Illustration by Liam Oscar Thurston

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Looking for a Career Boost? What Creative Coaches Want You to Know

Illustration by Liam Oscar Thurston
Looking for a Career Boost? What Creative Coaches Want You to Know
Published February 8, 2019 by Emily Ludolph

It’s common for athletes, executives, and opera stars to have performance coaches—people to set goals, benchmarks, tackle potential, and keep them in shape. But coaching has expanded beyond the C-Suite and the playing field to ambitious creatives at all levels of their careers.

Why this expansion? Part of the answer is pragmatic: freelancers and side hustlers now make of 34% of the U.S. economy. These entrepreneurial workers are following trajectories that don’t have built-in career development, pay raises and promotions, or retirement plans; they must create their own career structures. Sans the traditional office environment, an informal network of mentors and service journalism (ahem, you’re welcome) can often be the only sounding board or context to inform that structure.

But it’s not only freelancers who are feeling the pinch of a career without feedback, context, and professional development. During the Great Recession, large companies cut an entire generation of middle management to slash costs. And afterwards? When CEOs saw that workers kept coming in and performing, those managers were never rehired. The dearth of managers could be connected to so many company staffers now feeling adrift at work, just like freelancers, without the typical culture of management and people development from which previous generations benefited. So coaches stepped into the void, working with independent freelancers and self-starters, but also acting as consultants for big companies, serving as a resource for staff and filling in a management gap with feedback, goal-setting, and advice.

Since they’ve seen it all, we asked a few creative career coaches about the most common problems their clients are facing and got some advice on how to cultivate a career when it feels like you’re going it alone.

1. Recognize that tackling career problems may mean tackling problems in your personal life (and vice versa)

For many of us, there are no clear boundaries between our personal and professional lives; pain points in one area affect empowerment in the other. That’s why coaches address both business and personal goals as one.

“People come to me when they want to grow,” says Kristine Steinberg, who started out as an arts psychotherapist before becoming a coach for companies like New Lab, TED, Adidas, and Microsoft. “We work on the future they want to design, the future self they want to live in,” she says.

Since creatives’ future selves aren’t siloed into separate business and personal inboxes, creative coaches often wear many hats: confidante, mentor, and business partner.

2. Take as much care navigating opportunity as navigating hardship.

Contrary to popular belief, coaches are not only called in at times of crisis. In fact, they’re often most useful to those embarking upon exciting opportunities. Their value is that they provide accountability, no matter what the situation.  

“Creatives don’t struggle for ideas,” says Tina Essmaker, who spent a decade in social work before launching a design publication called The Great Discontent, and now coaches both independent and company clients. “They struggle to make them happen and take action.”

Whether you need help navigating a new project idea, choosing between multiple job opportunities, or stretching into a promotion, a coach can be a useful partner, providing perspective at times of paralyzing opportunity. The most powerful support they can offer is tactically breaking down the project into steps, suggesting resources, setting goals, and providing accountability in a vacuum. “It's like having a partner who's invested in you succeeding, but not invested in the project needing to be a certain way,” says Essmaker.

3. Remember that uncertainty is water in the creative industry. The only island is being brave.

Creatives live in an ambiguous world that is constantly iterating and evolving. The creative’s challenge is to sustainably manage that uncertainty.

For those times when everything is great on paper, but you’re feeling overwhelmed, Essmaker prioritizes cultivating bravery over agonizing what the right answer is. “Being able to hang out in that state of ambiguity long enough to know what's next for you [is important],” she says. “If you try to make a decision out of fear or a scarcity mentality, you're probably going to make the wrong one.”

Essmaker acknowledges that we all have good days and bad days. On the good days, the foundational things that fulfill us and that we value are clear. Trust the compass that comes from those good days to see you through the days that you feel rudderless and frightened. Essmaker advocates taking action while in the optimistic zones. “Make decisions when you're having a good day and you have the energy to have insight,” she says. On the days when you’re scared, wait and sleep on it before you make that life-changing choice.

4. Don’t go to Bali. Go find the problem.

Getting unstuck is a prime reason creatives reach out to coaches, but often it takes some detective work to get through the layers to find the root of an issue that can manifest itself in a variety of ways: feeling out of balance, finding work all-consuming, or just not being happy without knowing why. A client may be struggling with how to ask for a raise, but a coaching conversation may reveal that the underlying issue is the client’s sense of self-worth. Or, a client may voice a desire to uproot—quit a job, leave a relationship, and move to a new city.

“It ends up being a surface level symptom to a different problem,” diagnoses Heath Ellis, who prefers the title “expansion guide” and works with clients such as Creative Morning’s Tina Roth Eisenberg.

Sure, uprooting and moving to Bali sounds great. But wherever you go, there you are; the desire to drop everything and start over doesn’t tackle the underlying issues which will no doubt resurface, even in Bali. “When people tend to run into the same issues—if it were a relationship, it would be ‘I keep dating the same girl and it never works’—there’s a subconscious pattern that needs to be healed,” says Ellis.

Coaches work on finding small steps and changes that put their clients in the driver’s seat in a more sustainable way than doing a reboot every few years. “The answer is not uprooting your entire life and career,” says Essmaker. “It's looking at where you are and the changes you want to make where you are.” To do that, do some soul searching to identify the real energy behind your actions or feelings—anything from boredom to aversion to imposter syndrome—and then map that information back to a place where you can make a change. 

5. Own your results.

The common thread in so much coaching, is for people realize how much control they actually have. Most of the time we act unconsciously, responding to deadlines, responsibilities, and a fear of failure or of disappointing others. Ellis works to get creatives to own their results. “If something doesn’t work, it’s not your girlfriend or your boyfriend’s fault. It’s not your company or your boss. It’s something inside of you,” he says. “You’re creating your results. As painful as that can feel if your results suck right now, that’s super empowering,” he says.

Coaches provide the pillars that support a thriving career—feedback, accountability, resources, soul searching, and someone whose ultimate goal is your individual success. As our world of work becomes ever more entrepreneurial, ambitious, and, frankly, overworked, the kind of support they offer is key to preventing burnout and cultivating a thoughtful and empowered career.


To get you started on exercising those conscious career muscles, we asked Kristine Steinberg to share a few of the questions she asks her clients, to act as soul-searching thought starters. Happy homework!

Are you operating at your highest potential?

  • How are you thriving in your career?
  • How are you leveraging your greatest talents and gifts in your work?
  • Are you living to your fullest potential?
  • If so – why?
  • If not – what is getting in your way?
  • What is your future vision of yourself?
  • How can you manifest that vision?
  • What is one thing you can do today to drive yourself to the next level of excellence?

Are you looking to get unstuck?

  • What patterns in your behavior or actions are becoming repetitive and redundant in a negative way?
  • If there was a new behavior or action you could take to break this pattern, what would it be? Can you commit to that?
  • How do you think people perceive you? Is that okay with you or do you want to shift that perception?
  • What is draining your energy?
  • What would give you energy if you had the motivation to pursue it?
  • If you were not stuck, what would be possible?

With a bit of soul searching and a commitment to acknowledging your dreams and insecurities, you can be on your way to a more fulfilling career.



More about Emily Ludolph

Emily Ludolph is a director at West Wing Writers. She has published in The New York Times, The Atlantic, Artsy, Airmail, Eye on Design, JSTOR Daily, Quartz, Narratively, TED Online and Design Observer. 

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