Pivots — the art of reinventing ourselves.
Pivoting our career has a lot in common with a startup pivot than we might think.
For startups, a pivot isn’t a sign of failure. It’s a strategic shift, a new direction. Pivots can be a powerful way to adapt, transform, and thrive in an ever-changing world. But when it comes to our career pivots, they are not always easy to navigate. We are consumed by fear, anxiety, and doom.
Having worked with startups that have had significant pivots and pivoted in my own career, I’m sharing what I have learned in the hope that it might be helpful to you.
How to know you’re ready for a pivot
Most people tend to ignore the signals for a pivot because it’s scary. We’d rather fail with our feet on solid ground than sprint blindly off a cliff, uncertain of what we’ll meet when we land. But sometimes, it’s necessary to take that leap, and here are a few signals that our career needs a pivot:
Stagnation: Signs of stagnation in our career show up in many ways. We might not be learning or growing in our work. We may feel stuck in our role. We have to push ourselves to do things we used to do with a great deal of vigor and joy. Our Monday blues are epic.
Disconnection: We’ve lost passion or alignment with our original vision for our career. Our work may no longer reflect our personal values, or what used to excite us and move us to act no longer has that kind of power over us.
Market Shifts: The industry could be moving in a different direction. We may find that our skills are becoming obsolete or that we must learn new skills to keep up. What was working before is no longer working.
Gut Feeling: Sometimes, it’s simply an inner voice nagging us, telling us we are on the wrong path. If you have to routinely push yourself rather than be pulled to do your work, something is off. Don’t ignore your intuition. It’s just another form of data.
Hypothesis-based approach
With startups, pivots are not random. They are based on data. If you are paying attention, there are clear signals that tell you that things are not working.
In 2015, when I noticed the signals that I was ready for a pivot (stagnation, disconnection, gut feeling), my first response was a sense of dread.
Why give up a full-time job with benefits to chase some vague idea of self-employment and a dream of becoming a writer? How do I know this will even work? Is it worth the risk?
To calm down my anxious voices, I made a list of observations (data, really):
Every startup I worked for had the same problem—marketing was a hot mess. It didn’t matter which stage.
Most founders came from a technical or product background and did not understand marketing, often simply thinking about it as “lead generation or growth.”
Most founders, especially first-time founders, did not understand how to hire a marketing leader. The VP of marketing role became a revolving door for candidates who were a poor fit.
I knew I was passionate about working with founders to help them get marketing right. I also wanted to write a book, a collection of short stories. A full-time leadership job did not give me the space and time to write. I needed flexibility.
Having made these observations, I decided to run some experiments. Before running an experiment, I needed a good hypothesis that I could prove/disprove with data.
writes about running “good” experiments, and this sentence from his newsletter struck a cord:Good experiments are expressly designed for learning in an uncertain situation and for sneaking past an uncertainty-averse organization.
Or an uncertainty-averse individual. 😉
This was my hypothesis:
If good marketing is the difference between great products succeeding or failing, by working with first-time founders as their first or interim marketer leader, I can help them better understand the function, establish a strong marketing foundation, and help them hire the right marketer.
This substantially reduced my anxiety. I was just running experiments! I wasn’t pivoting yet. Once I have some data, I can act on that.
Run experiments and prioritize
Running good experiments is not as easy as it looks. If you are interested in learning about how to run good experiments, this post is worth a read. The good experiment.
A few pointers when running experiments:
Keep the experiment defined, discrete, and small.
The results of the experiment must be actionable. You must be able to move forward.
It’s not about getting a “yes” or a “green signal” or a “win.” Even if your hypothesis is disproven, that’s super useful learning. It allows you to formulate the next hypothesis.
To prove or disprove my career hypothesis mentioned above, I ran experiments to answer the following questions:
What’s the right stage of startup to work with? Early stage, growth stage, scaling stage?
Consumer or B2B or B2B2C?
If B2B, product-led growth or enterprise?
Should they have a marketing team or not?
How do I know it’s a good fit for me?
Once you’ve made a list of experiments you want to run, ask yourself which experiments can yield the most learning. Prioritize them because you won’t be able to run them all.
My first two years as a solopreneur were all just experimentation. I worked with consumer startups. I worked with B2B startups. Some had teams, and others did not. After every startup engagement, I did a postmortem. What worked? What didn’t and why? This helped me zero in on the right target startups, refine my methodology/approach, and determine pricing.
Set clear, timebound milestones
I wanted to avoid the risk of running experiments for four or five years and learning that solopreneurship doesn’t work for me or that I cannot write stories. Then I’ve wasted a lot of time and won’t have much to show for those years when I return to finding a full-time job.
When I started, I gave myself a one month deadline to land a client. If I didn’t find a startup client within a month, I would find a full-time job. This gave me a very clear deadline, and because I really, really did not want a full-time job, I was determined to find that client.
Once I had a client, my only goal was to get a strong reference. As a marketer, I knew word of mouth matters.
When it came to writing short stories, I was starting from ground zero. I had no knowledge of the craft. I had no experience writing fiction. I gave myself clear, short milestones—take a craft class, read n-number of stories to unpack craft elements, join a writing group, etc., so I could measure progress in this new area.
Measure success differently
We cannot apply the same yardstick we’ve used for our current career to our new one. Success may not be about getting promoted or making more money.
Success could be learning new things. Having flexibility in our life to pursue passion projects. Spending more quality time with our family and children.
With social media, it’s easy to fall into the trap of comparing our new path to our old path. To compare our new selves with old peers who may not have changed careers or pivoted.
In the early days, I had to constantly remind myself why I pivoted. I had to constantly reiterate my priorities—independence, time to work on my book, and quality of life.
Having a daily reminder—a postcard pinned to our office wall, a talisman, a quote—to remind us why this is important to us helps us stay on the path.
Commit to the pivot
This part was the hardest for me. Even after I found fit, I kept second-guessing myself. Was I on the right path? Every time there was a gap in work projects, I’d panic. I’d question the entire enterprise.
While some of this was normal, having this knee-jerk reaction every time I couldn’t see around the corner was unproductive. When I was writing fiction, I worried that I wasn’t working; when I was working, I worried that I wasn’t writing enough.
I learned to counter this by adding some predictability to my life. Now, I get up early in the morning to write. This habit took some time to form, but it is now firmly established in my daily routine. Working out every day, making outreach a part of my daily work routine, and even writing this newsletter on a regular cadence helps. Schedules and routines brought structure and discipline into my life. It also helped reduce anxiety.
Building our support network
Whether we are taking a small pivot, like moving from one role to another, or making a big change to try something entirely new, we need advisors, guides, mentors, and peers. People who can help clarify things to us when we are confused, people we can lean on when we are scared or worried, and people who can introduce us to subject matter experts who can help us learn. Trust me, you are going to need them!
When I started as an interim CMO, there was only one other person who was doing something like this. The terms interim or fractional CMOs, CFOs, or CPOs were not common vernacular. She gave me some great advice on how to get started. I reached out to other business leaders and venture capitalists to get their perspectives on my offerings.
I don’t have a vast network. Building a vast network with millions of followers was never my goal. Instead, I focused on meaningful, high-quality connections. When it came to writing stories, I literally knew no one in the literary world. Over the years, I’ve built my community by attending writing classes, conferences, and workshops. Writing is a lonely enterprise, and I honestly cannot imagine where I would be without my writing mentors, advisors, and fellow writers.
Have you taken pivots in your career? What did you learn? Please share your experience in the comments so we can all learn from you!