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Embracing the Squiggly Career

A squiggly career is a career that isn't defined by climbing the corporate ladder but is fluid and can take many different paths. Here's how to embrace the new and exciting career paths that will characterize the future of work.

Ryan Carruthers

July 11, 2021

The idea that employees climb the corporate ladder and stay with the same company throughout their careers is antiquated. Instead, a new idea is taking its place. To build a successful career in the 21st century - a time of disruption, creativity, innovation, and rapid change - individuals need to embrace the Squiggly Career


What Is A Squiggly Career?

A squiggly career is a career that isn't defined by climbing the corporate ladder but is fluid and can take many different paths. Coined by two career development consultants Sarah Ellis and Helen Tupper, in their 2020 book on the topic, challenge the idea of what progression looks like in a career. They argue that progress in your career isn’t limited to getting a fancier job title or receiving a pay increase. Instead, progress is what you define it as:

  • Having more flexibility in your job to decide if remote work or in-office work is what you prefer.
  • Having more freedom to decide what kind of work you do or projects you take on.
  • Having mentors to guide you and provide advice so you can decide your own career development.

These are just some of the more personalized ideas we can consider when embracing a Squiggly Career. Here’s how Helen Tupper defines a squiggle career:

“We might have expected to have linear, predictable, staircase-like careers, but the reality for a lot of people is that their careers are much more fluid; there’s much more change going on in them.” 

Why Are Squiggly Career On The Rise?

There are several reasons our careers look more fluid than our parents. In their TedTalk on Squiggly Careers, Sarah Ellis explains that she’s had more career changes than her father in half the time. Her experience is common now. 

In 2016 The Bureau of Labor Statistics (BLS) found that the average person will have 12 jobs throughout their career. This fact is why many people refer to millennials are the job-hopping generation.

Painting millennials as fickle and lacking loyalty is a narrow view of why Squiggly Careers are more common nowadays. The real reasons are broader:

  • Technological changes and disruption.
  • Changing jobs is how to get a raise in today’s economy.
  • People are spending, on average, less than five years at a company.

So the reason for Squiggly Careers is partly attributed to changing perceptions about work but also changes to the economy. 


How To Embrace The Squiggly Career?

You’re likely to have a Squiggly Career and that’s a good thing. They offer more opportunity, flexibility, adventure, and options. But with the increase in options, we have to evaluate better what opportunities to say yes to and others to turn down. 

We can’t do everything, so we need to understand our goals and motivations clearly. If we don’t, we risk chasing after the wrong things and ending up feeling stuck or unfulfilled in our careers.

Here’s how to embrace a Squiggly Career:

  1. Know your goals and motivations
  2. Direct your own learning and development
  3. Talk through your goals and ambitions with a mentor
  4. Network continuously 

Let’s go into more detail about each of these. 

Embracing a squiggly careers means knowing your goals and motivations, directing your own learning, having mentors to guide you, and always networking.

Defining Goals And Motivations

Because Squiggly Careers are diverse and can take many different paths, it’s important to know your values, goals, and motivations. Without this clarity, you risk making decisions that affect your career path in the short-term rather than long-term decisions that will ultimately lead you to a fulfilling career. 

Deciding on your goals and what motivates you is the first step in embracing a Squiggly Career. It will require some soul searching and likely a lot of conversations with those close to you. 

John Doerr is an engineer, acclaimed venture capitalist and the chairman of Kleiner Perkins. In this Ted Talk, he breaks down why the secret to success is setting the right goals. Doerr shows us how we can get back on track with "Objectives and Key Results," or OKRs -- a goal-setting system employed by the likes of Google, Intel and Bono to set and execute on audacious goals.

Direct Your Own Learning And Development - What Are You Good At?

Gone are the days of dry, intrusive corporate training programs that aren’t personalized and leave you feeling like they were a big waste of time. Instead, learning and development is moving more into your own hands. For that reason, you’ll have to take a more active approach to what your skills are and what you should develop. 

Many people want to know what their gifts are. The unique talents that set them apart. You’re not alone if the notion of identifying your gifts leaves you stumped. Few people can clearly identify what they were put on this earth to do. 

For that reason, the popular career coach, Marie Forleo, recommends moving away from finding our unique gifts and towards identifying our strengths

Ask yourself these questions to identify your strengths:

  • What comes naturally to you?
  • What can you imagine yourself that gets you really excited?
  • What kinds of projects do you gravitate towards?

Answering these questions is a good first step in finding the areas you thrive in. After you know your strengths, you’ll need mentors who can help you find the opportunities that complement your gifts.

Talk Through Your Goals And Ambitions With A Mentor

Once you know your goals, what motivates you, and your strengths, you’ll need a mentor to keep you grounded. The purpose of a mentor is to help you grow your skills, make better decisions, and gain new perspectives on your life and career. As a mentee, your mentor will leverage their experience to guide you and hold you accountable to grow in your career or life. 

At Together, we’d argue that mentors are essential to career success. Why? Because “79% of Millennials see mentoring as crucial to their career success.” in addition, few executives can look back on their careers and not point out critical mentors who helped them get where they are now. 

To navigate your Squiggly Career, you need a mentor. Organizations should start their own mentorship programs so that everyone can have access to these career-changing relationships. 

But for those who aren’t part of workplace mentoring programs, here’s how you can find a mentor:

  1. Identify individuals who you look up to.
  2. If they’re not in your network, find out if anyone you know is. Ask them to make a connection.
  3. If you know them already, invite them to a "Curiosity Conversation."
  4. Curate questions you want to ask them.
  5. When you do meet them, tell them what you admire about them and that you hope to gain some advice and insight for your career.

These are simple steps, and if you reach out to someone with this request, they’ll most likely be flattered. Out of everyone you could have asked, you chose them. The worst they can say is no.

The conversations you have may answer your specific questions, or they may reveal a different perspective. The point is there is a lot to gain and little to lose. 

Network Continuously To Explore Career Possibilities Rather Than Rigid Career Paths

We’d bet that after having a conversation with a mentor or someone you admire, you’d do it again. You absolutely should consider making it a regular practice to reach out to people - both in and outside your network - to ask them about their careers and draw insight from their experiences. 

In point number 3 above, we encouraged you to invite people to have Curiosity Conversations with you. The successful producer and writer Brian Grazer coined the term. Every two weeks for the last 35 years, he’s invited someone who he’d consider knowledgeable on a subject to have a conversation with him about their expertise. These conversations have transformed his own career and skillsets. 

To learn about the potential that these conversations can have on your career, watch Grazer’s talk at Google.

Supporting Employees Squiggly Careers

Organizations will need to support their employees’ development and growth if they want to retain them. If not, they’ll pursue other opportunities. 

Together’s mentorship software is designed to pair up employees for mentoring relationships. Companies can support their learning and development initiatives, drive inclusion and visibility within their organizations, and connect remote or hybrid employees through our pairing algorithm.

If you’re ready to embrace the Squiggly Careers, employees will have, book a demo to learn more about how mentorship can do just that.

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