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Washed-Up to Wildly Successful: How Reese Witherspoon Pivoted Her Career

Breaking down Reese’s five-step formula for lasting, credible success.

This article was first published in The Startup.

In almost every career path, there’s a crossroads moment.

It might be obvious at once: the moment you are passed up for a promotion or realize you’re up in the next round of lay-offs.

It might be a lot more subtle, like the gradual realization that your work is no longer fulfilling or there’s no way to progress further.

And it doesn’t have to be a matter of sink or swim: it can simply mean drifting aimlessly with the current.

When this point comes, you can either leave things as they are, or take a chance and dive deep into new waters.

I recently encountered this crossroads moment when I decided to leave my job and start a freelance writing business.

More significantly, this is the moment Reese Witherspoon faced when, after a streak of unsuccessful movies, “The New Yorker flung her on the ash heap of has-beens … stars who were no longer stars.”

It’s difficult to build momentum after a stagnant moment like that. And yet, Reese Witherspoon is now one of the most influential people in Hollywood. Not only does she get the roles that were once so hard to come by; she also shines as a leader in the film industry, creating opportunities for women who follow in her footsteps through her production company, Hello Sunshine.

She did this by pivoting her career to amplify her greatest strengths and passions.

Although we can’t all be movie stars, Witherspoon’s formula for success stands out regardless of her career path. Following these steps can transform any washed-up career or business into a wildly successful one.


1 | Notice When Something Isn’t Working Anymore

Looking at Reese Witherspoon’s early career — her starring roles in Election and Legally Blonde, her Best Actress Oscar for Walk the Line — all bets were on a path of super-stardom.

But early accomplishments don’t always guarantee continued success. Complex roles were hard to find, so she settled for what was available — mostly poorly rated rom-coms.

I wasn’t making things I was passionate about. I was just kind of working, you know. And it was really clear that audiences weren’t responding to anything I was putting out there. Reese Witherspoon, 2014 CBS interview

And just like that, things started fizzling out.

When you reach a moment of career stagnancy, it’s easy to set your aspirations aside and settle into the easy routine of things. This is particularly true in an uncertain economic climate.

That said, it’s important to remember that even in the best of times, the rungs of the corporate ladder aren’t equally spaced for every person who climbs it. Likewise, the path to succeeding in business isn’t always linear.

A stubborn pursuit of something that isn’t working — whether that’s a career path you started on a decade earlier, or a business plan that you created for a very different economic climate — is almost guaranteed to fail. Oftentimes, you’ll be the last person to notice that your lack of passion and initiative is killing your projects — and your chances of success.

Sometimes, in order to succeed, it’s necessary to take a detour from the beaten path. By leaving things up to chance you risk doing everything right and never reaching the top.

When something just isn’t working anymore, it might be time to stand back and take a proper look.

View this post on Instagram

A post shared by Reese Witherspoon (@reesewitherspoon) on Mar 24, 2020 at 9:08am PDT


2 | Reimagine Your Job By Finding Your Secret Weapon

A career slump is simply a gap between what you want and what you have. Of course, it’s easier to say that than to figure out a way to actually bridge that gap.

Bringing in a third party to assess the situation can be helpful here. This could be a friend, a trusted colleague, or a mentor: someone who can help you think outside the box and figure out your greatest strengths.

For Reese Witherspoon, this happened to be her husband, who “pointed out what should have been comically obvious to his wife: that she reads more than anyone he had ever known.”

This simple realization made things click. Reese’s longtime love of reading was no longer just a hobby: it was her secret weapon. Instead of searching for the dream roles that were out of reach, she could find them in the pages of books.

With that in mind, she started her own production company and began optioning the rights to the stories she loved. On the side, she established herself as a reading influencer through her book club, which currently has over 1.6 million Instagram followers.

Everybody has a secret weapon in their arsenal.

It’s the special sauce that makes certain businesses stand out from the rest. It’s the brand that exceeds expectations by wearing its values on its sleeve. And it’s the unique perspective that only you can bring to the table.

Your secret weapon might be disguised as a hobby or an interest. It might be the way you sell or interact with your customers or the change you want to make in your industry.

Whatever it might be, finding this unique strength or niche will help you reimagine your job, give you an edge on the competition, and bridge that pesky gap.

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A post shared by Reese Witherspoon (@reesewitherspoon) on Jan 1, 2020 at 10:00am PST


3 | Sometimes, All You Need Is A Strong Beginning

Venturing outside of a career comfort zone is no easy feat.

Whether you’re starting a new business, moving up the ladder or starting a new project in an area where you don’t have much experience, it can be daunting to think of how you’ll be perceived — both by the more experienced players in the game as well as everyone you know.

When Reese Witherspoon invested her own money to start a production company, she had a lot at stake. If her projects failed, it would directly reflect on her ability — not just as an actress, but as a producer and a business owner.

Faced with these challenges, she remained crystal clear on her vision. She knew she was standing up for what she believed in: showcasing strong female stories, which she felt were lacking in the film industry.

She put everything on the line to tell these stories.

To stand her ground, she needed a strong beginning that would propel her to the forefront of Hollywood.

And after the enormous success of her first projects, including Gone Girl, Wild, and Big Little Lies, it was obvious that she had what author Ann Patchett describes as an “ability to spin paper into gold.

A strong beginning, whether that be a killer business idea you’ve been mulling over for years or a marketing campaign with viral potential to kick off a product launch, should be your focus in the initial stages of any venture.

What you do at the beginning of your career transition matters. Done right, it will establish your authority and build solid foundations for the future of your business or your professional reputation. So, start strong.

View this post on Instagram

A post shared by Reese Witherspoon (@reesewitherspoon) on Jul 14, 2019 at 11:04am PDT


4 | Remember What You Stand For

Reese Witherspoon is a great actress, and her talent shines through in the complex roles she has been able to create for herself thanks to her production company.

Sure, a natural talent like Reese Witherspoon’s is valuable enough on its own to warrant sales. But, as time had already proved for the actress, talent isn’t enough to ensure professional longevity.

Talent isn’t what makes her stand out in Hollywood right now.

What truly makes her stand out is her position as a leadership figure for women in film.

Reese Witherspoon’s projects make a lot of money. This isn’t only because they’re excellent in their own right, and tell stories of universal appeal. It’s also because they wear their values proudly, by consistently emphasizing the role of women, both on and off-screen.

Her projects have rattled Hollywood because they prove that it is possible to make lots of money and still operate with ethics at the core. Each film or TV show Witherspoon produces proves that it is possible to fill a movie with all sorts of women regardless of age, race, sexuality, and ability — both on and off-screen.

Her values are not just a gimmick or a selling point. Instead, they ring true throughout all aspects of the business.

This lesson applies across all industries. For continued success, you need to affirm your authority. And in business, this means having crystal clear ethics and values.

A truly successful business is one that operates with a code of conduct. It shines as an example to others not only because of its unique offerings but also because it is worth following and emulating.

Before making a career transition, starting a business, or a new project, ask yourself what it is that you stand for. Think about the changes you could make in your industry that reflect these ethics.

Not only will this make you a credible authority figure, but it will also provide you with the clarity of conscience you’ll need to continue excelling in your field.

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A post shared by Reese Witherspoon (@reesewitherspoon) on Feb 9, 2020 at 9:19pm PST


5 | Collaboration Over Competition

You might remember that Reese Witherspoon’s initial motivation for starting a production company was her desire to find better roles for herself. Some might say this is a selfish motive — and it would be, if Reese didn’t also create opportunities for countless other women in the process.

From fellow female actors, directors, and co-producers, to the authors penning her book club picks, Witherspoon highlights the importance of collaboration over competition across every aspect of her work.

In a recent Vanity Fair interview with Reese, Ann Patchett points out that it was a collaborative effort that made Big Little Lies such a huge success. “When Witherspoon found out that Nicole Kidman’s production company was also interested in the Moriarty novel, she moved to partner instead of outbid.” By joining forces, the show doubled in value — as well as reinforcing Reese’s brand values.

One of the best marketing tools out there is providing genuine help and value to people. It positions you as an upstanding leadership figure and the point of call for your particular specialty.

And besides, choosing to collaborate instead of competing with them is a badass power move. It shows that you’re mature enough to recognize your strengths and weaknesses, and generous enough to offer opportunities to others.

Lifting others up instead of tearing them down — whether that involves your clients, coworkers, or fellow creatives — is a far more respectable long-term strategy.

And trust me — or Reese, at least — making a career or business move with the view to open opportunities to others will not limit your own prospects. It will do the exact opposite and expand your reach beyond your wildest dreams.


No matter what industry or walk of life you’re in, by following these steps — noticing when something isn’t working, finding a secret weapon that pivots your career, starting strong, establishing rock-solid ethics and choosing to join forces with powerful collaborators — you will find yourself on a surefire path to success.

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