September 15, 2025
Filed under: Business Owners, General
Often when we talk with clients about living a life without regrets, the first thing we will hear is “I’m blessed, I can’t/shouldn’t have any regrets.” As we dive deeper into our life planning work, we often find that there IS a regret…somewhere. Sometimes it’s a missed opportunity or a lost relationship. Sometimes it’s seemingly unfixable.
What Does It Mean to Live a Life Without Regrets?
In “The Power of Regret”, Daniel Pink talks about harnessing regrets for good: confront them, learn from them, and use them as a guide for future decisions. At Omega, we take clients through a meaningful “life planning” process to help identify both past regrets and things they might miss without greater intention and then build an intentional human-centered wealth planning strategy to help them create the opportunity to live life without regrets. Whether it’s mending a relationship, rebalancing work and family, or taking care of one’s health to be around for years to come…we are living a more intentional life, deploying our wealth in service to these goals rather than keeping the focus on money alone.
Successful Business Owners & Execs Often Have Regrets
As a business owner, I understand the regrets all too well. Late work nights, vacations cut short, one more email… often there are many sacrifices and subsequent regrets for business owners building their businesses. Likewise, successful executives face hard decisions around travel and meetings, and simply balancing the focus between life/family and their careers. At Omega, we help successful people stop to thoughtfully examine those regrets, not to feel bad about them, but to harness a sense of purpose and what’s important in their lives and then to align their wealth and life with those priorities. Money only takes us all so far. An intentional life can be much more powerful and fulfilling but it takes effort and support to get there.
Creating an Intentional Life
Through a series of discussions and exercises, we learn about the dreams that have gone unfulfilled, the wish that seemed too big, the plans for the business that just never seemed to materialize. Asking “what would change in your life if you only had 5-10 years to live?” or “what would you regret not having done if you only had 24 hours to live?” brings a focus and deep understanding of what’s most important to you. Asking a version of these questions to business owners can often bring out the long-desired wishes & goals for their business, re-invigorating and focusing their efforts much more productively. Once we have these discussions, our clients are inevitably positively impacted, and often will begin making different choices in their lives.
A Business Owner Who Made a Different Choice
Earlier on in the business after I had been trained in the Kinder life planning work, I worked with a couple where the woman was a very successful business owner. The regret, as we went through the life planning exercises, was that she had not been a very nice boss. She built a valuable business on the backs of her employees. Now, as she planned her exit strategy, she had a number of choices. An external sale for the most amount of money or an internal sale, to her employees in the form of an ESOP (Employee Stock Option Plan). After going through the life planning work, it was clear to her that the ESOP was the right choice to make things right. While she couldn’t change how she had treated her employees earlier, she could move forward intentionally to make things right professionally, personally and financially. That is the power of regrets – to use them to make different choices while aligning your money with what’s important to you.
Aligning Money & What’s Important to You
For every individual and family, what’s important is different. It might be having a big impact within the local community; it might be funding your own creative efforts or that of other family members. It could be supporting educational or spiritual pursuits. Unlike life coaching, we are able to bring our financial skills to help support and guide our clients toward building a financial life strategy that harnesses their wealth in service to vision and values for themselves and their family. How you spend, give and even invest your money can change. We at Omega are here to help guide, partner and empower you to a fuller life through the alignment of your money and what’s important to you.
Here is an easy-to-read PDF that you can view, download and even share with anyone you know who might benefit.
lisa