Career Transitions, Next Chapters, and Personal Differentiation Strategy
Find out what makes you special and how to market yourself
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In the spring of 2022, I was burned out and knew I needed to make a change. I decided to leave my full-time job at the company I co-founded, even though I didn’t know what I wanted to do next. All I knew was that I wouldn’t be able to discover my next adventure without leaving the current one.
I had also just turned fifty, and my youngest kids were preparing to leave for university in the fall. It was not a mid-life crisis, but it was definitely a lot of big pieces of my identity shifting at the exact same time.
I went into a phase of transition and it was really valuable. I read a lot of books. I did a lot of thinking and writing. I talked with a lot of people. And, even though it took longer than I expected, I’ve emerged on the other side with a lot that I’m excited about in my life.
Having been through this process myself, I find it a real privilege to be invited into a meaty conversation with someone about their career transition or career development. Lately, due to layoffs or life changes, I’ve had a lot of these conversations.
As a way to close out the year here in the Creativity Business newsletter, I want to share some of the big topics, books, and ideas that come up regularly in these conversations. I know a lot of us take stock of our year and our careers around now, and these are all things that helped me immensely.
One big caveat before we dig in: this is written for people who are contemplating a big change or transition. This is not going to be as helpful if you’re just looking for a new job that is similar to your previous job or staying in the same profession.
Book #1: Transitions
There are a number of great books I’m going to recommend, but the first one is a timeless classic from William Bridges called Transitions. The biggest takeaway for me from this book is that we are conditioned to think about everything as:
Beginning → Middle → Ending
However, transitions are the reverse of this. The process of a successful transition is:
Ending→ Middle → New Beginning
A key insight is that when we enter into a life transition, we have an urge to jump from the fresh Ending straight into a New Beginning. The Middle is an uncomfortable void. We don’t like emptiness and uncertainty, so we put pressure on ourselves to get out of the Middle as quickly as possible.
However, if circumstances allow for it, we should instead embrace the discomfort of this liminal state because that is where fresh perspectives and ideas are generated. Embracing the Middle instead of rushing through it will help prevent us from jumping back into the same thing we have always done and will open us up to new opportunities we might not have considered without spending time in the void.
So what do you do while you’re in the awkward void of the Middle?
Who Are You?
It’s important to know what you want before you start looking for new adventures and opportunities. A vital part of knowing what you want is acknowledging who you actually are and what makes you special. These questions seem simple, but I’ve found that thoughtfully answering them really helped me find my next chapter.
Who are you?
What are your values?
What are you passionate about?
What are you curious about?
What are you really good at? Where are you exceptional?
Where do you have unique or unusual expertise and/or experience?
When/where/why do you enter into ‘flow’ states and lose sense of time because you’re deeply engaged?
What makes you WEIRD?
These questions help identify not only what you’re interested in, but what you’re good at and what is authentically you. (You might consider getting a DISC, Myers Briggs, or Strengths Finder profile done if you haven’t before to find out more about your unique traits.) Keeping these answers top of mind will help you from jumping into something that isn’t aligned with who you really are.
What Do You Need?
Another factor to consider is the set of environments you thrive in and the ones you don’t:
Are you happy with the profession you’re in, doing the type of work you’re doing? Or are you looking to make a significant change into a new area entirely?
Do you like working in large teams, small teams, or on your own?
Can you picture yourself in a large company, a small-to-medium-sized business, or working on your own?
How much social interaction do you need in your work life? Would you want to be in a physical office collaborating with others? Working in a hybrid or remote team environment? Or working solo with clients from your home or a co-working space?
You might also have some mandatory requirements or constraints in your next chapter:
Do you have any financial considerations or minimum annual revenue/income requirements?
Are you open to moving to other cities?
How much or how little do you want to work? Full-time? Part-time? Or a set amount of hours of your choosing?
What else is important in your life that needs to be considered? In the pie chart of how you spend your finite amount of time, what are the other pie pieces and how big are they?
Thinking deeply about these questions will help you choose environments that play to your needs and strengths, and can help you rule out options that won’t move you in the right direction.
Book #2: Four Thousand Weeks
As I recently wrote, Four Thousand Weeks by Oliver Burkeman is the book that I have recommended more than any other in the last several years. Why? It fundamentally changed my perspective on what is and isn’t important in my life.
Four thousand weeks is roughly how long the average person is alive. Burkeman makes the case that it is paradoxically liberating to embrace that we are finite humans with finite time and finite possibilities. Once we realize that we can’t do everything we want in our lives, that we’re not going to be here forever, and that we’re not guaranteed anything beyond today, it frees us up to consider what the most meaningful and purposeful uses of our finite time actually are.
There is a strong case made for not putting important hopes and dreams on hold for “someday” when everything is finally done, our problems have all been solved, and the perfect window arrives… because that time will never come. There will always be more to do. There will always be more problems that arise. But there may not always be more time to do the things you really want to do before your short time is up.
While this may sound a bit depressing, it’s invigorating to consider these limitations as you are pondering your next chapter and sitting in the discomfort of the liminal state that is the Middle.
Are there things that you are truly and deeply going to regret if you don’t ever get a chance to do them?
Book #3: From Strength to Strength
If you’re over forty and in a career transition, I’d also recommend reading Arthur C. Brooks’, From Strength to Strength. The big idea that stood out for me with this book is that we have two different intelligence curves in our lives and it’s important to know which curve you’re on when you’re choosing a new adventure.
When we’re younger, we thrive by embracing Fluid Intelligence, which is our ability to soak up loads of information like a sponge, solve hard problems, be entrepreneurial and innovative, etc. Regrettably, our Fluid Intelligence starts to fade in our forties, which means that it is risky to base mid-life career decisions on the skills and attributes that made us successful when we were younger.
The good news is that there is a second curve, called Crystallized Intelligence, and it begins growing at the same time that our Fluid Intelligence is diminishing. Crystallized Intelligence is our ability to see the big picture, synthesize complex ideas, and share our wisdom with others. It keeps growing into our eighties, which is why we should embrace it as we enter middle age and beyond. According to Brooks, this is why some of the best professors in the world are older and why so many people turn to consulting, coaching, and teaching later in their careers.
If you’re in the age range when your Fluid Intelligence might be ebbing, it would be valuable to consider how you might lean into ideas and opportunities that embrace Crystallized Intelligence.
Standing Out vs Fitting In
Let’s assume you’ve spent a lot of time in the void and now have some insights about who you are, what you want, and what you need. Now it’s time to figure out how to tell your unique story and stand out from everyone else. (It’s time to market yourself!)
In today’s job market, AI is screening resumes at scale and job-seekers are using AI to craft resumes to ensure they are optimized to be scanned and read by AI. To me, this is worrisome for a number of reasons, but mostly because it sounds like the result will be resumes that end up blending in with each other.
If we’ve done the work on figuring out who we are and what makes us special, it would seem like a shame to have it stripped away into something conventional and generic to appease the AI screening overlords. So I’m a fan of doubling down on being unique.
This may not be the right approach for everyone, but for me, it has been important and valuable to make myself as differentiated as possible. My dream outcome is to end up as the ONLY person on the planet doing what I’m doing, but still creating a lot of unique value. (Another book recommendation! I was happy to find this strategy validated in The Element, by Sir Ken Robinson)
When I was in the media and applying for a new job, I would almost always get asked why they should choose me for the gig. The answer that got me a lot of jobs was this: “If you give everyone applying for this job the same assignment, mine will be the one that is different than everyone else’s and mine will be the only one you remember a month from now.”
If each of us can find a version of this story about why we are different and what makes us special, it would be more valuable than an AI-optimized resume. So how do you figure out how to present yourself as one-of-a-kind?
Unusual Combinations
Unusual combinations stand out precisely because they are unusual. They break patterns. They are memorable. (Read more about unusual combinations here). Look at the list of things that you’ve identified earlier about what makes you weird, the mix of things where you’re exceptional, where you enter flow states, and what you’re passionate and curious about. Now, start generating unusual combinations of those elements. You might quickly find that you have a fantastic differentiation strategy sitting in plain sight. (Another book recommendation! There are some great exercises for doing this sort of exploration in the book Designing Your Life by Bill Burnett and Dave Evans.)
I’ve had a few of these unusual combinations work for me in the past. When I started Pacific Content, my unusual combination was “Podcasting + Media Executive + Marketing.” That led directly to the first company exclusively focused on making podcasts with brands.
After I left Pacific Content and went through this process again, I emerged with another unusual combination: “Content Strategy + Attention Strategy + Marketing.” I can’t be sure, but I might be the only person with a LinkedIn title of “Attention Strategist.” That makes me weird and easy to differentiate when it comes to my point of view on content and marketing.
(One of my favourite examples of someone who has doubled down on what makes them unique and special is Nardwuar the Human Serviette, who you can read about in detail here.)
What are your unusual combinations? What could make you unique and eliminate the vast majority of your competition?
Share Your Ideas Generously
Once you land on your personal differentiation strategy, how do people find out that you exist?
One option is to apply for jobs with resumes and cover letter. However, as I mentioned above, the AI-ification of job applications fills me with dread about having to make your resume the same as every other resume out there.
Another option is to find a way to let the world find out about you and to instead have jobs and gigs show up on your doorstep. How do you do this?
The answer that has worked over and over again for me is to put out content that shares my passions and thinking in public. I did it with the brilliant Dan Misener at Pacific Content and it changed the fortunes of our company. We wrote a blog post and newsletter every week and we shared everything we knew about podcasting for brands. And suddenly, brands started showing up in our inbox because they were reading our posts.
Whether it’s a newsletter, a blog, a podcast, videos, or even posting your thinking generously on LinkedIn, sharing your unique expertise freely with others lets everyone else know who you are and what makes you special.
The newsletter you are reading right now is proof that I continue to see loads of value in doing this on an ongoing basis. This past year, I doubled down on this strategy by writing a book about how to earn attention!
Bypass the Gatekeepers and Bet on Yourself
This can be a scarier option, but it can also be the most rewarding. There is often a fear of betting on ourselves and a desire (or a need) for the security of having someone choose us to fill an existing job opening.
If your circumstances permit it, you also find yourself with an unusual combination of value, and you’re comfortable sharing the unusual expertise publicly… you might want to consider going for it on your own and betting on yourself.
When you’re truly unique, you might not be a great fit inside a corporation that wants to put you in a tightly defined role. You might find that you have to hide or subvert important parts of yourself in order to get a “gatekeeper” to choose you. In the media, there are still a lot of people who feel pressure to have a job with a traditional media company, for example, even though many of those traditional media companies aren’t going to let them do the work that they really want to do and often don’t understand or embrace the way digital audiences behave.
It requires bravery and confidence, but sometimes the best option is to bypass the gatekeepers and bet on yourself. If you’re interested in learning more about this route, I’d highly recommend one last book, Company of One by Paul Jarvis.
Warning: It’s Uncomfortable
When I went through this transition process, it was HARD. And it was uncomfortable. I had false starts. My patience was tested being in the void of the Middle. I sometimes wondered if I would ever have my “aha!” moment about what my next chapter would be. And, TBH, I got lonely sitting alone at home for too long. So steel yourself that it’s not necessarily going to be easy or quick. But, speaking from experience and with the benefit of hindsight, if you want to make a big change, the hard work and the discomfort are worth it.
If you’re going through a life or career transition, or taking stock of your life at the end of the year, I hope you find these ideas and books as valuable as I did in the last couple of years.
If you’ve gone through this journey or are in the middle of it, what other books or resources would you recommend? Let me know in the comments.
Earn It Updates
I was shocked and extremely pleasantly surprised to find out that Earn It is one of forty books chosen for the longlist of The Porchlight Business Book of the Year. There are so many amazing books and authors on this list, from Seth Godin’s This Is Strategy to Cal Newport’s Slow Productivity and from Charles Duhigg’s Supercommunicators to Lorraine Besser’s The Art of the Interesting. Check out the full longlist here.
Thanks to the amazing and generous Brittany Hodak for choosing Earn It as her favorite read of 2024. Brittany has a fantastic book of her own that shares so many of my own values about the importance of magical customer experiences–you can check out Creating Super Fans here.
Liane Davey, a terrific author, speaker, and consultant, has a wonderful annual tradition called “NOvember,” which celebrates thirty days of saying “NO” to very specific things in the world. I was very happy to contribute a NO this past week, but you should check out the whole month of NOvember posts on Liane’s LinkedIn page.
If you’re in or around Copenhagen, I’m going to be talking about Attention Strategy at Clever Content on January 9th.
If your organization could benefit from a content strategy workshop or a talk about how to thrive in the Attention Economy, just reply back to this email, or reach out at steve.pratt@creativity-business.com.
What’s Earned My Attention Recently
Cohost and Quill asked a lot of podcasters for their predictions and advice for 2025 and the result is a ton of smart and insightful thoughts about the year ahead. My advice is eerily similar to the advice for career transitions!
I know this quote is not about marketing or the media, but it certainly feels relevant to me through that lens!
"Perhaps the greatest impediment to human creativity is the natural decay that sets in over time in any kind of medium or profession. In the sciences or in business, a certain way of thinking or acting that once had success quickly becomes a paradigm, an established procedure."
Robert Greene, The Daily LawsShane Parrish is writing more about attention these days in his excellent Farnam Street newsletter. From this past week’s edition:
“You have just six seconds to capture someone’s attention — but if you interest them, you earn another twenty to thirty seconds.
Practically, this means you have about thirteen words to hook them and another thirty to forty to deliver your most compelling information.
If your email exceeds 100 words, allocate your editing time wisely: dedicate 40% to perfecting the first sentence, 40% to refining the next 2-3 sentences, and just 20% to polishing the remainder.”The Extraordinary Cost of Dull Advertising. Love this piece from Brad Cunha in the Brand Storytelling newsletter!
Why the Mainstream Media has Already Lost - a very insightful article about the state of traditional media, influencers, and the future of journalism from Helen Lewis at The Atlantic.
Thanks to the team at Storythings for sharing this guide for How to Find a Gift (They’ll Actually Love). I believe that the qualities of a great gift also apply to great content, so I loved reading this.
Thank you so much for spending some of your precious time and attention with me in 2024. And thanks to all of you who have supported Earn It in so many ways this past year–i’m extremely grateful to all of you. It’s a real privilege to be welcomed into your inbox every couple of weeks, and I don’t take it for granted.
I hope this edition has been useful if you’re going through a career transition, thinking about a change, or wanting to stand out from the crowd of job-seekers.
Happy holidays and see you in 2025!
Steve
Thanks Steve, what a great newsletter! Sharing with some other folks!
Amazing newsletter!