The document features insights from five prominent marketing thought leaders who reflect on their early career misadventures and the lessons learned that helped shape their success. It emphasizes the importance of storytelling, constant reinvention, and the understanding that marketing is a learning experience filled with trial and error. Each contributor shares personal anecdotes that highlight how diverse paths and adapting to change have influenced their professional journeys.

1. Going Way Back With Marketing’s Top Minds
The Early Misadventures and Lessons Learned of Five of Today’s
Leading Marketing Thought Leaders
Starring Robert Rose, Viveka Von Rosen, Mark Schaefer, Ann
Handley, and Jason Falls

2. Contents
Foreword
“Four Steps to Finding the Artistry in Marketing” by Robert Rose
“Coincidentally Coinciding: How Not to Take the Straight and Narrow Path” by Viveka
Von Rosen
“A Marketing Career Today Means Constant Reinvention” by Mark Schaefer
“3 Things I’ve Learned Since I Was 20-something” by Ann Handley
“The Time Lending to the Details Saved My @$$” by Jason Falls
About the Authors

3. Marketing is a Learning Experience
Great marketing has always been about trial and error and knowing when things are
working and when they’re not. This has never been truer than it is now.
Now long ago, the most prominent voices in marketing were fresh out of school, just
starting their careers, and making their own share of mistakes. Between then and
now, what experiences turned them into the thought leaders they are today?
We asked five of these thought leaders to share with us their most transformative job
experiences and what they learned. We hope you enjoy what they shared with us.
As always, fellow marketers, keep experimenting, keep learning, and keep improving!
- Joe Staples, CMO, Workfront

4. Four Steps to Finding the Artistry in
Marketing
By Robert Rose, Chief Strategy Advisor,
Content Marketing Institute

5. It was 1993, and I had my first - and to this day the best - full time job I’ve ever had. I was a
marketing coordinator for Showtime Networks here in Los Angeles. It was truly where I
found my love for the practice and learned some of the the key lessons that would shape
my career.
I came to Los Angeles in 1987 to be a musician and a screenwriter, and after spending 6
years flailing around doing just that, I decided it might be best to find a career that actually
paid money.

6. I would find it, ironically, in the business I loved - but not in the form I originally thought it
would be. There were really four incredible lessons that I’ve learned, since starting out as a
27 year old at Showtime...
1. Storytelling Matters More Than Data.
I learned early on—especially using data—you can have every single fact on your side, but if
you can’t present it in a compelling, inspiring, entertaining way, you will lose to those who
can. Every time.

7. 2. All Great Content Sells - But Know What It Is Selling.
When I was in the TV business, something I learned from the
famous writer Mike Nichols was that there are only three types of
scenes - a fight, a negotiation or a seduction. In each one - the
audience aligns one way or the other with a point of view. This is
something to take forward in creating marketing content. Every
piece of content is selling something - to convince you of
something.

8. 3. Market Where You’re Going - Not Where You Are.
This is one that’s important to the personal, and/or to the new or
nascent brand. This is similar advice to dressing one level better than
the people where you’re going. You want to present yourself as to
where you want to be, rather than where you are.
In other words, if you have desires to be a CMO, present and describe
yourself as a leader, a thoughtful, inspirational manager who thinks
strategically - even if right now you do SEO or email campaigns as your
job.
And, finally, the most important major lesson I learned - which
wouldn’t come for another 23 years, was…

9. 4. Don't confuse the function and the form of the career I desired.
What I wanted was to write, work with multimedia, perform, and tell stories
as a career. It wouldn’t be until more than a decade later that I realized that I
now do exactly what I dreamed of doing. It’s just the form of it is entirely
different than I imagined.
Focus on the function of what you want to do - and be open to all the
different forms that will ultimately present themselves to you as
opportunities.

10. Coincidentally Coinciding: How Not to Take the
Straight and Narrow Path… and Why It’s Ok”
By Viveka Von Rosen
LinkedIn Expert, Author, & Speaker

11. Truth be told, I didn't actually start out to be a marketer. I thought I was going to be a
professor…. until my PhD advisor told me that I would hate the life. After some deep
introspection, (and a look at my other friends who were already miserable PhD's) I
decided she was probably right.
So I decided to go off and fly hang gliders for a while. A lot of fun—but not the best
path to income generation.
After living on the road and in a van for a few years began to get a little old, I
launched into my life as a serial entrepreneur (Coincidentally coinciding with
becoming a marketer).

12. The first business I co-owned (and my first true experience in business
marketing) was a Tack Store—selling equine gear to local young riders.
As a bootstrapping entrepreneur, I had a crash course in Marketing…
and sales and networking and BI and lead gen and biz dev and all the
acronyms.
Then I joined a local education company, Pathfinder, as their marketing
director. After a few really great years, however, I found myself itching
to leave Florida!

13. Lessons learned:
Sometimes turning your hobby or passion into a business kills your
enjoyment of the hobby.
Being able to combine business passions in your work can result in
explosive personal and business growth.
Research your business partners ahead of time!
Never be afraid to jump into the unknown. You can learn skills at any
time, but unique learning experiences are worth their weight in gold!

14. From buggy Florida I moved to beautiful Colorado. However, the
marketing position I thought I was getting—fell through. And I ended
up selling cars. For a long time.
I was soon headhunted by a medical device company, but the co-
owners of the business had a falling out—and I was caught in the
middle.
Lessons learned:
If you are going to move across the country for a job, make sure you
have it first.
If you’re going to work for a family-run business, make sure the family
actually likes each other.

15. Fortunately, I quickly landed a new job as the co-owner and general
manager of a virtual officing company. Once again, I got to explore the
entrepreneurial and marketing side of things.
Also, I sucked at managing.
Lessons learned:
Know what you are good at. Trying to force yourself into a skill set that
you suck at doesn't help anyone. Including yourself.
Some people just aren’t meant to work for other people.

16. Around this time, I discovered LinkedIn. It was the early days and I saw
an opportunity. With a leap of faith (and a certain amount of luck) I was
able to quit my day job and embark upon the career I have now.
That was 10 years ago. Since then I have learned an enormous amount
about marketing and business! I've learned how to run a business. I've
learned all about social media marketing and social selling. I've learned
how to create and build a speaking career. And I've learned how to
manage clients.
My path to my marketing career was not a straight one. Nonetheless, I
have been granted an enormously rich education through real life
experience—and I think I have come out the other end better for it.

17. A Marketing Career Today Means Constant
Reinvention
By Mark Schaefer
Consultant, Educator, and Author of The Content
Code

18. As a young man, I couldn't have known what was ahead of me but there
has certainly been a pattern to my career. Here’s a little story to illustrate
it...
In the mid-1990s, companies were finally starting to learn that there was a
business role for the Internet. I was a young marketer and I knew I needed
to be part of this next wave. So I asked my boss if I could get an AOL dial-up
account for our marketing department and put it on my expense account.
He agreed, and I became the first person in my company on the Internet!

19. At each stage of my career I had a sense of where the world was going and
where I needed to be. And I acted on it.
As it turned out, about every five years I reinvented myself. I started in PR
and moved to developmental sales, then enterprise sales, and eventually
global marketing, eCommerce, and digital marketing.
I didn't start my latest career as a teacher, consultant, speaker, and author
until I was almost 50!
Why am I always on the move? Because I know life is chasing me. If I didn't
re-invent myself periodically, I would lose out to people who did.

20. I once met an elderly man who had been in the insurance
business in Florida. A lot of the regulations had changed
and, to keep his license, he would have had to submit to a
battery of state tests. He decided that he could no longer
keep up, and he did not take the tests. Now he was
miserable and lost because he was disconnected from the
career he loved.
I won’t let that happen to me.
The scary thing is, it’s time to reinvent myself again. I’m
getting the five-year itch, and that is a good thing.

21. Look around you. Where do you see marketing
going? Where do you need to be?
Big Data.
Virtual reality.
Analytics.
3D printing.
Drone deliveries.
Driverless cars.
Mobile.
Enterprise work management.
Marketing automation.
All of these will have a profound impact on your
marketing job, and your work life.

22. As a young man I had a SENSE that I needed to change, and
now I KNOW I do.
You do, too. Get ahead of the curve. Be ready when your
company needs to you adapt to the latest trend.
Ready to get started on your reinvention?

23. 3 Things I’ve Learned Since I Was 20-
Something
By Ann Handley
Author and Chief Content Officer
MarketingProfs

24. 1. Paths aren’t linear.
When I was a child, I didn’t lie in my twin-sized bed and
wish, “Someday, I’m going to be the world’s first Chief
Content Officer!”
I got here through a series of left, rights, roundabouts,
barrel rolls, and triple toe axels.
Some of those felt like the wrong turn or an awkward
move at the time. But none ultimately were – even the
ones that were missteps – because even a wrong move
teaches you something. Or maybe, especially a wrong
move.

25. I quit jobs with steady paychecks to freelance full-time.
I took gigs I wasn’t really into just for the money.
I’ve worked for free because I felt in my gut that it would ultimately pay off.
Are you thinking, “Oh sure – I was an intern, too”?
I wasn’t an intern. I was a grown-up who’d already built and sold a company a
few years prior. It was MarketingProfs I worked for, for free. And it did pay off.
(And still is.)

26. 2. Your rich thing is everything.
When I was 8, I wrote in my diary, “I want to be a writter.” (Even
then, I knew I’d always need a copyeditor to help with the spelling.)
Writing is my thing. But my bigger, richer thing is clear, compelling
communication, period.
Clear communication. Simple but not simplistic. Respect for the
recipient. Regarding an audience as a privilege.

27. All that is the through-line throughout my entire career as a
journalist, editor, marketer, author, and speaker.
I could argue that in high school it also helped me become the
assistant shift manager when I worked the window at Jack in the
Box. My “Drive up, please!” was hella direct, crisp, and clear.
(Kidding.) (Kind of.)
Commit to your rich thing, whatever that might be. Lean into it.
Learn it. Rub it all over your body and wallow in it, neck deep.
Get obsessed with it. Go all in or no in.
But realize…

28. 3. You’re never 100% competent.
The more you master, the more you realize you don’t know.
That sounds a little depressing, doesn’t it?
As in: What’s the point of all that neck-deep wallowing when
there’s so many more pools in the world in which you have
yet to wallow?
Maybe. Or consider the fun of discovering all those pools in
need of your wallowing body. Consider the challenge of
giving it your all.

29. The truth is this: To stand still is to fall behind. --
Mark Twain
Disheartening? Or motivating? I’d say the latter.

30. The Time Tending to the Details Saved My @$$
By Jason Falls
Keynote Speaker, Consultant & Author
Social Marketing & Intelligence

31. Having grown up in the marketing world as a public relations
guy in a niche industry (college athletics), I didn't gain
exposure to the mainstream marketing and advertising world
until my mid-30s. But being smart enough to know what I
didn't know, I wrote everything down, made sure I had
paperwork on everything, client's signatures and such. On
the first true advertising account I handled, this turned out to
be an example of being wise beyond my years.

32. The client was a company with an industrial product who hired my agency
to help differentiate its message from the stale, predictable, boring
standards in their industry. We went through 2-3 rounds of creative to
come up with a campaign that really stood out and executed the first few
advertisements in a couple of trade publications.
The day after the trade pubs came out, the "chief of staff" to the CEO
(which should have been a warning sign of unnecessary pretentiousness)
called and fired us.

33. Upon inquiring about the reasons, I was told that the ad campaign as an
embarrassment, brought unnecessary negative attention to the company and
that we were not given authorization to execute the campaign. The client was
refusing to pay for about $50,000 in work.
But I forwarded the signed run flights to the client, showing them where the
CEO himself had approved the creative and the ad buys and we were
protected. Ironically, I don't consider myself to be a detail guy. But tending to
them in that instance saved the agency and my ass.

34. Where will your marketing career take you?
The path to marketing success is often dotted with tangents, misfires, and
failures. But that path always comes back to tenacity, an ability to learn
and adapt, and a healthy sense of humor. It always comes back to
discovering those timeless principles getting rid of the things that hold
you back, building relationships with the people you work with, and
seeing where you need to be next.

35. About the Authors
Ann Handley
Ann is a Wall Street Journal best-selling author, keynote speaker, and the
world’s first Chief Content Officer. She has been cited in Forbes as the most
influential woman in Social Media and recognized by ForbesWoman as one of
the top 20 women bloggers.

36. Jason Falls
Jason is a digital strategist whose work has touched a number of large brands,
including Maker’s Mark, AT&T, Cafepress and Humana, to name a few. He has co-
authored two books and is a professional public speaker. Jason focuses on digital
marketing with a specific niche expertise around social media and content
marketing.
Mark Schaefer
Mark is a globally-recognized blogger, speaker, educator, business consultant, and
author who grows blogs at {grow}—one of the top marketing blogs in the world.
He specializes in social media training and clients include both startups and global
brands such as IBM, AT&T, Johnson & Johnson, Adidas, and the UK government.

37. Robert Rose
Robert is an author, a speaker, a consultant, and the Chief Strategy Advisor
for the Content Marketing Institute and a senior contributing consultant for
Digital Clarity Group. He innovates creative and technical strategies for a
wide variety of clientele, such as AT&T, The Bill & Melinda Gates Foundation,
Petco, Caterpillar, ADP, Fairchild Semiconductor, and KPMG.
Viveka Von Rosen
Viveka is known internationally as the “LinkedIn Expert” and speaks to
businesspeople on the benefits of marketing with social media. The author
of LinkedIn Marketing: An Hour a Day, she is also the host of the biggest
LinkedIn chat on Twitter, with over 32,000 followers and a network of over
42 million people on LinkedIn, and 82,000+ followers on Twitter.

38. Learn Faster, Execute Faster
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