Gameplan 2020: Align Your Money With Your Unique Vision of Success

By: Ryan P. Dolan

“Man pursues a great variety of goals, but the one he seeks as his ultimate end is happiness.  Everything else is a means...”

Socrates

As we approach the last month of the year, now is an ideal time to reflect on 2019 and to gamplan the year ahead.  When it comes to your money, strive to transcend superficial resolutions and goals. You owe it to yourself to think deeply about what success means in your life-to you specifically.

  • Do you feel in control of your finances, or do you frequently feel like money is controlling you?  

  • Do you have a well-articulated vision of what success looks like in your life and a clear understanding of money’s role in that?

  • Do you have a blueprint of a life well-lived and a roadmap to get you there; one which balances your deeply-held needs, goals and aspirations today with those decades in the future?

These are not easy questions to answer.  And yet, in my opinion, taking a proactive, holistic and highly-integrated approach to answering them is absolutely critical in gaining mastery of your money.  

I was talking recently with a friend, Jim (his name and details have been changed), a particularly well-adjusted, thoughtful guy.  By almost any benchmark, he had achieved considerable professional and financial success. While we talked, it became apparent that something was bothering him.  When I asked, he admitted that while he couldn’t pinpoint the cause, he was experiencing persistent feelings of anxiety and lack of fulfillment. After an extended conversation, with a lot of questioning and listening on my part, we started to unravel some of the symptoms.  

When asked to think about his work, Jim admitted to being driven by feelings of insecurity and a deep fear of failure.  Despite his success, he was often plagued by feelings of guilt and unworthiness, of being a fake fearing inevitable discovery. He worried about everything being taken away from him. His default response to those feelings had always been to work harder to “deserve” his success.  As a result, he worked grueling hours, and increasingly felt less time for anything else, including his family. Worse, even when he was with his family, he wasn’t really present, and was usually distracted by thoughts of work.    

Jim had always taken pride in his role of provider for his family, giving his wife and kids the lifestyle and financial security he didn’t have growing up.  However, with his two kids now in high school, and soon to be out of the house, he felt pangs of regret at what little time he had spent raising his kids and building connections with them. He was beginning to realize that his life was deeply unbalanced.  He tried to ease this regret by providing his kids a lifestyle he never could have imagined when he was growing up. The problem was, his kids lacked any real appreciation for money, and very little gratitude. Jim worried about their level of initiative and drive, something that his own childhood had instilled in him.  

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In general, Jim didn’t really feel in control of his life.  He never had time for anything. He invested so much time and energy in his company, that while he was financially successful, he was incredibly time poor.  At times it felt like his company has limitless demands and had overtaken his life. His health was an area that had clearly suffered. He had put on 25 pounds over the years, and used food and alcohol to cope with the pressures of work. He used to love to play tennis and mountain bike, but hadn’t done either in years.  Was this success?

Finally, Jim felt he wasn’t living the values that were important to him.  If he was honest with himself, his financial success had become a goal in and of itself.   Success now simply meant “more.” He admitted that money was increasingly being used to gratify his ego, and wasn’t be used in service to others.  He was raised in a family that always put a high priority on charity and giving, both in time or money, in spite of his parents’ modest means. His parents walked the walk of their values.  At best, Jim gave money half-heartedly. Lately, though, he had felt an increasing pull to start giving more, with more meaning, but was unclear how or where to start.  



Jim’s situation is far from unusual.  Money is a wonderful servant but a terrible master.  It’s been my experience that when people make financial success the ultimate end in their life, the result is often unrealized potential, anxiety, a lack of real fulfillment, and regret.  It is absolutely critical to engage in a process which allows you to unpack what your unique version of success looks like. This is not always intuitive, or something that can be done quickly.  And in my biased opinion, it usally can’t be done on your own. Often, when I work with new clients in this discovery process, it results in quite a bit of client self-discovery, where clients dig deeper than the superficial, and tap into a much deeper vein of values, motivations and priorities.  

Admittedly, it takes some time, introspection, and accountability on the client’s part.  Many say they don’t have the time. In my opinion, they don’t have the time not to think this way. The only rational time to do this is at the outset of the advisory relationship, well before any new courses of action or strategy can be determined.  “Begin with the end in mind,” as Stephen Covey says. We always prioritize a holistic qualitative understanding of the client before we look at the quantitative numbers. 

Jim’s example is very common with high-performing, career-driven people.  For many, success and accomplishment can quickly morph into the goal itself, which will solve every other issue in their lives.  To be clear, career and financial success are very important. Ultimately, however, they are there primarily to serve larger purposes. For Jim, money wasn’t serving his life, rather his life was serving his money-and the results were causing serious problems.  While the course of treatment will ultimately depend on Jim’s unique situation, step one for him was admitting there was a problem.  



As you look to 2020, consider how aligned and integrated your money is to your vision of a life well-lived.  Ultimately, money should be a means to foster the ends in your life that really matter. What those ends are is unique to you.  Start today.

www.dolanpartners.com