INTRODUCING

Ashley’s Vivid Vision

It’s March 2026 and Ashley Jablow is 45 years old. The first half of her 40s had been filled with growth, love, good health, memories and fun. When she turned 40, Ashley had felt excited anticipation at the thought of a new decade, but admittedly a little overwhelmed about what lay ahead. Always eager to set an intention and define her purpose, Ashley set out – along with her husband and life partner Dan – to define her vision for the first five years of her 40s.

Today that vision – and so much more – has come true.

Today, Ashley is a successful coach and facilitator, a published author, and in-demand motivational speaker who teaches people how to design a life they love. Her work is infused with creativity and color, new thinking and old wisdom, and innovation and design frameworks that she’s adapted to make relevant for mainstream audiences. She is regularly sought out as a keynote speaker and has been featured on the TODAY show and in Oprah Magazine for her down-to-earth, authentic and inspiring approach for everyone who wants to create a life they love.

It all started when Ashley fully committed to seeing herself as an artist who creates meaning through her work. She finally stopped seeing her “art project” (as she demurely called it when she first began it) as simply that, and instead chose to fully own her identity as an artist. Once she was able to marry her unique approach to life design with her understated, simple and beautiful artwork, her work and her impact took off.

As her #100DaysofDesigningMyLife project came to a close, a publisher approached her to transform her art into a coffee table book – but Ashley had other ideas. Knowing these prompts had the potential to spark introspection and action, Ashley proposed the idea of pairing 100 daily prompts with short activities that could be compiled together into a workbook. “It’s like a cookbook,” Ashley said, “only these recipes bring together the right ingredients to design your life.”

The publisher paid her a $50,000 advance to refine her artwork and design the companion activities. To celebrate, Ashley booked an all-expenses-paid 2 week trip to Italy for her and her mom Janice. They set up at a local villa with a private chef and a car service who’d take them into town for pasta-making classes, outdoor painting, and wine tasting. They belatedly celebrated Janice’s 70th birthday and talked, laughed and made lifelong memories.

Ashley’s first book was published in mid 2022, and soon audiences all over the world were buying Ashley’s workbook: for themselves, for recent grads, for anyone in a career transition.

As momentum around her book grew, Ashley chose to pause all of her ongoing client work – a staple of her business, Wayfinders Collective – so she could focus on promoting her book. Ashley went on a speaking tour around the world, on college campuses and at workplaces – Stanford and Google and so many others. She even had the chance to promote her book in New Zealand, a speaking gig that enabled a visit to see her dad Simon for the first time in 3 years. At every conference or event, Ashley led workshops to train people in her methods. She was interviewed by prominent thought leaders, and signed autographs at the end of every event and engagement.

“I thought I’d missed my chance at a fulfilling career,” one attendee at Ashley’s Carnegie Hall speaking event had mused. “But Ashley’s book and her inspiring story have taught me that I have every right to a career that makes money and makes me happy.”

Her publisher realized that Ashley had more stories to tell – and an audience who wanted to learn from her. They made a very lucrative offer for a second book, this time focused on proving to 40-and 50-somethings that their “time” wasn’t up; that they, too, could design their lives around purpose and fulfillment. Like her first book, Ashley believed in the power of this story to change people’s careers and lives, but she also realized that she needed time and space to write, think and explore the topic. Seizing on a dream she’d always had, she and her family moved to the Irish countryside for a year.

In Ireland, Ashley spent her mornings writing or on book-related virtual coffee chats, and the afternoons walking into town, shopping for dinner ingredients, and meeting new friends for brown soda bread and tea. Dan was able to work remotely, too, and using the time difference with the US to their advantage, they’d often spend the afternoons just the two of them – enjoying new experiences together and simply being with one another. Eli had managed the transition to an Irish Montessori school very well, and was starting to make friends and even develop a love of “football.” In between all of her writing, Ashley and her family took weekend trips to other European locales – Paris, Berlin, Madrid and many more. Ashley could see the positive impact this experience was having on Eli and who he was becoming – not to mention how it was bringing a new perspective and growth for her and Dan, too.

As the energy from her first book – and the public’s anticipation for her second book – continued to grow, Ashley realized it was time to build out her offerings and create the next iteration of her business. She created an online course – her second, actually – and it sold out in less than a day. She’d launched her first course, What Comes Next, in Fall 2021 – a goal she’d set for herself even before she’d turned 40 and one she was committed to achieving. It was built on the learning she’d done as a coach in her 30s: namely, that everyone feels stuck as they navigate transition. And that a simplified design thinking process can help anyone get unstuck and get going towards their dream life or career.

Building on What Comes Next, Ashley’s second course – Telling Your Authentic Story – became yet another flagship offering in a suite of online and in-person courses led by Ashley under her new business “Life Design School.” Some courses were held online, with exclusive coaching from Ashley herself via group video calls. Students also had the option to take their courses in person with Ashley; for a higher fee, they could meet Ashley and a small group of other “life designers” in Kauai, Sonoma Wine Country, and other beautiful locations for weekend retreats.

Knowing she couldn’t effectively reach and teach everyone, though, Ashley made the strategic decision that Life Design School would also offer training for other coaches and facilitators who wanted to become licensed in Ashley’s methods. With the help of Life Design School’s “Certified Faculty,” her methods would spread even further, faster, to anyone who was ready to use them to create meaning and fulfillment in their lives.

When her second book came out, Ashley paired that launch with the opening of Life Design School – and both were instant successes. “I feel like this book was written specifically for me,” one 40-something said after reading it. “I can’t wait to dig into everything Ashley’s sharing in our private Tuscany retreat this spring!”

As Ashley’s business and prominence grew, she knew she couldn’t do it all by herself. She started slowly, relying first on her publisher to help her build a book and promotional team around her. Soon, though, she hired an assistant to help her with scheduling and answering emails, as well as a social media strategist who managed her online presence. Over time, a small, diverse, committed – and fully remote – team of women came to call Life Design School their employer – from event planners to customer service reps. Ashley took her investment in these employees seriously, treating them like family. She’d set up her business for profit-sharing, so as Life Design School grew, so did their paychecks. In turn, Ashley’s business created opportunities for them and their families: putting their kids through college, paying off debt, enabling once-in-a-lifetime vacations and more.

Every six months, Ashley and her team would meet in person for a team retreat – time to relax and hang out together, but also time to recommit to their goals and imagine the future. At home, Ashley had commissioned a tiny house builder to construct a separate office to be placed in the backyard, near the back of her home’s property line. The space was comfortable and she felt creative, inspired and active there. There was also enough room in her office to host the occasional in-person coaching client, and an extra desk for Eli who would join Ashley in the afternoons to do his homework while Ashley worked.

Although Ashley was committed to spreading the word and equipping everyone with tools from Life Design School, she also knew that time was her only non-renewable resource. Once she and her family returned from Ireland, Ashley made a conscious decision that she would only work part of the year, from January through May and September through November. December, along with June through August, was reserved for family time, community work and volunteering, and mentoring and advising other young people who wanted to start businesses. Ashley knew this time off was crucial for her to rest, recharge, and set new goals for the upcoming work period.

These breaks also allowed her to reinvest her time and attention in her relationships – particularly with Eli and Dan, her parents and extended family like Andrea, and her close friends. She and Dan would plan family vacations during these times – to see family or visit friends in other cities, but also to get away just the two of them or with Eli. Once a week she’d meet with her team to check in on the business and hear any urgent or relevant news; otherwise, her team knew these windows of “away time” were sacred, and Ashley trusted her team to keep the business going.

Because of these restorative breaks, Ashley was able to be fully committed to work when she needed to be. Often that meant traveling for speaking engagements, but she was never away from family for more than a few nights. No matter what, she made sure to start her day with exercise, and end her day with family dinner. She was committed to not working on weekends or in the evenings.

When they returned from Ireland, Ashley, Dan and Eli settled back into their comfortable home in Surreywood. They’d been surprised to make so many long-lasting relationships so quickly, and the community had become like an extended family. Ashley’s mom Janice had moved into a retirement home nearby, and she joined the family for weekly dinners and regular visits to the Surreywood pool.

Dan had been excited about real estate investing for many years, and in late 2021 he led the charge on buying the family’s first rental property: a fixer upper on the Outer Banks. Over many long weekends and trips to the Home Depot, Dan had fixed up the bungalow and got it ready to rent on Airbnb. As COVID restrictions loosened in 2022, the cottage was in high demand, and Ashley and Dan made back their investment quickly. When it wasn’t being rented, the family would head down there for regular weekend getaways. They quickly started to make memories and feel connected to the beachfront community and environment.

Between her thriving business, Dan’s salary and the additional rental income from their beach bungalow, the family’s finances were solid. Every quarter Dan and Ashley would sit down and review their expenses – past and upcoming – as well as make a budget for the months ahead. They continued to be wise about where they spent their money, but both of them also came to enjoy spending their money in meaningful ways – whether that was on new home furnishings, delicious dinners out, and the occasional big splurge (like that time Dan bought Ashley new diamond earrings when her first book became a New York Times bestseller). They also committed to donating a portion of their income to organizations and community groups they believed in – particularly ones that supported families in need.

Mentally and physically, Ashley was in the prime of her life. She was healthy and an avid exerciser who loved building strength and feeling confident in her body. She ate well and got plenty of sleep. She took time to learn and pursue new knowledge through books, podcasts and conversations with other thought leaders. She had also continued to be screened by her doctors for early signs of breast cancer; after taking Tamoxifen for five years, she was starting to think about other preventative, perhaps more aggressive, measures to ensure her longevity and health.

Over the last five years, Ashley and Dan’s relationship had deepened even more; they were truly life partners in every sense. They had rekindled their romantic side – made even more possible as Eli got older, more independent, and spent more evenings away at Gopka’s! But even greater than that, they were aligned together on how and why they wanted to grow as people and partners. In an instrumental moment in 2021, Dan pulled Ashley aside and set the charge of creating a Vivid Vision for their family. Ashley, always the life designer, knew he was immediately right – and went straight to work creating this document.

For Ashley, the last five years had created more good fortune, more learning, more connection and more impact than she’d ever imagined. She knew she was lucky – and she didn’t take it for granted for a second. As she looked ahead to the next five years, she knew 50 was in her sights. “What a gift my life is,” she said, with a big smile on her face. And she truly believed it.