What’s A Money Coaching Experience Like?

I believe everybody needs a money coach in some form or another. Your money coach can be your spouse, parent, best friend, sibling, or mentor. He or she just needs to be a little bit more experienced and financially savvier than you. If not, she needs to at least be a good listener so they can reflect back on your blind spots.

Despite giving plenty of 1X1 financial consulting sessions myself, I've never had my own money coaching session. I view the entire Financial Samurai community as a great platform to discuss various issues. Some things I've learned from all of you are:

  • All talk, no action doesn't inspire change. Telling people to do something doesn't work as well as showing people through my own actions, e.g. posting 3X a week for eight years in a row, responding to comments at 5:30am, deploying capital based on my investment thesis, working towards my passive income goals, trying and failing all the time, etc.
  • Producing quality content without self-promotion actually works. I've often wondered whether it's possible to build a brand without being a public figure. Is valuing my privacy holding me back from maximizing my potential? Probably, but this site has grown every year since its founding in 2009, so I'm pleased with the progress.
  • Being a minority does not impede me from getting ahead in America. I came to America as a freshman in high school after spending the previous 13 years living in Asia plus one year in Zambia. Going from being a majority to a minority was sometimes a difficult transition. I highly recommend giving it a try one day. You'll build a lot of grit.

When Capital One reached out to me about their free money coaching sessions at one of their cafés in San Francisco, I jumped at the opportunity. Money coaching an help you better understand your relationship with money so you can pursue what you want in life.

I'm always interested in trying new things and getting feedback about myself in order to improve as a person. As someone who is struggling with money addiction, the timing of this coaching session couldn't be more perfect.

My one hour money coaching session didn't wind up being at their downtown Union Square Café, but at Pier 39 where they were hosting their Banking Reimagined Tour this past weekend. I was there to check out their huge state-of-the-art trailer when my contact at Capital One mentioned their San Francisco / Walnut Creek money coach, Megan CFP, was also there if I wanted to do my session.

It was a glorious day after a week of non-stop rain, so of course I told them “yes!”

Financial Samurai money coaching session Capital One
Having my money coaching session with Megan on a 60-degree and sunny day by the SF Bay.

Megan was great. She spent 10 years at Morgan Stanley as a financial planner, became a certified life coach, and decided to smartly blend her two skills together to help other people. Life + financial coaching seems like a rewarding career for anyone thinking about doing something new.

I've always talked about money as being a means to achieve greater happiness. I thought my end goal was always just about having absolute freedom, but through my first coaching session, I identified more goals.

The first step for self-improvement was to make my “travel plan.” Essentially, I had to figure out where (and how) I am today, what I have to do to get to point B, and what I think I'll have once I get there. Here's my travel plan snapshot. Pardon my chicken scratch as I hastily jotted things down.

I described my current state of being with the words: satisfied, happy, blessed, wonderment. Having a life partner, tennis network, online network, family, and home really bring me a lot of happiness and satisfaction. I plan to continue waking up early, working hard, and planning for the future so that I may have more happiness, contentment, satisfaction, and vitality! We talked briefly through each of the action steps.

The next step in the money coaching session was to either go through my Values or a Money Plan. Given I've got my money plan mapped out, I went with understanding my values. There was a list of ~50 different values to choose from and I was asked to write out eight that spoke to me the most.

My eight most important values are: Meaning & Purpose, Inner Peace, Belonging, Health, Independence, Equality, Freedom, and Helping Others.

Financial Samurai values

Next to each value is a numerical score between 1-10, indicating where I feel I am with each value.

1) Helping (10): Every day I feel like I'm helping someone with Financial Samurai, even if it's just a little bit. Even those who stop by and leave an angry or insulting comment probably come away feeling better about themselves.

2) Meaning & Purpose (10): As a result of helping others, I feel like I've got a good sense of meaning & purpose. Writing about personal finance just feels like a great fit due to my background. Mentoring kids also provides extra purpose.

3) Independence (10): Having my health gives me the independence to move freely. I don't ever want to feel like a burden to anybody. I know that day will come, but I'm trying to remain independent for as long as possible.

4) Freedom (10): Freedom to choose based on my values is all I ever want. Due to aggressive saving and investing, my passive income stream provides such freedom.

5) Health (8): So far, all my body parts are working. I feel no chronic pain either. My health score would be higher if I lost 10-15 lbs. Despite practicing portion control and exercising regularly, I'm still losing the battle of the bulge.

6) Equality (8): I strongly believe in equality for all. As a result, I'm constantly writing about issues that don't seem fair to get people to think more broadly. For example, why is there a marriage penalty tax? Why do Asian people have to do better in school to have the same chance of getting into university as other races? Why do people have the ability to vote on legislation that raises taxes on other people without having to pay more taxes themselves? Why is there any poverty within 30 miles of a billionaire? Why do we gorge ourselves when there are over 200 million malnourished people in the world? Why do CEOs make millions killing people by selling sugary drinks and unhealthy food?

7) Inner Peace (8): The older I get, the more often I ask myself whether I'd be OK if I died today. The more I'm OK with passing, the more inner peace I have. I got close to being OK dying young after achieving my life goal of doing something entrepreneurial. Having life insurance and a clear will also helped. But now that I'm thinking about having a kid, I want to at least live long enough before he becomes an adult.

8) Belonging (6): Here's where I feel I'm most lacking. It's interesting I feel this way due to the relatively large Financial Samurai community. Perhaps due to the fact there's such a large online community, it makes my offline community feel very small? I truly enjoy interacting with the millions of Financial Samurais around the world who take ownership of their lives.

I'm a pretty social person who loves to hang out with cool people. I miss the days when I could just meet up with a friend after school and skateboard for hours on end without a care. In a way, retiring early has robbed me of camaraderie because I no longer have a group of colleagues to hang out with during and after work. There are no more power lunches with friendly clients either. Oh how I miss using the company corporate card. Almost everybody I know has to go to work, and it does get lonely at times.

Relationships take effort. Therefore, I plan to do two things:

1) Plan a couples retreat for my 40th birthday. I really enjoyed going with two other couples to Indian Wells last spring for a tennis tournament. We rented a sweet house with a pool and hot tub (pic below), went out to eat every night, and watched world class tennis during the day. So fun! But since then, I've only had three dinner outings with couples. So sad.

Our couples retreat rental house in Palm Springs. Such an awesome time!

2) Identify two things I love and attend weekly meetups. There are endless meetups here in San Francisco across a variety of interests. I'm pretty tapped out on the fintech / startup scene, and I've got the tennis community covered. I'm thinking about joining a co-ed softball team where we play some random opponent on some random field and go for brewskies at a dive bar after. I'm also considering joining a car club after I buy my mid-life crisis vehicle. It's fun to drive in a cavalcade up to wine country with some car fanatics. We can create a mid-life crisis support group!

Finding Direction And A Recommendation

It's interesting to learn my money coaching session wasn't so much about my finances, but more about how to achieve life goals. I plan to meet Megan for one or two more free sessions next time I go downtown for some business meetings. It feels great speaking to someone who is 100% focused on helping you move forward.

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About The Author

35 thoughts on “What’s A Money Coaching Experience Like?”

  1. I was just talking to my girlfriend about lack of connection to community and purpose seems to be the root cause of so many ills. This conversation was in response to reading another book about addiction. I wish I could figure out more ways to solve the problem now that I see it.

    Seems like life coaching was a useful tool for you. Thanks for sharing your journey with us.

  2. FinancialBlogLurker

    Spurred on by your post I went to the Capital One Cafe that recently opened where I live in Boulder, CO. They were still in the process of hiring a financial coach but gave me a coupon for a free coffee, yay! Hopefully they will stay open as our City Council recently recommended banning all banks on the Pearl Street Mall to encourage local businesses to locate there.

  3. Amy Dunkelman

    Hello Sam…although I am a new subscriber to your posts, I so enjoy the “humanity” and emotional side of your post here. I am not anywhere near your, and likely many of your reeaders’ level of financial independence (although I hope to be someday!), I truly appreciate your openness about the compassionate and living side of your writings. Your section on Inner Peace I believe is so very important, and often so lacking in many people’s hard quest for lots of money and the toys associated with it. Too many people think that the simple acquisition of more and more material goods will bring them happiness, which, of course can lead to great emptiness and a greater feeling of lack. I say, keep pursuing BOTH your financial independence and inner peace and contentment. The sharing with and giving to/connecting with others is the key as well! I dont know your age, but I think you are an old soul on the right path in many ways.
    Thank you for your posts, I appreciate them greatly.

    1. Howdy Amy,

      Thanks for being a new subscriber! Always nice to meet new folks even after all these years.

      I’ll continuously work on my inner peace. It seems to get easier the older I get. When you’re young, you’re anxious and feel like you need to prove yourself. When you’re older, you start achieving your goals so there’s less angst.


  4. Sam… Re life insurance, although it seems a relative no brainer to buy a term policy, I suppose you don’t really NEED life insurance if your investments are already producing significant passive income. Would you agree?

    1. I disagree. I love the idea of having my loved ones receive a tax free windfall to help ease the pain of my early demise. Term life insurance is pretty cheap. I will also die happier knowing that I will help my loved ones be more financially secure after I’m gone. It’s like my last gift. I’ve got a lot of assets that are complicated. Maybe the government confiscates them or the courts tie them up.

      The insurance co might screw me too. But, the more things I can leave behind, the higher the chance my loved ones will ultimately get something from me.

      Related: How Much Life Insurance Do I Really Need?

      1. One of the other reasons to carry a term policy even when technically financially independent is that a serious illness could drain you financially even if you carry health insurance. The term policy could then still help provide for loved ones after your demise.

  5. Interesting perspective. How is a financial coach different than an financial planner/adviser? I’ve met with the latter a couple of times and they said I’m doing everything I should be at my age (e.g., putting $$ in 401k, after tax savings, have life insurance, emergency savings, etc.). They were like “well….I don’t really know what else to tell you”, lol. Unfortunately, there isn’t a C1 cafe in my area, but my credit union is offering a free consultation, maybe I’ll sign up for that!

  6. I’ve never had a money coaching session myself. My husband pushes me on my personal and joint goals but I’m sure someone independent would shine a light on a load of stuff I’m ignoring- intentionally or accidentally. And my dad, who is fastidious with finances, often quizzes me on what I’m “wasting my money on now” so that keeps me thoughtful in many respects.

    I’m more of a country bumpkin than a city slicker, and personally find I feel more alone in a city than I do in the countryside. Maybe because there are so many people that I’m not connected with in the city, whereas there are less to connect with in the country, hence I am aware of how many people I’m not connected to in a city (if that makes sense?) Also… any excuse for a couples’ retreat :)

    1. Makes sense to me. And thanks for pointing out the typo. I also need help.

      It is ironic that the more people there are, the more you may feel alone sometimes. So your analogy of the city vs countryside and my analogy of my online network vs. my offline network are very similar. The juxtaposition makes one feel more alone.

      Without my online network of friends, I’d spend more time w/ my offline network that will also seem much greater.

  7. robert clayton

    I have had 2 financial reviews and found both totally worth my time. The first one cost me $500 and was worth every penny. The second one was free and extremely helpful. I will admit of the 2 the one that cost me money was superior. I look at paying a certified financial planner like paying a physician for a annual wellness check. You have someone look over how you are doing and see if you are going in the right direction. Also they should make sure try to help mitigate risk as much as possible (will/estate planning, umbrella policy, disability/life insurance).

    On the weight issue I recommend less carbs, and strength training. I just turned 48 and both help, but will not stop the bad of the bulge. I use to be cardio only, and it doesn’t solve once you hit the big 40.

    1. Glad to hear about your financial review experiences. I totally agree that we should have a mental health checkup and a financial help checkup every so often. It is very easy to get of course and COMPOUND bad mistakes if you have no guidance.

      It’s why a little overeating here and there leads to big guts over time. Same thing with bad financial moves here and there could lead to massive financial waste. So worth spending the time and money to get some help.

  8. I think I saw something on your list about “father-related” reading. I have a suggestion of an area to explore – not money-related, but at least number-related! This is the “word gap” which establishes a lifetime of success or struggling for kids.


    “The term “word gap” was first coined in the 1995 Hart/Risley study that found low-income children are exposed to 30 million fewer words than their higher-income peers before age 3. This study and others have linked poor early literacy skills to lifelong academic, social and income disparities”

    If you can talk to your child as much and as intentionally as you write to us, I think you can do more for your child than the most expensive private schools.

    1. That is fascinating! I have never heard of word gap before. Thanks!

      Given I don’t have a day job, except for high school tennis in the afternoons now, I should have lots of time to talk and listen to my child. Being able to spend more time with children is a huge reason why I’ve engineered this lifestyle.

      I’m excited to be present for my child during his/her most precious stages. How cool would it be to have a dad who is always there to listen, guide, and mentor?

      1. It’s amazing how children expand our life experience and give a deep sense of connection and purpose. You’re right, the early stages are precious (and exhausting).

  9. Sounds like a fun experience! I’ve never had a formal money coaching meeting before. It makes sense to get feedback and gain some new perspectives in the process. That’s cool Capital One is offering this money coaching service for free. I’ll have to try it out next time I’m downtown. Their cafe is a great hangout. Every time I go there are always a lot of people but there’s still always seating available to check email, have a coffee, use the atm, etc.

  10. Given how much I’ve benefitted from mentors in my professional life I’ve always thought that it would be great to have a financial mentor – someone who knows my finances and also knows me, and can therefore push me to do better in ways that are compatible with my strengths.

  11. Really interesting! I would like to do some coaching when I’m a bit less busy. It’d be great to help some people find their way around money. Do you know if there are some training or certification for this? The material looks good. A bit touchy feely, but probably good for coaching.

  12. Sounds like fun! It’s always great to get a 3rd party opinion and advice on your plans, be they financial, life, or otherwise.

    It’s hard being social in Silicon Valley outside work since so many people are so caught up with their jobs. I’ve found meetups to be a great way to meet interesting people and make new friends, like the time I attended a Cash flow meetup. Good times.

  13. Sam, cool that you were tapped to be a money coach. People need that level of financial mentoring nowadays. Is this something that you are going to do regularly?

    Another banker and I have been kicking around the idea of doing occasional financial education seminars for kids/teens, low income adults, and other under served groups. But we don’t have any real education experience. As someone who is now a world famous money coach, any advice you can give so that we are able to provide the most value for anyone who comes to hear us speak? As bankers, we’d primarily be speaking about managing your bank accounts, budgeting, and building credit more than anything else.

    ARB–Angry Retail Banker

    1. Action Jackson


      My wife and I taught Financial Peace through our church; there are many other similar programs. interestingly the vast majority of attendees were minorities.

      Our first series we were a disorganized wreck, then we got better each time we started the series over again. May be helpful for you to find a program that you agree with the material and start with that until you can hone in on your own material. Good luck!

  14. The Green Swan

    I’ve never had a life official finance coach (unless you consider my brother who I speak with often about finances). I think it says a lot that someone even like yourself who is very knowledgeable and stable with retirement to seek this out. We can all use some outsider perspective. Does Capital One offer these sessions across the country as well?

    1. They offer them wherever they have a Capital One Café. Check the directory that I linked to. Pretty cool value add b/c I’m sure a ton of folks could use someone to talk to about life and money. I bet they will be overwhelmed with demand b/c I know there is this underlying money anxiety across the nation.

      One common anxiety is this: It’s a bull market. It seems like everybody is getting rich except for me. What to do?

      Related: Investment Ideas At The Top Of The Market

  15. Go Finance Yourself!

    Never thought about a life coach. Looks interesting, but my question to you is, do you think you would pay for it? How much value do you think there was as opposed to just a fun free activity?

    As far as a financial coach goes, I’ve never had an official one, but my dad is someone I’ve always been able to learn from when it comes to finance. He tried to get me to start investing back when I was in high school but I didn’t have any interest then. When I graduated college he gave me The Automatic Millionaire by David Bach, taught me the rule of 72, and stressed how important saving early was.

    1. Financial Samurai

      The more you are lost or in a period of transition, the more valuable a life/money coach is. If I was actually going through a mid-life crisis, I’d most certainly find a professional who deals in such situations to work out my issues. Sometimes it’s hard to open up to your family and friends.

      Other milestones include:

      * Burning out at work
      * Coming into a large sum of money suddenly (big promo, inheritance, etc)
      * Burning out from your entrepreneurial endeavors
      * Feeling aimless
      * Going through bankruptcy
      * Going through a divorce
      * Having children
      * Parents dying


      So many things happen in our lives where we not only need the support of our friends and family, but should also seek people who’ve trained their whole lives to help people find happiness.

      Anecdotally, I took off my financial coaching link from my About page because there was just too much demand.


      1. I volunteer as a money coach for a non-profit (free service for lower income individuals) and also have a money coaching business focused on helping working professionals in addition to my career in corporate finance.

        I spend a lot of time listening to clients to help them identify their current financial situation, concerns, past habits, and goals. I then work with them to implement simple effective money habits that will help transform their financial situation so they can achieve their goals.

        What I have found over time, is that the majority of clients really just need someone to be their money accountability partner and help keep them on track over time. I have also noticed that most people feel more comfortable opening up to a “stranger” than friends or family if their situation is less than ideal.

        While paying for a money coach is still a fairly new concept, as opposed to paying fees or commissions to a CFP or advisor, I feel that coaching puts the client in control of their money and provides a lifetime of value. The best thing about getting help from a coach is that you learn new skills and develop habits that you can use long after your work with the coach has ended.

  16. Erik @ The Mastermind Within

    Hey Sam, I really enjoyed your story – it hits on the “personal” side of personal finance. While not that high on your list, inner peace, do you meditate? One of my friends has been focusing on mediation and yoga as a way to stay flexible, recover faster from his workouts, and connect his body and mind.

    To your point on equality, I want to educate other people on various “lies” we’ve been told throughout the years… one that sticks out: 11 servings of carbs is NOT what humans need to be healthy. I’ve been eating higher protein and higher fats (I’ve been eating way too many almonds, peanuts, etc.), and I feel great and look great. Give it a shot!

    1. I used to meditate before going to bed each night. Not any more. I need to start again. I got a massage for a V-day present and the masseuse kept on telling me to breathe (150 times in 70 minutes, kinda annoying) and told me to meditate.

      I also need to do more yoga. Lots to do!

  17. It’s really interesting watching (reading) you evolve over the years, especially since I can relate to many of the values you described. In my opinion, you were really focused on financial independence in the early days, and still are, but now you’ve shifted more to a focus on true happiness and contentment. It reminds me of Maslow’s hierarchy of needs. You needed to reach financial independence to enable you to focus on the other areas. Or maybe I’m projecting a bit, I’ve always imagined that’s what the evolution would look like. Either way, you’re still spot on!

    1. Yeah, once you get the money thing out of the way, folks start focusing on purpose. There’s really no better feeling that to help someone out. Having a portfolio of personal finance articles online is almost like a perpetual giving machine.

      I see all comments left for all articles on my dashboard. And more often than not, there’s something nice someone has left on an older article that makes me feel happy.

  18. Joe @ TheWellExamined.life

    I think you lack of belonging is a common issue today. Even for those who work, have a few good friends, or live an active life.

    The problem is that having good friends makes us feel connected, but not necessarily connected to something LARGER than ourselves. You might get this a bit through your tennis club, but those interactions might lack purpose. You surely get this through the FS community, but this lacks a tangible human element.

    I think there is a role for ‘fraternity’ to make a comeback. My grandpa was a Lion. My wife’s grandpa was a Moose. There are Elk, Shriners, Freemasons, and more. These clubs–where they still exist–are dying. They are full of octagenarians wandering from room to room and touching the walls.

    I think they fill a real need, though: They offer camaraderie, betterment, community, and a connection to something larger than ourselves.

    I’ve started a small version with a loose network of friends and acquaintances. I call it AMDAT (awesome men doing awesome things). We meet once per month for a predetermined activity. As the group grows and stabilizes, I’d like to see it shift from entertainment (golf, paintball, yard parties) to include an aspect of ‘giving back’. It brings me deep satisfaction to be part of this brotherhood and fills a real gap in my life.

    1. AMDAT! Sounds like a fun group to be a part of. Hard to beat paintball sessions in the woods. Did that about 10 years ago and it was so, so fun. The woods/jungle is better than the artificial arena imo. Fun to lie down in the dirt, go into triangle formation with your buddies and try to capture the flag.

      Lead the giving back charge! I’m sure your group will be on board.

    2. Repeat after me: Co-workers are not friends.

      We did something similar called “Pie Club” where the entire premise was to do awesome stuff like eat pie and race drones.

  19. Brad - MaximizeYourMoney.com

    Very cool – thanks for sharing that. I agree that money coaching isn’t just about math and finance… it’s really about emotions and behaviors. When a coach spends all their time talking about money and not your goals and priorities, it’s likely a sign that it isn’t all that great of a coach.

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