When You’re at a Fork in The Road; Re-inventing Your Life and Legacy

Kelli Richards
6 min readMay 28, 2021


When the Magic Question is: What’s Next? (Reinventing Your Life Around Your Values, Passion and What Matters Most as Your Legacy)

photo credit — Matt Swafford

We all come to a crossroads or an inflection point at different stages in our lives — it could be a college graduation, a wedding (or a divorce), the birth of a child or the death of a parent or loved one, or on a happier note a successful exit from a start-up — or “retirement” (which I refer to as “reinvention”!). When we reach these junctures at key milestone moments in our lives, it’s natural to pause and reflect on what’s next. That becomes a catalyst and a wonderful opportunity to re-invent ourselves and our lives around what matters the most for us at that stage as we evolve along our unique path.

In my role as a Trusted Advisor, I’ve worked with scores of high achievers from start-up founders to rock stars, to athletes and successful innovators, to media and tech execs — as well as regular folks who are perhaps more anonymous. Once these individuals have amassed a certain level of wealth and financial freedom, they start to give serious consideration to what they want to create at this next stage of their life — typically around what will be most fulfilling for them. They often seek to craft a life that’s more balanced between family and work, around their values, passions/hobbies they may once have cherished but never made the time for. They’ve earned the right to have fun and play (!).

If they’re really mindful and in touch with themselves, it nearly always comes down to crafting a life that matters most to them day-to-day near-term and in terms of having an impact over time (their legacy).

Hit the Reset Button and Thrive

Every week it seems I’m in touch with individuals who either are in the process of re-inventing themselves or have successfully done so — some whom I’ve helped directly and others where I’ve observed them having a successful transition on their own. Just this week I re-connected with a very successful former VC in Silicon Valley who has re-invented himself as a filmmaker; in his next act he’s re-located to LA, has launched a production studio, is producing profitable films and he has never been happier.

A couple of years ago, I was at an invite-only intimate gathering with Sheri Salata, Oprah’s long-time exec producer of the TV series and former President of OWN Networks. Sheri had recently left the ultimate job (after 25 years), moved to wine country, and had just published her first book entitled “The Beautiful No” about how her choices have led to where she is now in a full-on re-invention of her life today — all based on what’s feeding her the most at a soul level at this stage of her life and her work.

Stewart Copeland, the founder & drummer of The Police, is a long-time colleague, client and friend. When The Police disbanded, Stewart took a left turn and created a successful career as a film composer. Today he spends his days hanging out with his rock star pals making music on their own terms from his glorious home studio attached to his home at his private compound. And from that place he is at complete choice — scoring operas, ballets, and performing in super-groups with his pals performing at inspired locales.

Awhile back I met up with Meg Whitman who has had an amazing career as CEO of eBay and HP in Silicon Valley, ran for Governor of California, and had re-located to Hollywood to serve as CEO of Quibi with Hollywood mogul Jeffrey Katzenberg of Disney & Dreamworks fame as her partner. Meg clearly doesn’t have to work anymore, but was doing this as a creative challenge because she was inspired about what was possible & was having fun. Unfortunately Quibi proved to be ill-fated and short-lived, but I’m confident Meg will once again pivot and move on to the next chapter of her journey.

Ronnie Lott (All-American football champion) and I have become friendly as he and I share a local coffee shop as our “Cheers” hang-out for many years. After his career ended playing football actively, he re-invented himself by becoming a TV sports analyst, launching a VC firm with several of his SF 49ers pals, bought & runs car dealerships, and is an advisor to the current roster of coaches and players on the SF 49ers team. He’s made a successful transition to balancing family, business and giving back not only to the 49ers but to many worthy causes. Ronnie is truly living and loving his life fully.

Three Considerations When Exploring What’s Next

1. Take Time to Take Stock

It’s a good time to reflect on what’s most important to you at this stage of your life and work. Do you want more time with your family? Do you want to travel more? Do you want to be part of a start-up or launch a foundation or write a book or produce a play? All options are on the table. What’s most important is to know that while you can have it all, you may not be able to have it all at once. Some things take longer to create/put in place.

The important thing is to craft a life around what matters most to you.

2. Back to the Future

Do you have some passions or hobbies that have taken a back seat to your fast-paced life for various reasons (for years, maybe decades)? Now’s the time to dust those off and consider how you can weave them into your life and make time for more fun in your life.

3. Build Your “Round Table” of Support

What resources do you need to make your vision a reality? What support do you need from your family and others to get them on board? You don’t have to do everything on your own; discuss and share your vision with others and enroll them in co-creating this new life and opportunities with you.

But when you do be careful you share your dreams with those who you know have your best interests at heart; you don’t need any nay-sayers.

How a Trusted Advisor Could be a Major Asset as you Pivot

I’ve been honored to be a Trusted Advisor to some extremely talented individuals, several of whom are among the most successful and extraordinary people on the planet. And many others who are ‘normal’. You might ask why these individuals would need an advisor. The truth is they don’t necessarily “need” one, but they want one. Virtually all successful athletes and business executives surround themselves with top-notch coaches and advisors.

No matter how successful, intelligent, resourceful or wealthy you are, it’s important to have someone in your life who has your back, sees your gifts, shares your vision, and most importantly challenges your assumptions and old mindsets that no longer serve you, and is willing so say things that no one else in your life will say to you. They will call you on where you hold yourself back, and they will help you navigate and co-create a blueprint for where you’re headed in the future based on what you say is most important to you. They’ll be great listeners, be genuinely curious and interested, and will ask you powerful questions that will have you saying “I’ve never thought of it like that” or will offer re-frames and insights that will spark “a-ha” light bulb moments that could become game-changers.

I’ve been fortunate to have had some powerful advisors, mentors and coaches throughout my own journey — including the late great Steve Jobs, Alan Cohen, Alan Weiss and Bill Campbell (aka “The Trillion Dollar Coach” — see the new book which just came out this month about Bill’s legacy and impact in Silicon Valley, authored by Google Chair, Eric Schmidt).

If you or someone you know could benefit from this type of support, and are interested in having a conversation, contact me and we’ll connect. I thrive on having the opportunity to work with successful high achievers (and those who strive to be), especially when they’re at their own threshold of ‘what’s next’!



Kelli Richards

KELLI RICHARDS is a seasoned ’super-connector’, a trusted advisor & a strategic bus dev exec bridging innovators & creatives. Learn more at “kellirichards.com