When the road ahead isn’t clear

In 2012, I was sitting in my office at Deutsche Bank, dispirited and disillusioned, wondering what I could possibly do to alter the downward trajectory of my career.

I had a few ideas. I toyed with a startup idea, had begun exploring a topic called “working out loud”, and recently started a blog. 

But what should I do next? Should I try to make the most of my job? Quit and try something new? Do some other kind of work on the side? 

I didn’t know.

Climbing the hill (with your head up)

Around that time I was reading a book called Running Lean aimed at helping startups deal with uncertainty. (The idea for a Lean Canvas comes from that book, and I’m re-reading it now for reasons you’ll see below.)

The book contains a rather arcane reference to a search algorithm that can apply to startups—and also to careers. I dog-eared the page with this text box.

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The author’s conclusion underneath helped me see what I should do next.

While there is no way to completely avoid the local maxima problem, you raise your odds for finding a better solution when you are initially open to exploring and even testing multiple models in parallel.

Making it through the fog

That was it! Instead of just “climbing the hill” at Deutsche Bank, or risking everything to leap onto another hill, the key was to follow multiple paths and remain open to possibilities. So, while I tried “local optimization” in my current job, I also did small experiments with other topics and kinds of work. 

Some of those experiments (like designing an app) turned out to be dead ends. But they didn’t cost much and I learned a lot, so they were still good investments. The experiments related to Working Out Loud led to a book, tens of thousands of people in WOL Circles, and a new fulfilling chapter in my life.

A practical way forward 

Just today, someone wrote me to say that he’s challenged by a situation similar to the one I faced eight years ago. He said he’s looking for a clear path ahead for his career and doesn’t see one.

But do any of us see a clear path ahead, especially now? 

I replied that I still don’t know exactly where I’m heading (which is why I’m re-reading that book). The best we can do is to think of our aspirations and intentions as a kind of compass, not a map. You take a small step, look around and explore and learn, re-check your compass, then decide on a next step. 

The person who wrote to me is in a Circle now, and my hope is that the structure, shared accountability, and support in that Circle will help him to get moving—to take more steps and learn from others who are traveling similar paths.

I hope the road ahead takes him, and you, to some wonderful places. 

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Anja’s Story (from the new edition of Working Out Loud)

This story is from the first chapter of Working Out Loud. (Which is now available for pre-order in German too.)

Like other stories in the book, and thousands more in WOL Circles globally, it is about the power of making contributions and connections, earning you access to more possibilities. It’s about self-determination, exploring ways to make more of all you have to offer and realize more of your potential.

I hope you enjoy it, and that you will use Working Out Loud to write your own story.

Click on Anja’s photo to see her LinkedIn profile

Click on Anja’s photo to see her LinkedIn profile

***

Anja earns access to more possibilities

Anja grew up in a picturesque small town of fewer than fifteen thousand people. Upon graduation from the local high school, she applied for an internship at a savings bank about fifteen minutes away. She got the job. 

After four years, Anja knew she wanted more from work but didn’t think she could get very far without a university degree. So she enrolled in a college with an evening program, and for several years she juggled working during the day with going to classes and studying at night. Meanwhile, as it became clear that a career in a local bank wasn’t going to be enough for her, she moved to a large company in a nearby city and got an entry-level job as a clerk in the Purchasing Department. 

When she finally graduated, though, after all those nights and weekends of extra work, she was offered a role as a secretary. It was disappointing. She said, “All that effort to get a degree just to sit there in the end and stick receipts on my boss’s expense report made me more and more frustrated every single day.” Then she paused and slowly repeated that last phrase, as if reliving it: “Every. Single. Day.”

It wasn’t that she thought being a secretary was beneath her or was necessarily a bad job. She just felt she could contribute more. “I wanted a job where I could bring in my passion, where my talents could be seen, and where they would be useful for the company at the same time.” Although her new company had many, many jobs that might be more meaningful or fulfilling, she had no idea how to show she was qualified for them, or to get any extra experience she might need. Although Anja was only in her early twenties, she began to feel stuck.  

Being a secretary is usually a behind-the-scenes kind of job, where few people other than your manager know what you do, how well you do it, and what else you’re capable of. But Anja figured out a way to make herself and her work visible. She had seen that the company was promoting their internal collaboration tools and that a “digital transformation” was part of the corporate strategy. So, she started a blog and called it “How to work digitally as a secretary.”

She began by writing about the tools and techniques she used to be more efficient and effective. The point wasn’t to show off, but to be genuinely helpful. A few people read her first posts, then a few more.

She started to get comments thanking her for the tips she was sharing, and wanting to know more about her approach and how she handled her work. Gradually, her writing began to attract thousands of views, and was shared by colleagues she didn’t know. Her network started to grow. “People started to consider me an expert,” she said. One of the people who took notice of what Anja had to offer was her boss, who offered her a different role.

Anja moved from being an assistant in the Purchasing Department to being a community manager for two online groups in the division. From there she took on the title of “agile coach,” conducting training, coaching individuals, and facilitating workshops. Now she regularly acts as a mentor for teams, departments, and leaders, and she actively promotes digital collaboration and networking throughout the division. Recently, she organized a huge cross-company conference, and shared the stage with two board members. 

“It wasn’t easy,” she said. “But it was worth it. I can now show my talents, and live my passion, in my new job.” Anja no longer feels stuck or invisible. Instead, she has found a way to realize more of her potential, and it feels like a new beginning.

Anja is on the far right, together with board members and other managers from Bosch & Daimler, celebrating the WOL Conference she co-organized.

If someone you know is looking for a job

We first talked about “WOL for job hunters” over breakfast. It was February, and he needed to catch the last flight to Zurich before the US closed its borders.

The experiment we discussed ended this month. Here’s what we learned.

The basic idea

Christoph Lindinger’s company, skillsgarden, helps individuals with their careers and helps companies with innovation, leadership, and culture. He wrote to me about using WOL Circles to assist people finding new roles. That led to our meeting where we agreed on how it would work.

Christoph said he would bring together a diverse group, at least half of whom would have the goal of finding a new role. He would meet with the group along the way and collect feedback.  

Each week, I would send them the new Circle Guides via email and include examples related to their goals. I grew to feel like I was a part of their journey, giving them support and a gentle nudge each Sunday.

Feedback from the participants

After their Circle ended, I met the group for the first time. On the video call was a delicious buffet of accents: Italian, Finnish, Sri Lankan, Welsh, German, Swiss.

I knew the skills they worked on in their Circle would help them access more opportunities. After all, purposefully building your network and shaping your reputation through visible work are fundamental to any job search

What I underestimated was how they would feel.

For those looking for a job, the Circle gave them a sense of psychological safety and connection. The support, shared accountability, and structure of their Circle helped them make progress and feel good while they did it. Just as important, they felt they were more than their goal, more than just a label like “unemployed” or “laid off.” 

As other Circles experienced, they started as strangers and became friends by the end.

Using a Circle to find a job

There are many good courses to improve your interviewing skills, LinkedIn profile, resume, etc.  If you have been laid off, there are outplacement companies like Lee Hecht Harrison that are paid to help you. (One of the Circle members actually worked with them.)

But what do you do when those courses and services end? 

If someone you know is looking for a job, encourage them to join a WOL Circle to complement the traditional job search offerings. You’ll be helping them develop skills and increase their odds while they strengthen their confidence and sense of self-determination.

That’s a wonderful way to support someone looking for the next step in their career.

I’ve felt uncertainty, anxiety, and worse when leaving one job & looking for the next. A WOL Circle can help.

I’ve felt uncertainty, anxiety, and worse when leaving one job & looking for the next. A WOL Circle can help.


How will they know how good you are?

When I first thought I was going to be laid off, I began interviewing for jobs. That was more than ten years ago. Yet I still remember how bad I felt about the process.

At the time, I had no network or online presence, so I relied on recruiters to get me in the door. They matched me to positions that had the same keywords on my resume, even though that was no longer what I wanted to do.

When I met with a prospective employer, all I had to show for my career and capabilities was a two-page work history and my answers to a few interview questions. If they called a reference, I’d have to hope that person had something good to say about me.

“Career roulette” is what it felt like. And the stakes were particularly high. 

Not a game anyone needs to play

Currently, more than 26,000,000 people in the US have filed for unemployment. That’s 73% more jobs that have been lost than in the 2008 financial crisis. 

For the millions looking for a position, how would any employers know how good they are? Or if the job someone used to do is no longer possible, how will they ever be matched to other opportunities that are suited for them?

The answer isn’t (just) a better resume and LinkedIn profile. It’s a combination of actively searching, experimenting, learning, and building relationships. It’s about contributions that shape your reputation and connections that earn you access. In short, it’s Working Out Loud.

Increasing your odds

Recently, I spoke with someone in Switzerland who works with job hunters, and he started to use WOL Circles to help them. In his program, they work on a range of fundamental skills like interviewing and new technologies. The Circles build on that, helping them put those skills into practice and develop their network. For some of them it “changed the way they see the modern world.”

If you or a friend are looking for a job, consider joining a Circle to complement your search efforts. The structure, shared accountability, and support can help you make progress and feel better while you do it. 

In an upcoming version of the Circle Guides, there’s a quote: “Opportunity can’t knock if it doesn’t know where you live.” That’s true now more than ever, and more important too.

How will they know how good you are? How will you find a next step that’s right for you?

How will they know how good you are? How will you find a next step that’s right for you?

A 21st-century skill & the jobs that require it

Recently, I happened to notice “Working Out Loud” in a job description on LinkedIn. Then Mara Tolja, my friend and WOL Coach in New Zealand, sent me another job that included WOL. Then another one. And another one.

“We should maintain a list,” I said. And she created one: workwell.co/WOLjobs

The diversity of roles is striking. From technology companies in Portland and Bucharest to the German train company in Berlin to the Cabinet Government Office in London. One job is for a UN Development Program in Mbabane, Swaziland, a town of 94,000 people.

Five years ago, the well-known author and analyst, Dion Hinchcliffe, recognized that companies would need employees who could work in a more open, connected way, an approach that enables greater collaboration and faster innovation. He presciently referred to Working Out Loud as one of the “essential next-generation digital workplace skills” and later called it “perhaps the most fundamental” of these skills.

Now it looks like companies are recognizing it too. 

If you want to be the author of your own life

The first time I saw the phrase, I thought it was beautiful: “Be the author of your own life.” It seemed so appealing and uplifting, like “Be the CEO of your own career” or “Be the change you want to see in the world.” The prospect of self-determination inherent in the phrase, the power to actively craft your own future, seemed to offer both hope and inspiration.

But the more I reflected on it, the more it seemed like a cruel hoax.

After all, what prepares you to be the author of your own life? Is it the HR survey that tells you what your strengths are? The personality profile that describes your color or element and suggests jobs that are right for you?

Of course that’s not enough. You can’t be an author unless you actually write. And read. A lot. You need to do it every day, day after day, until you develop the skills, habits, and mindset of a writer. It’s your deliberate practice over time - experiments, feedback, connections - that enable you to develop the grit and heart and craft you need to make something great..

The same goes for an intentional life. You must explore, attempt, fail, learn, and adapt over and over and over again. Only through an endless series of small steps will you develop a sense of what feels right for you, broaden your understanding of what’s possible, and expand the perimeter of your potential. 

Crafting a life is not something you say or wish. It’s something you work on every day. Start now.

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Your perfect month

The inspiration to do this exercise came from Moyra Mackie, the first person I ever called “coach.” At the time, I was working at Deutsche Bank, struggling to write drafts of Working Out Loud, and feeling like I was paddling in a leaky canoe - lots of activity but not much progress or direction. 

On one of our phone calls, Moyra suggested that I write down what my “perfect month” might look like in a year or two. That timeframe was far enough away to give me the latitude to do different things, yet close enough that I needed to be practical. My perfect month wasn’t just about sitting on a beach in Okinawa, but about a way to earn a living while living a balanced life.

So I took a piece of paper, wrote down the days of the month, and started to imagine what I would do each day. 

The things I began listing I had considered before. Yet something about mapping those ideas to specific days in the month made them seem more real - and made me ask myself more questions. Yes, I would like to travel, write, do research, etc. But how much? One day a month? Five? Ten? I found myself visualizing my days and weeks. I imagined how it would feel - how I would feel.

I could see this was a good visioning exercise, and I enjoyed doing it. (It’s a nice companion to the “Letter from Your Future Self” in Week 7 of a WOL Circle.) Then I put the piece of paper away, and forgot about it. 

That was a few years ago. I happened to find that piece of paper recently and was struck by how much of it describes my last month, and the month before that. Though my “perfect month” wasn’t meant as an exact prescription or prediction, it captured a direction I wanted to take. It enabled me to see an example of what a more balanced, creative, fulfilling portfolio might look like.

That exercise helped me appreciate how articulating your intention can be extremely powerful. It can help you identify what experiments you might do to see if the direction is a good one for you, and who you might build relationships with to discover more. It can help you make that all-important shift from feeling stuck to taking a step.

When you reflect on your own career and life, where are you heading? What’s your perfect month?

The bridge from where you are to where you want to be

It seemed like something was missing for her. She was working inside one of the world’s largest corporations and, though she liked her job, what she really enjoyed doing was coaching other people. When she told me how she had looked into professional certifications and coaching jobs, her eyes were shining.

Then she paused. “But there are already 200,000 life coaches in Germany,” she said, “and I have a child.” She knew it would be tough to make a living, and was aware the odds were against her. Yet if she didn’t try, she might always wonder “what might have been.” 

What would you do?

The problem with building bridges

For most of my life, I thought of a career as a set of well-planned steps. Like building a bridge, there’s a grand plan, and you need to spend a lot of time and money (training, entry-level jobs, struggles to get customers), before you can reach the other side.

That’s an awfully risky approach - for two reasons. The first is that there’s a huge gap between the idea of doing something for a living and actually doing it every day, and it’s a terrible thing to realize your dream job is nightmarish in reality. Second is that the job you chose to strive for is just one job you happen to know about, and ignores the much wider array of possibilities you never knew existed.

You might build a bridge only to realize you don’t want to go to the other side after all.

More possibilities with less risk

Now more than ever, career planning is an oxymoron.  Instead, a much better approach is to start with only a general direction in mind, and then conduct small experiments that help you learn what a good next step might be. That’s “purposeful discovery.” Your experiments could be as simple as contributions to people related to your goal, or a conversation with someone who’s already doing what you have in mind.

For the woman who wanted to be a life coach, she might start by offering her services for free to colleagues at work, thereby helping people and gaining valuable experience while still getting a paycheck. She could meet with professional life coaches to better understand what being a coach is truly like. She might even try to find all the other life coaches in her company and connect them online so they could all share their experiences.

These kinds of free experiments would help her refine her sense of what she likes and doesn’t like, and expose her to other possibilities she hadn’t considered. Maybe over time she discovers her dream job is not to be independent after all, but to act as an internal coach in her company, or lead a community there, or offer a coaching framework that lets other companies tap into their own internal expertise. Only with experimentation, feedback, and connection will she discover that.

The bridge between where you are and where you want to be isn’t a bridge at all. Rather, it can be more like a leisurely hike through the woods. You have a general direction in mind and take a few steps, mindful of the signs and clues around you, and a path emerges. This approach gives you access to more possibilities with less risk. It may still be strenuous, but you’re much more likely to enjoy the journey.

You are talented enough

As a manager, I used to place people into 9-box grids with axes labeled “potential” and “performance.” It was ludicrous, of course, as we had few if any objective measures of either. But the process required it, and we went about our farcical task with all the seriousness of self-important men. We approached our search for “talent” within our organizations as if we were looking for ripe strawberries. Worse still, we chose to develop only those few we picked.

I wish I had been smart enough and brave enough back then to ask, “Potential for what?” “Performance of what?”

Angela Duckworth, author of Grit, makes the point that it’s not innate talent that matters so much as “passion and perseverance.” She quotes William James, the eminent psychologist in the early 1900s:

“The human individual lives usually far within his limits; he possesses powers of various sorts which he habitually fails to use. He energizes below his maximum, and he behaves below his optimism.”
‘Of course there are limits,’ James acknowledged. ‘The trees don’t grow into the sky.’ But these outer boundaries of where we will, eventually, stop improving are simply irrelevant for the vast majority of us. ‘The plain fact remains that men the world over possess amounts of resource, which only very exceptional individuals push to their extremes of use.’”

Nietzsche viewed our fixation with “talent” as an excuse: “If we think of genius as something magical, we are not obliged to compare ourselves and find ourselves lacking.”

“Do not talk about giftedness, inborn talents! One can name great men of all kinds who were very little gifted. They acquired greatness…They all possessed that seriousness of the efficient workman.”

When I worked in big companies, our ill-conceived search for a talented few led us to largely ignore the potential of the great majority of employees. Now, I know it isn’t some rare, innate trait that’s required to do great work and live a meaningful life. It’s passion and persistence. It’s curiosity and a willingness to experiment. It’s years of small steps, deliberate practice, and resilience in the face of setbacks. 

You are talented enough. Now what? Will you wait to be picked, or will you start the long, serious work to pick yourself? 

When you’re looking for your purpose, “Build your way forward”

Even if you’re fortunate, it’s a common pattern. You begin with a sense that you’re meant to do something purposeful, that you’re special. With the passing of time and with each job, however, that sense of specialness fades. It’s replaced by a nagging disappointment or, worse, resignation. I guess that’s all there is. 

That certainly was my own experience. When I was young, I had high hopes but I also had no idea of what I wanted to do. So I simply reacted to whatever presented itself. As I got older, I relied on my experience in my first jobs to advance and make more money. Doing anything different seemed increasingly impossible. How could I start over?

Recently though, I’ve observed a different pattern. It’s one that gives me hope, and is something anyone can implement on their own. The pattern has three stages: Interest, Practice, and Purpose.

1. Interest

The best description I’ve found of how to explore your interests is in Designing Your Life, based on a course taught by two professors at Stanford. They refer to it as “wayfinding.”

“Wayfinding is the ancient art of figuring out where you are going when you don’t actually know your destination. For wayfinding, you need a compass and you need a direction. Not a map - a direction… Since there’s no one destination in life, you can’t put your goal into your GPS and get the turn-by-turn directions for how to get there. What you can do is pay attention to the clues in front of you and make your best way forward.”

Maybe you have an inkling of what you’re interested in. Maybe you took a test and it pointed you in a direction. Then what? What would you do next, and how might you explore other interests that might be even better for you?

“Try reframing the challenge as an exploration of possibilities (instead of trying to solve your problem in one miraculous leap)…The way forward is to reduce the risk (and the fear) of failure by designing a series of small prototypes to test the waters….one of the principles of design thinking is that you want to ‘fail fast and fail forward’ into your next step.”

The book is filled with many examples of such prototypes, and the simplest and easiest one is a conversation with someone doing something related to your interest or goal. If you’re interested in real estate, talk to people already working in different real estate businesses. If you have a hobby you love, seek out and connect with people who’ve developed that into something more. 

2. Practice

Now comes the part most people miss: deliberate practice. The goal of prototyping and experimenting isn’t to get to some finish line. It’s to get you to the next experiment, to help you explore possibilities while you learn and develop new skills. It’s the combination of doing, interacting, and getting feedback that enables you to advance in the direction you’re interested in. 

For example, I’ve always had an interest in writing, yet for decades I didn’t do anything about it. I started by simply reading more, which sparked my curiosity. My first experiment was to write a blog post on my company’s intranet. I was in my 40s. Then I talked with a journalist who encouraged me and gave me constructive criticism and advice. In the first year, I only wrote 6 posts. I struggled, got more feedback, and learned. I began writing once a month, and later wrote my first public post. Writing became a habit, leading to hundreds of blog posts and a book. The skills I developed along the way - and the relationships I developed as I did it - enabled me to discover a new career in my 50s.

“Deliberate practice” isn’t just for one particular skill, it’s for life.

3. Purpose

Angela Duckworth describes the three phases - interest, practice, and purpose - in her bestselling book, Grit. Her research brought her into contact with thousands of accomplished people and she found few “naturally talented” people. 

“The more common sequence is to start out with a relatively self-oriented interest, then learn self-disciplined practice, and, finally, integrate that work with an other-centered purpose.”

It’s that third stage that is perhaps most surprising to me, and I’m only now starting to understand it. It feels like an awakening of some sort. A psychologist interviewed for Grit described the third stage as when “the larger purpose and meaning of work finally becomes apparent.”

Your next step

The way to design your life is to “build your way forward," using a series of prototypes and interactions to enable you to make it through the three stages. For me, Working Out Loud is what helped me explore my interests, and my WOL Circles have helped me to keep practicing, to continue experimenting and connecting and learning until a purpose emerges.

If you’ve ever felt there is a gap between what you do and something that would be more meaningful, the way to bridge that gap is not with a daring leap but with hundreds or even thousands of small steps. Purpose isn’t something you discover or are born with as much as something that emerges from your passion and perseverance.