you’re a manager.
    • Amy emphasizes the need for managers to take courses, read books, listen to podcasts, and do HR training to gain greater managerial skills. It’s part of the job.
    • If the hard things don’t sound fun for you, people management is likely not for you. We also do not have to manage people to progress in our career.
  • As a first time people manager, Amy’s comments resonated with John.
    • It might be more difficult for a high achieving individual contributor to step into the role of people manager because of the temptation to encourage people to do what they did.
    • Amy says sometimes people managers end up competing with the people reporting to them! The people manager has to accept that they will no longer be the expert like their people will.
    • John shares a story of being at a sales kickoff and being required to attend a session on becoming a better technical manager rather instead of a session focused on a new innovation.
  • “It is truly putting something down to pick something up.” – Amy Lewis, on people management
    • Amy has had player / coach roles, and these are more like a job and a half with a large team.
    • These kinds of positions require you to make strategic choices about what you will and won’t do. There is no way to do it all.
    • Every company is different, but Amy likes the fact that John’s leadership redirected technical managers to get better at their craft.
    • “We had several of these conversations during the Geek Whisperer days. I applaud folks who tried management and decided they genuinely got more joy in their life from not managing people, and I think that’s ok too. I know plenty of people with successful career trajectories on every single combination of that – people who manage people, people who managed people and stepped out of it, people who never want to manage people and are very open about it. I applaud a world we live in where all those ways of being can be celebrated.” – Amy Lewis
  • When Amy first became a manager she was terrified, admitted it, and went to get help immediately.
    • Amy is thankful people were willing to save her from what she did not know.
    • New managers should seek help in the form of a mentor, reading books, etc. Do many things to get help.
    • The new people manager / leader is going to make mistakes and will have to learn how to forgive themselves for it.
    • “I’ve had the fortune of running a few just incredible teams. Teams that give you grace to fail and grow with them is such a gift. So the number 1 thing you can do is build trust. And say what you know and say what you don’t know.” – Amy Lewis
    • When Amy inherited the team at Solidfire, she had never run field marketing, the people knew more than she did, and she had no budget. Amy showed up to the first meeting with that team and was open and honest about what she had and what she didn’t have. She would elevate their work, remove barriers, and established herself as someone the team could be honest with.
    • “From the flip side, if you decide you do this and you get all in…build trust and tell the truth with that team, and encourage them to trust each other. And if people aren’t ready to be in that boat rowing along with you, then help them find the next opportunity.” – Amy Lewis, to those thinking about becoming people managers
• Did Amy have to learn how to do 1-1 meetings with her employees after becoming a manager, or did it come naturally because of Amy’s previous experience?
  • Amy says she wanted to hide from it, and she has seen new managers ignore the power of the 1-1. Now, Amy is adamant about having 1-1s with her people.
  • Some of the episodes Amy, John, and Matt get asked about the most are the ones with Dom Delfino. Dom is a mentor of Amy’s.
  • “One thing about getting a mentor like Dom or any good mentor…they are going to tell you things you don’t want to hear probably immediately…. I knew I didn’t know field marketing, but I thought that somehow being a good human and having good sense was going to save me…. If you prioritize your 1-1s with your people, other things with take care of themselves. You’ll figure the rest out…. I am a story of what not to do. Do not run from your 1-1s. They will catch you.” – Amy Lewis
  • Dom Delfino told Amy the most important thing a manager can be doing is having regular 1-1 calls with their employees.
  • Amy highly recommends checking out the Manager Tools podcast series for those just getting started.
    • This podcast covers much of the basics and is a great refresher for anyone, regardless of skill level. John says Manager Tools has been extremely valuable to him as well.
    • The same group also runs a show called Career Tools, which has a lot of great content on writing your resume, doing a job search, etc.
    • John mentions one of his teachers encouraging him to do the basics better to really progress. It wasn’t about advanced techniques. It was about doing the basics better.
  • If you are someone who is between things, you can train for the job you want next.
    • “You don’t have to have a team to train for the team you want to manage. Go in there and listen to it and get yourself ready so that when the opportunity finds you, you’re ready.” – Amy Lewis, on the Manager Tools podcast

37:45 – Parting Thoughts with a Geek Whisperers Twist

• It was Amy’s idea to have a little fun and ask her the familiar closing question from The Geek Whisperers. What’s one thing in career Amy would never do again in her career?
  • “I’m such a positive person, but I learn through negative space.” – Amy Lewis
  • Amy says don’t move for the title, whether that means relocate, change companies, or both. Avoid letting the appeal of a title lure you somewhere.
    • Being able to make a move does not mean you should make it.
    • Looking back, Amy feels there were a couple of times where she didn’t look carefully enough before making a change. In other instances, Amy took a necessary pause to truly examine if something sounded too good to be true.
    • “One of the things that’s a cheap and easy sell, particularly in this time where things are so chaotic, can be the lure of a high flying title. And I would say the corollary is probably don’t ignore what may sound like a title that’s ‘beneath you.’ Set that aside and really look at the work you’re doing every day and the people you’re doing it with and the people you’re reporting to. So, if you get glamoured, the title is the easiest thing in the world to change…. You will not be made whole by that title…. Don’t ignore or overlook something that you think is beneath you, and don’t get lured by the glamour of something that sounds amazing.” – Amy Lewis
    • Listen to Amy’s analogy about the Moody Café and how it relates to jobs and job titles.
  • John says this sounds a lot like career progression isn’t the only thing in the world. We should assess if a particular job is something we should do and if we’ve already spent all our tokens.
    • “Progression can mean what you would like it to mean…. You said it beautifully in terms of consider how many tokens you’ve got, and consider what makes you happy and really fulfills you. Look at the work. Look at the people. Look at the management chain. The title is the most fluid thing of all of it.” – Amy Lewis
    • And remember. you may have to lay something down to progress.
• If you want to follow up on this conversation with Amy, you can contact her:
  • On LinkedIn
  • On Threads – @amylewi

Mentioned in the Outro

• Nick thinks “once a Geek Whisperer” might not be an accurate description of Amy Lewis. Maybe it should be more like “still a Geek Whisperer?”
  • Nick recently realized while editing this episode that he still had episodes of The Geek Whisperers downloaded to his phone and was able to listen to them again. Amy, John, and Matt had an amazing chemistry that welcomed you as a listener, making you feel like you were in the discussions with them and learning with them. They were also welcoming to Nick when he was a new member of the same technical community.
• The Geek Whisperers as a body of work led to new opportunities for the hosts (Amy, Matt, and John). What the your body of work that makes you stand out?
  • Maybe it isn’t a podcast, blog, or video series. How are you making an impact inside your company or outside it whether paid to do it or not? How are you serving others in the same way Adam Grant describes in Give and Take (the idea of otherish giving)?
  • Keep documenting your accomplishments, community service, your hobbies, community service, etc. All of these things can help us build a body of work. If at least the documentation of your body of work is publicly accessible it allows people to see a little bit of who you are before they talk to you.
• When working on a project, remember things have an endpoint. Being intentional means you might have to make the choice to put something down due to circumstances in your life so you an pick something else up. Don’t be ashamed or afraid to keep re-evaluating over time.
  • In Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3), Max tells us he thinks about how he will hand off a project before he starts it. Maybe you don’t think about it at the beginning, but you can regularly re-evaluate your involvement as part of being intentional.
  • For another discussion of being intentional, check out Episode 165 – Excel by Being Intentional with Andrew Miller (1/3).
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page for an aggregated list of our most impactful conversations on the topic.
• Amy has also recently launched the Unicorns in the Breakroom podcast with Sarah Vela – a podcast to help you figure out corporate life.
  • Unicorns in the Breakroom on Apple Podcasts
  • Unicorns in the Breakroom on Spotify

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [e-mail]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
• Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_