Recklessness

Recklessness. It’s a pretty big word to use when talking about a job search. But when I’m working with a job seeker, it’s a topic that we almost always dance around.

"If I tell my supervisor that I want a raise, they’re going to know that I’m looking for a new job. Because if they don’t give me the raise, then obviously I’m going to leave the company."

Me, sipping tea: "How would you feel if your supervisor knew that you were looking for a new situation?"

"Terrible. They’d fire me right away. They wouldn’t let me put in my two weeks notice. My badge would stop working and I wouldn’t be allowed in the door."

The flow for the “reckless behavior” usually looks like the following:

"I can’t do X. If I attempt to do X, then Y is going to happen. If Y happens, it would be absolutely awful for me."

The most interesting results I’ve seen from job seekers came when they were leaning into the daring, questionable, I-don’t-see-how-that’s-going-to-end-well approaches with their job search.

These were the job seekers who messaged CEOs or created entirely new networks for themselves.

These were the job seekers who identified companies that they wanted to work for and then created posts, articles, and even videos around the problem areas that the companies existed to solve.

These job seekers made effective “bidding wars” between hiring managers, who often wanted the unique skill or niche expertise that the job seeker possessed.

I’ve even seen job seekers outright tell their managers that they were thinking about leaving their organization - and achieved astounding results.

I was in that particular “reckless” category - I woke up one morning, drove to work, and told my boss that I was deeply unhappy with my job. I told him that I needed an increase in my salary and that I was seriously thinking about going to a larger organization that could accommodate this need.

I remember everything about his reaction: his body posture, the way he turned to look at me plainly in the face, his contemplating facial expression.

"I can’t make it happen this month, but I can get the paperwork ready for the first week of June. Is that okay with you?"

"Absolutely," I told him, and then I thanked him and walked out of the office.

My coworkers, who overheard the entire conversation, were staring at me with wide eyes and shocked faces as I sat down at my cubicle.

"He actually said yes?" one coworker asked me in a fierce whisper. "Damn, girl! Can I go in there and do that next?"

The following month, my annual salary went up an extra $2,500. But I have to be completely transparent with you: when I walked into my boss’s office, I had absolutely nothing to lose. I didn’t care if he said yes or no. I wasn’t worried about him firing me on the spot. Whatever the consequences of my actions, I was ready to embrace them all. Because I needed that salary increase, I was willing to do whatever it took to make it happen. And I was fully and completely prepared to dive into a job search if I couldn’t get it from my boss.

This, I believe, is the root behind what people might think of as recklessness in a job search. Having nothing to lose. Embracing whatever happens next. And being ready with the lifeboat if you just need to jump ship.

What are your thoughts on this? I’m curious to know.

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“I will make this happen”

Occasionally, I’ll be talking to a job seeker over Zoom, and I’ll come to a fierce realization: that the person I’m speaking to has the same wild, fearless, break-every-single-rule mentality that is the absolute cornerstone of my being.

When I find people like that, everything changes. I become bolder in my coaching. We push boundaries in our session. And by the end of the call, the job seeker has a roadmap created with an aggressive timeline. They tell me, “Gabby, I will make this happen,” and then off they go.

A handful of weeks go by, and I get an email. It’s the job seeker - only now they’re an employee at the company of their dreams.

I personally don’t believe that anyone needs a specific personality in order to succeed in their career goals. But there’s something about leaning into a bit of recklessness - a bit of daring in one’s approach to the job search - that leads to the most astounding results.

I want to spend time exploring this more in the next email.

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One of the lucky few

I quit my 9-to-5 job and dove into entrepreneurship because I wanted a chance to do something difficult, grueling, and deeply, deeply fulfilling.

I remember reading a blog post by an online business owner. His goal for his readers was to talk them out of pursuing entrepreneurship, listing reasons why this path was the biggest mistake a person could make for their career. By the end of the post, I had a fire lit under my rear like never before. I resolved to be one of the “lucky few” who succeeded in being their own boss.

There wasn’t a person on this earth who could stop me.

It’s happened a few times where a job seeker or career changer grabs a spot on my calendar, telling me that they’re looking to pursue a certain career path. But once we get on the call, the only thing they want to talk about is how to start a business of their own.

I do the same thing that the blog post did for me. I talk about all the exhausting and challenging aspects of my day-to-day. I unabashedly share my shortcomings and outright failures.

It doesn’t matter. I can’t do a thing to remove the glow from their eyes or dampen the fire entrenched in their soul. There’s no fear. There’s only a deep-seated desire to pursue the dream.

I fully understand it. It’s the best feeling in the world.

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Going live on LinkedIn?

I have permission from LinkedIn to use their LinkedIn Live feature, covering whatever topics I’d like to cover (as long as I’m being respectful to the community and platform).

My intention had been to use this opportunity to either start a live stream show or start a video podcast. But the ultimate goal is to use this as a way to have honest and heartfelt conversations with the community on career-related topics.

For today’s email, I want to ask you this question:

Are there career topics on your mind that you wish people would talk about more often? If so, what are they?

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The Power of Myth

I’m looking for ties between Joseph Campbell and Bill Moyers’ The Power of Myth and the emergence of the “follow your passion” approach to choosing careers.

During its time, The Power of Myth was “one of the most popular TV series in the history of public television.” It was released in 1988, not too long after the passing of Joseph Campbell.

I’m reading a blog post by Ron Eisenman, who talks about how The Power of Myth and the idea of following your bliss allowed him to transition from being a lawyer to becoming a teacher within the humanities.

From the Joseph Campbell Foundation:

BILL MOYERS: Do you ever have the sense of... being helped by hidden hands?

JOSEPH CAMPBELL: All the time. It is miraculous. I even have a superstition that has grown on me as a result of invisible hands coming all the time - namely, that if you do follow your bliss you put yourself on a kind of track that has been there all the while, waiting for you, and the life that you ought to be living is the one you are living. When you can see that, you begin to meet people who are in your field of bliss, and they open doors to you. I say, follow your bliss and don't be afraid, and doors will open where you didn't know they were going to be.

The “follow your bliss” ideology was a popular topic among the people who enjoyed the show. Within the discourse of its time, it must have somehow been understood that following your bliss meant transitioning into a career where you could do work that you loved. I’d love to find proof of this.

As a side note… I’m so tempted to watch this show, just for my own curiosity. ;) It reminds me a bit of Carl Sagan’s Cosmos. A few years ago, my sister sent me the link on YouTube where all the episodes of the original Cosmos could be watched. I remember it taking me only a few days to consume the entire thing. Carl Sagan was a beautiful person who created a beautiful series.

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Before long, orders were pouring in

Learning about Richard Bolles and reading his interviews has been a truly enjoyable time. I can't help but feel a bit sad in knowing that he's passed away. There are so many questions that I'd have loved to ask him if I ever had the opportunity.

Today, I just want to highlight a portion of text from an interview with Fast Company.

But as it turned out, Bolles himself was one of the bailers. As an ordained Episcopal priest, he was canon pastor of Grace Cathedral in San Francisco. But he lost his job in a budget crunch. He then landed an administrative position with the Episcopal Church, meeting with campus ministers at colleges across the country. He discovered that many of these ministers shared his predicament: Their jobs were in peril, and they had no idea what to do.

So Bolles did some research and wrote a 168-page guide to help the campus ministers he was supervising find jobs and change careers. Stuck for a title, he remembered his wacky question from two years earlier. He self-published the book in 1970. The first pressrun was 100 copies, which Bolles toted to a meeting in Philadelphia and distributed free of charge. Then something extraordinary began to happen. He started to get orders — first for 1 or 2 copies, then for 40 or 50. Before long, orders were pouring in — not from other ministers, but from such institutions as General Electric, the Pentagon, and UCLA.

What an amazing person.

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Work you love

I’d love to get my hands on the very first commercial version of What Color is Your Parachute, published in 1972.

I was given the 2021 version, and I was honestly excited to read this particular edition of the book deemed “essential” to anyone contemplating a career change today. My reason? The pandemic. I wanted to know if the 2021 edition had anything to say taking COVID-19 and our new #WFH culture into consideration.

So, why do I want the 1972 version? The 1972 version was considered “radical” to readers of the time. (I’d love to find copies of the actual reviews which allude to the radical nature of Richard Bolles’ ideas.)

It was this book, coupled with the work of Joseph Campbell in the ’80s, that led to the development of a novel and intriguing idea in the career space: that the key to career happiness was to follow your passion.

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Within my role as a career coach, I’ve had many sessions begin with the question, “Gabby, how do I find my passion?” We can have an incredibly productive session from this starting point. I believe there’s nothing wrong with contemplating questions like this.

Roughly seven years ago, I discovered Scott Dinsmore’s impactful TEDx Talk, “How to find work you love,” through an email sent to me by a coworker. His talk, combined with his Live Your Legend philosophy, propelled me down the path that brought me here today.

Had I not allowed myself to fall into the romanticism of “following one’s passion is key to doing work that you love,” I’m certain that I never would’ve left the pharmaceutical industry. Within continuous disappointment, disbelief, resignation, and then deep depression, I clung to the last scrap of hope that I could find: that I hadn’t made a terrible mistake and that I wasn’t trapped in this profession. I just hadn’t found my passion. Once I knew what my passion was, I could figure out what work I needed to be doing in order to be happy. Then I could get a plan together and begin the process of starting over with a brand new career.

You’re seeing me write about a few unquestioned assumptions in the career space. One of those assumptions is that a career change is hard. Another way to think about it: we rarely hear that a career change is “easy.”

I’m writing about this, because I believe it’s very healthy, and very important, to consider these assumptions as plainly as possible. A study into the origins of modern careers feels like the right starting point for this topic. Understanding the history of the “career” and its foundation, systems, and pathways will, I believe, be instrumental in us shaping our careers to be what we need them to be.

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Your responses: “Making a career change is hard”

In my quest to answer the question, “Why do we never hear that a career change is easy?” I’ve found a resource that I’m so wicked excited about. There’s a textbook (collection of essays?) titled Origins of the Modern Career that I want to access. The book was created as a sort of response(?) to a conference on “Employment Security and Career Mobility in Historical Perspective” back in 2001. We can read the first chapter online through ResearchGate, but if we want the rest, we have to get the book. ;)

Going back to our original question, I’ve received a number of wonderful comments that I want to highlight here:

”Career change is ‘hard’ to some because people end up outside their comfort zone. Whether it's a R&D scientist switching to PM to career coach to earning a MBA, it's not easy to get out of the comfort zone. However, when you are uncomfortable, you learn the most and unlock your true potential.”

”I believe there is an expression anything that’s hard is always worth the effort because you know nothing really comes easy!”

”I remember when a math teacher told me to stop saying Math was hard. It wasn't hard it was unfamiliar and different and I'd actually have to put in work to learn it. We often associate things that are hard with things that have a learning curve, and things we have to actively learn.”

”Changing your career means a completely new skillset, an entirely new network, and an unfamiliar ecosystem, with no certainty that it will actually work out.”

Is there anything that you’d like to add to the conversation? I always welcome your insights and feedback.

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Origins of the modern career

Before you read this email, I’d love for you to spend a few minutes with Cal Newport in his blog post, “Ancient Complications to Modern Career Advice.”

It goes beautifully with the question we’d like to answer: why do we believe that career change is hard, and why do we almost never hear the opposite, that career change is easy?

Cal Newport’s post had me asking questions about careers in general, and it led me to a chapter of a textbook on the origins of the modern career. (I might be buying this textbook - wow, I forgot how expensive they can be!)

While I’m trying not to make any judgments right out the gate, I do have a few ideas floating around as to why the assumption exists that career change is hard.

1. Career change is expensive - both to the employer and to the employee.

2. Career change is taxing - mentally, emotionally, and energetically.

If you have any ideas floating around yourself, please hit reply and share them with me.

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Making a career change is hard

I received a few replies to my last email. They were raw and very, very honest. I deeply appreciate you guys for sharing your truths.

I have so many things planned for the next couple of months. Plans for daily email writing. Plans for revamping the website. I still wonder if I’m biting off more than I can chew, working on these things while getting ready for a move to Florida.

Roughly half of the house is packed away. This coming Monday, the rest of it will be gone. The following Monday, I will be packing a few boxes of pots and pans, a suitcase of summer clothes, and my cat’s things into the car.

And then off I go to start a new life.

We believe that making a career change is hard. We hear the word “hard” and it’s as if a curse has been released. A barrier is immediately created, and it stops us from making any kind of forward movement.

I want to spend a bit of time exploring this subject. Why do we believe that a career change is hard? And why, specifically, do we almost never hear that making a career change is “easy”?

I have a few articles saved in one of my bookmark folders that might be fun to dig into as a starting point. Stay tuned. :)

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If you could have anything

Today’s email is a short one. It’s a question that I’ve asked every single job seeker that I’ve ever worked with:

If you could have anything at all - and if there were zero consequences attached to having it - what would you like to have?

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The internal demons we battle

To help me write this email, I’ve opened up the history page on my appointment scheduler, showing the different coaching sessions that I’ve done over the past two years.

Each person on this list came to me for a specific purpose - to talk about a new career goal, job-specific pursuit, etc.

But instead of covering these topics on the call, we would let ourselves go a step deeper.

”I’m trying to become a physician assistant,” would become, “I want to make my parents proud.”

”I’m looking to transition into a director-level role,” would shift into, “I just don’t want to embarrass myself.”

”I want to be a software engineer for Google,” became, “I need to make the ‘right’ next move in my career.”

I titled this email, “The internal demons we battle,” because it’s rarely ever about the goal. At the heart of the problem, we’re trying to solve an internal struggle with what it is we truly want.

And maybe achieving the goal will calm that struggle. Maybe getting the job will be what solves the overarching problems of our life.

But the takeaway is that the goal we’ve set for ourselves usually sits at the surface of something bigger.

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“My goal is to…”

I can’t remember when I started doing this. But at some point, I created a note on my computer, and I began to paste the messages that people would send me whenever they wanted to schedule a career coaching session.

• I would like to open my vision to where I can step ahead and explore the opportunities that I’m probably not seeing around me. Building a network also would help me.

• My goal is to find a Data Analyst position

• My goal is to pursue my passion for research and find my dream job, where there is opportunity for advancement.

• My goal is to transition from teaching to a field more suited to using my bachelor’s degree in physics. I also need to relocate near my family/ in-laws. I will stay in education if it is an opportunity better than where I currently am.

• looking to effectively market myself, looking for a new job

• My goal is to eventually transition from a UX management role to director or lead position by learning the right skills, strategy and tactics.

• I am pursuing an MBA with a major in Finance graduating in May 2021. I am also pursuing CPA. I need a coach as I am looking for a new job in the field of accounting.

• Am looking for a career change, need help in preparing for interview. the role which am planning to take on is Sr. Tech program manager. any advice on how to prepare my profile, interview etc.

• I'm working on completing my EdD in STEM technology education. I need to explore what my options might be in the corporate world.

I’ve always found the patterns in these messages to be fascinating.

There’s an endless list of reasons why we get to a point where we want to have a conversation about our careers. Sometimes, it does start with our goals or desired pursuits.

But I’ve come to find that there’s usually a second, much more personal reason for seeking career coaching.

I’ll talk about the internal demons we battle in the next email.

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A private conversation

It starts with a soft ding! notification on my phone. I open up the LinkedIn app, click on the icon to access the private messages, and I see the beginnings of a note.

It usually follows a certain pattern:

Hey, Gabby. I hope this message finds you well. I’ve been following your posts for some time now. I read your most recent post, and I see that you’re offering free career coaching this month. I’d love to take you up on your offer if it’s still available.

I respond by sending over a link to my calendar, and I wait to see which time slots the person ends up picking.

If they choose a slot within the week, I can often predict the tone and flow that our conversation will take. The person will usually have very little reservation in sharing what’s going on. We plot and scheme and brainstorm to our heart’s content. The person usually walks away with several pathways mapped out that they can then explore.

If they choose a slot much later in the month, that’s when things take on a slightly different character. The person will be glad to join me in the Zoom session, but there’s a subtle, almost protective aura present. The person wants to take this step, but they’re a bit unsure of what it is they want to say.

It’s a brave and difficult thing, talking about our career journeys.

My job is to create a space that’s safe, private, and free from any form of judgment. It’s also my task to make sure that the person sees the session as an event with zero consequences. They can say whatever it is that they need to say. They can express themselves however they like. I will never force them to make a decision, and I will never set any expectations for them to follow-through on.

I bring just one goal with me to the session - that they will be fully comfortable being themselves. I ask questions that will stretch their thinking. I give them things to contemplate. When the call is complete, I invite the person to come back whenever they like.

I don’t think of these sessions as career coaching. Rather, I see these as a private conversation between two people, where we can say what we’ve been wanting to say for years.

I believe that we live in a kind world and that much of this kindness is visible through the actions we take for each other. But there’s kindness in listening, and kindness in creating welcoming spaces, where we can do a much better job in placing our efforts.

In the next email, I’m going to sift through the reasons why we get to a point where we want to have a conversation about our careers. It’s a long list - but a few themes stick out that I believe are worth the time to explore.

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Making bread

I just finished mixing ingredients for an overnight “sourdough-esque” bread. Tomorrow, I’ll form a few loaves and bake some beautiful, fragrant bread.

I was worried for a moment that I’d made a terrible mistake, cutting off two income streams and deleting most of the pages on my website. But today, I had three resume clients approach me for work at the end of February and early in March. The proposals are all solidly written, and there’s one, in particular, that’s highly unique and really interesting.

I think that I’m going to be just fine.

My next set of emails will be going down a new road. I’m going to be talking about career coaching - the experience of joining me on a Zoom call to chat about what’s going on in your career. I have a rough outline prepared for what I want to cover in the next five emails. I’m surprisingly excited to write these up.

Are there any career-related topics that you’d like for me to cover in the next couple of weeks? I always welcome your input - just hit reply.

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I broke my business

Well… I’ve gone and done it now. ;)

Just kidding. I didn’t break my business so much as I’ve temporarily taken down web pages and removed sections in my LinkedIn profile.

I’m getting ready to make a pretty significant shift in the way that I do my work. I’ve been planning this for some time now, but I just couldn’t find the stomach to take the plunge.

My business is working. My clients are happy. I’m making enough to pay all the bills.

But at the end of the day, I’ve built something that won’t take me where I want to go. :)

So! Where does all of this leave you guys?

The Resume Writing Package and LinkedIn Mastery Program are both still here. If you want to take advantage of either of them, all you’ll need to do is send me a message.

Eventually, the day will come when I’ll only be taking on new resume clients through the Fiverr Pro platform. LinkedIn Mastery will become an 8-week interactive workshop instead of a 1:1 intensive program.

I’m planning to evolve into an independent researcher on the career progression landscape that will emerge out of this pandemic. I’m already seeing a number of things happening, and I want to be there in real-time as they happen.

I want my clients to win. I want them to succeed at whatever goal they place in front of them. And I hope that you’ll believe me when I tell you how incredibly hard it is to make these changes, and how much love I have for all of you.

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Impact of remote work

Today’s email is pretty short. I have a link to a quick video from the WSJ: “How Tech Companies Are Revamping the Remote-Work Experience.” It’s an interesting piece on the impact remote work can have on innovation and productivity. The ways that the companies in the video are tackling these challenges are pretty creative and (I think) worth exploring deeper.

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Thrill without setting expectations

Aha! is a company that’s been entirely distributed since at least 2014. Outside of their service offerings, they seem to position themselves as a thought leader in the remote leadership space. I’ve spent a lot of time within their blog this past month.

They came out with an article a few days ago on how to thrill people/clients/colleagues without setting any expectations at the onset of an engagement. I smiled at the word “thrill” when I read it.

I’ve been digging into the idea of creating an “experience” of us as remote professionals for our colleagues, supervisors, and senior leaders to encounter and appreciate. The ultimate goal would be to maneuver us for a promotion, cultivating a reputation for the skills and values that management wants in their remote leaders.

What’s fun about the Aha! article is that it feels more like a lesson in effective communication than in being thrilling… but I understand what they’re going for. Delighting a customer by making them feel heard and understood is the key here. If we set expectations for them at the onset of a meeting, we can dampen the “experience” (my word) by putting restrictions and barriers around what a customer should think, feel, or expect from us.

The more I read The Experience Economy, the more examples I see in everyday life of this concept. But I also recognize how easily a book can influence a person - especially with one as engaging (and validating) at The Experience Economy.

And so, dear reader, this leaves me with a question for you.

What are your thoughts on all of this?

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Progress

At the beginning of this project, I took advice from an amazing and incredibly thoughtful person who’s in a TEI cohort ahead of me. I created a centralized place for all of my raw notes as I research promotions in the age of COVID-19 and #WFH. I promised that I would maintain it and contribute to the notes in real-time as I worked.

Today, I found a paragraph that I typed roughly a month ago. It was just a blurb that I had floating around in my brain.

Landing promotions within our newly-remote companies could necessitate a change in the way we present ourselves virtually and the “reputation” we cultivate within our remote teams.

As I read The Experience Economy by Joseph Pine and James Gilmore, and as I look through the notes, articles, and interview answers I’ve compiled, it’s amazing how many dotted lines seem to be appearing for this idea.

”A change in the way we present ourselves virtually”: seems to go perfectly with evolving our leadership style for our new remote work environments.

”A reputation we cultivate within our teams”: this is the “experience” of us that we want our colleagues, supervisors, and senior leaders to encounter and appreciate.

I want to test this somehow. It’s one thing to dig at this idea and write about it. But I want to see if there’s actual substance to it.

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Safe enough to be vulnerable

One of my connections kindly shared an article on the leadership traits prevalent in successful remote leaders. It’s been sitting in my pile of raw notes, and I finally found the time to take it out and give it a thorough reading.

Valentina also left me an insightful comment on the topic.

Summarized, the traits that make a leader effective in a remote position are:

• Connected — coordinates and directs people, helps work together

• Aware — keeps the pulse of work progress, monitoring

• Organizer — sets, prioritizes, manages tasks

• Productive — applied intelligence, gets things done, goal-reaching

• Good writer — good written skills, detailed, sophisticated

It all comes down to conscious and visible communication both around keeping people together as well as ensuring that things get done. Where in-person charisma and being able to talk to people is more important, in a remote setting it's all about open communication - open as in where it happens and how it happens. It's a much more risky proposal since writing down an opinion feels more final than "just" talking it through and adjust as you see others react to it. There's no "I didn't say it" when you wrote it down. ;)

Open communication is a tough and weighty thing. I think of it as a skill that can be practiced and cultivated.

I also believe that open communication is a heck of a thing to ask of another human being.

Open communication requires vulnerability - the kind of vulnerability that allows a person to speak their mind, share their opinions, and express themselves as they see fit for the situation.

We can’t be vulnerable if we don’t feel safe. And I wonder if our remote working environments are places that feel safe enough for us to tap into our vulnerable sides.

This is a big question to ask, but do you feel safe enough in your remote work environment to speak your mind? Share an opinion? Express yourself as you see fit for a given situation?

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