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  • Writer's pictureMaestro Associates

Meet Maestro //Chris Blair

Updated: Jan 11, 2023

For most people, money causes anxiety. From managing debts to budgeting, saving, investing, insuring, and paying taxes — every dollar you make can feel like it has red tape attached to it. When it comes to money, it’s no wonder so many of us aren’t sure how to make the most of it.

But when you sit down and talk to Chris Blair you don’t feel like you’re talking about money, finance, or retirement. Chris has an easy way of asking you about your life. And as you meander through the past, the present, and what you hope your life may look like in the future you start to unravel things about yourself you may not have known. And how those things affect your idea of financial aspirations, confidence, and even frustration.

It’s no wonder a recent post on the Maestro Facebook page credits Chris for being part financial planner and part financial therapist.

We asked Chris to share some of the emotional drivers that often affect people’s financial thinking–whether they are aware of them or not.

1. Past experiences, behaviors, and habits explain a lot of decisions today.

Often in getting to know clients we talk about how they were brought up. Family values, how money was treated. And what “money” has meant for their life. Whether the client I’m talking to is a struggling start-up business owner with a first child at home or a multi-millionaire dealing with generational wealth, early observations, influences, feelings, and emotions about the handling of money, make their way for good (or sometimes not so good) into their present financial life. So we talk about those things. Because no two clients have the same pressures or objectives. But all clients want to feel in control and that they have good choices to make, no matter what the world throws their way.

2. Pressure in the now prevents us from acting now and feeling more confident about our futures.

It’s no surprise that many Americans don’t save and build their resources as they should. Financial planning is something everyone can use. And the earlier you start the better. Many people feel they must have a substantial pile of money somewhere to begin planning. And that just turns into an “I’ll start then instead of now” strategy. People often don’t know where to start. I also see that it’s very hard for many people to focus on the future. We all face a lot of issues and pressures just to get through the day or week. Job and career changes, environmental pressures, new cultural shifts, political unrest and a pace of change in both technology and finance that is opening new opportunities as well as risks.

Another common thing we discover in early conversation is that spouses or partners sometimes don’t agree as much as they thought they did. For example, I commonly see that one partner may be focused very much on getting to the end of the week or month–and be really good at it. That’s everything from managing family medical appointments to figuring out what’s for dinner or making all the arrangements for an upcoming vacation. The other partner may have a longer focus. Often that other partner has little idea of the pressures that take place every week. But they feel the pressure of what life will look like far down the road. They’re not thinking about the family vacation. They’re wondering about the family vacation home. And if that’s a dream they can accomplish. At Maestro before we talk about anything financial, we take the time to talk about those very important things. It’s the only way to arrive at a strategy that makes both parties feel comfortable.

3. People tend to have a set and forget mindset when they think about financial planning. But that's not how the world works anymore.

20 years ago, people were dreaming of a stable retirement. We’ve all seen it in advertising. It’s the handsome and fit couple walking hand-in-hand on the beach without a care in the world. But those were different times. Our parents spent their careers at a single employer, earned pensions, and were able to feel confident about choosing to end their working careers. They also had lower healthcare costs–and to be frank, didn’t live as long.

People still come to me and ask, “how much do I have to put away each month to get to X by a certain date?” That strategy may have worked well for their parents, but today control and confidence come when our clients realize that financial planning is as much about today as it is about tomorrow.

Today, our clients change jobs and even careers frequently. They move in and out of the gig economy. And many of their employers don’t even match a 401k. And so yes, we have to take a self-reliant approach to retirement planning. But part of that picture needs to be planning that also delivers important choices and freedoms now. The right planning means knowing you can walk away from a toxic boss. Or choose that you deserve to walk hand-in-hand on the beach this year–not just in your far distant future. I recently had a client who was very anxious because he made the decision to shut down his small business. He was very concerned that he wouldn’t be able to stick to his previous financial plan. Imagine his surprise when I suggested that he take 6 months to think about it. I reassured him that he had been saving his whole career for a moment like this. And rather than being consumed with the anxiety of failing to meet the commitment of his previous plan, he should put all his energy and focus into what he wanted to do next. That’s exactly what he did. Within four months he found an opportunity he wanted. And within a year he was right back on track.

4. People expect a financial planner who wants to read spreadsheets. Not their emotions.

Financial planning is about goals. More often than not, the goals aren’t about money at all; they’re about time spent with loved ones, vacations, retiring earlier than expected, or leaving a legacy you’re proud of.

Once we understand those deep emotional goals we look at “the how”.


Identifying what is most important to you in life, where you want to go, and what you want to do along the way.


We bring all the pillars of your portfolio— personal budgeting, money management, insurance, tax accounting, retirement savings, and estate planning into a comprehensive, flexible, and confident plan.


Every six months we meet to review progress, life changes, and alignment to the plan. We balance personal and financial needs and adapt the strategy accordingly.

When our clients understand the big picture, they feel in control. And when things change, and they always do, all it takes is one phone call to tailor their entire financial portfolio to meet that change. The result is far more than a healthy balance sheet, it’s a whole new level of simplicity, confidence, and peace of mind.

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