Six Figure, Breadwinning, Millionaire Moms – Wish I Could Surf

Good morning and welcome back to another breadwinning, six figure, millionaire mom interview! Today I have a great story from the amazing anonymous woman “wishIcouldsurf” – she’s stopped by the blog to read and comment in the past, and reached out to share her story. This is a fascinating one, where she tells us about her journey as a single mom, working in the male-dominated field of banking, and has now reached financial independence – retiring in just a few months! I love reading about women on FIRE (Financially Independent, Retire Early), and this is no exception. Be sure to read on through the end and leave her a comment if you’ve also enjoyed learning about her story.

So without further ado, lets hear her story.

Tell us about yourself!

I’m a 44-year old financially independent lady with a 9 year old daughter.  I got separated and then divorced from my first husband when my daughter was 6 months old, spent some significant time as a single mom and remarried last summer. Those single mom years were formative in that I took complete control of not only my personal finances but also my investment management.  I previously paid a financial planner since I “didn’t have time for it” (what was I thinking???) and spent time understanding my own desires and goals and from that point stayed focused on what was best for me and my daughter in both the short and long term.  During that time, I read the book by Liz Perle called Money, A Memoir and it helped me think through how I was going to handle money in the future.

We reside in lovely San Diego, CA.  It’s a good life here for a lot of reasons including the wonderfully temperate climate.  I grew up on the east coast in CT, went to a liberal arts college in the southeast, graduate school in TX (MBA) and eventually worked my way to San Diego, a place I always dreamed of living.


Besides being a financial nerd, I have a lot of hobbies with a recurring theme of physical activity.  I have dabbled in triathlons of different distances (even did a half ironman distance race in late 2012), tried to master 5Ks, I have run a few marathons and 10ish half marathons (not sure my marathon pace truly qualifies as running), I snowboard as much as possible in the winter, and currently I am focused on my Bikram yoga practice and trying to unravel my overly tight muscles from years of hard physical activity coupled with nearly two decades of sitting too much while working.  Oh,  I love traveling and growing vegetables in the small patch of garden we have!  I’m someone who loves adventure and living slightly outside my comfort zone.

I work on the business development side of the house for a privately held bank specializing in commercial owner-user real estate transactions for small businesses.  I also have a leadership role in my company and manage a team of 5 other folks.  Some companies call that being a player-coach.  I call it having two jobs both of which are rewarding in their own way.

In less than 30 days, I will be officially “early retired”.  I gave notice more than a year ago and my departure date from corporate America is June 30, 2017.  I’m about to enter an exciting new chapter of life.

Let’s get some details – how much money do you make, and how long did it take you to get there? And are you a millionaire or are you on the way?

I’m in a commissioned sales type position so my salary varies widely.  It “depends” on so many things – the general economy, how hard I want to work (though sometimes I’ve worked super hard and not done well), the financial institution for which I was working, interest rates and a little bit of luck.  I have a smallish base salary, so truth be told, it’s easy to stay motivated when making ends meet on your base salary would be difficult.

In general, over the 15 years I’ve been in this position, I’ve averaged between $250,000-$350,000 in gross income on an annual basis though I made less than 6 figures in 2008 during the recession and barely made over that in 2009.  I know that is a wide range, but it swings that much!  After state and federal taxes, those numbers are less exciting than they look on paper.

I don’t count my home value in my net worth – since it is just a pure expense to me and doesn’t generate any passive income to help me as I enter my financial independence phase of life.  I have a small mortgage on it which is about 40% of the original purchase price, for those of you who like the details.  It was only part of my FI calculation in terms of what my budgeted costs of home ownership are.  When I last updated my spreadsheet at the end of the quarter, I have $1.5 million in assets earning me a living while I mostly sit back and twiddle my thumbs.  Of course I fully expect that number to drop during our next recession which is why I have lots of cushion built into my FI budget.

How did you get started in the workforce?

I didn’t jump right into having a serious banking job right away.  I spent my first 3 years after undergrad coaching college soccer, 2 of which were spent as a graduate assistant coach while pursuing my MBA, though I had no idea where I would go with that.  I got hired by a large publicly traded bank’s middle market group upon graduating from my Master’s program and frankly didn’t have a lot of other job prospects.

I somehow managed to land a job right away.  Through grassroots soccer work I had done in my community, I got to know several of the senior folks in that banking group, and I got hired.  I think that’s been a theme throughout my career – I didn’t quite know what I wanted to do but I had to do something and when an opportunity presented itself and felt like the right thing, I went for it.


How did you get from where you started to where you are now?

Essentially I spent my first 5 years in banking working for a large publicly traded company, received a lot of great training but was quite bored.  I was hired concurrent with two large banks merging and was transferred from my smallish city in TX to Dallas, TX after 1 year, and 6 months later to San Diego (my dream city!!!).  Of course, I jumped on that opportunity but the corporate culture from which I came functioned as a meritocracy where hard work was rewarded and appreciated, efficiency was celebrated and a clear career path presented itself.  I moved to a market that was from the other side of the merger and it was quite different.  People were career bankers and it was less of a team environment and more about seniority and there was no clear path to advance.  Further, there was no benefit for efficient work habits.  Because of the seniority culture, I was expected to show up first and leave last and spend 12 hours a day at the office regardless of having only 4-5 hours of work to do.  As a highly self-motivated and disciplined person, that type of work environment thoroughly crushed my spirit.

A few years later, I left a prestigious job title at said mega bank, took 30% cut in my base salary and took a business development position.  I was my own boss and in charge of my own destiny, in effect.  I got to work from home (I had several friends who did that – and I was jealous of them!) and I started off on a path that would lead me to FI.  I didn’t have any huge expectations, I just figured that I would do as well as I was doing already with less structure and I would benefit from efficient and disciplined work habits.  If I failed, I could go back to the other job role.  A couple years later, I moved onto what I felt was my dream job for a cool and entrepreneurial company however, when the financial markets imploded in 2007, that company went bankrupt and I moved to a business development position in a large publicly traded lending institution.  I spent a couple of years there but it was hard to get any business done so I took a larger risk than the first time and took a 42% cut in my base salary to move over the smaller, privately held bank where I am still employed.  That risk was scarier than the first because at this point I was the single mom of a toddler and all the hard work and saving I had done for the past 5 plus years seemed worthless when the stock market imploded.  Nearly 8 years later, I have hit the pinnacle of my career.


Where do you want to go in your career – and your financial life?

This is an easy answer.  I hit my FI goal over a year ago and once I hit my goal number, I spent a little time sorting out my exit strategy and discussed my plans with the CEO of my company.  I accomplished more than I ever set out to do and I feel like I’m ending on a high note with my career completely at peace with my decision.

I’m excited about where my non-career life will go!

What’s the biggest challenge in being a breadwinning mom? What’s the best part?

Biggest challenge – it is hard to fill all the roles I feel like I need to fill well. I have mommy guilt in that I don’t have the time to volunteer at my daughter’s school on a regular basis.  It’s challenging having such demands on my time.  Best part – I don’t remember the last time I was stressed about money.  Even in my darkest days when I was a single mom, going through a divorce and I was suddenly making less than 1/3 of what I was making previously, I wasn’t stressed about money.  I had saved a lot when times were good and my lifestyle design allowed me to live within that amount of income (and still max out my 401K!).  Admittedly, watching my investments decline more and more every month as the recession took hold made me wish for a short time that I had spent more of that money.  It was foolish but I experienced firsthand those intense emotions that go along with the stock market dips and it was a great lesson.  I view the big dips as opportunity now!

Becoming a millionaire is a dream of many people. How did you get there?

Honestly, being a “millionaire” was never a dream of mine.  It was never about the money.  I wanted a job that gave me the freedom to define my own success, work on my own schedule, and one where I was objectively measured.  Getting paid incredibly well to have all those other important things was icing on the cake.  Of course the downside to that freedom is that I’m always working and always connected but that structural freedom was super important to me.

What do you see as the key to earning such a high salary?

For me, the key was having a job where I was objectively measured.  Before I was in a sales type position, I didn’t know how to advocate for myself and negotiate raises.  With those objective type of measures, I felt very confident about walking into my boss’ office and demanding that I get a base salary the same as the other highest producer in my company at the time (true story).  There is something empowering about the objectivity.   Like many women, I had a bad case of imposter syndrome for a lot of years and after consistent high-level performance,

I finally began to feel very confident, embrace and understand the things I did that made me successful.  In general, it’s such a cliché, but I’ve never been afraid of hard work.  I’ve never been afraid of a challenge and I always seek to add value in whatever role I’ve filled over the years.  Also, I never worried about the money part of it.  I’m in sales and it can be a real grind at times but when I first started I had a long-term plan in mind and figured that doing sales was like working out, I had to build a good foundation and, every day, exercise the behaviors that would bring me business.  Every few months, I needed to re-evaluate and tweak the “business model”, but I knew if I committed to the daily discipline of it, it would work in the long run.  And it has.

Have you ever experienced issues in the workforce because you’re a woman? What did you do in response?

This is a loaded question!  Yes.  I don’t know very many women who haven’t experienced “issues in the workforce.”  I’ve heard men talk about women in objectifying and sexual ways, I’ve had bosses grab me in inappropriate ways, and I’ve experienced countless micro-aggressive type behaviors over the years.  In my younger years, I kept my mouth shut and quickly learned how to avoid situations where unsavory groping might occur.  This specific type of behavior was relegated to my time at the very large publicly traded bank, for the record.  I wish I’d had the courage to speak up but fear kept me from doing so.  As I grew older and more confident in my position and my career, I have had more courage and I haven’t been afraid to call people out for their objectifying language and behaviors though I haven’t witnessed anything as ridiculous as early in my career.  I hope the workforce is friendlier to women now than it was 20 years ago.  I’m not sure that it’s any different, however.

Also, I had a lack of mentors and role models who are women.  I’ve been lucky to have a couple of women influence me in positive ways but I wish there were more women from whom I could have learned.  I hope as the workforce shifts to having more women in leadership positions, younger women will have more opportunities this way.


Chief Mom Officer is primarily a personal finance blog – tell us about your saving and investment strategy

I wouldn’t say personal finance is a “hobby” of mine.  It’s a necessity and like most people, I didn’t have anybody teaching me about it.  I just decided to read and learn so I could understand what to do with my money.  I took economics, accounting, and finance classes with my MBA but there was no focus on personal finance.  As an aside, I wish that more MBA programs would have classes on things like the Trinity Study and John Bogle’s brilliance with designing index funds.  I might have been a better “life hacker” and retired 10 years ago if I had learned more about these topics.  I always intuitively understood that mastering your own money can bring you freedom and so it was natural to learn as much as I could about it.

Big financial goals – I’ve met all of them.  Now I get to see if the investment strategy I have employed will work.  In some ways, this is the hard part, sitting back and waiting.  My strategy is likely not that much different than other FIRE folks.  Let’s assume that everybody knows to live well below their means and to stay away from consumer or automobile debt.  From that point, my strategy is:

1) Max out your 401K,

2) stash away as much after tax money as possible in index funds

  •  I have money in Vanguard in 4 main categories – US index fund, international index fund, us bond fund, and an international bond fund.
  • I also like Betterment as an investment vehicle.  I realize there are some costs to it, but there is an efficiency and elegance to it that I dig.  After a couple of years, I’ll be curious if my returns are better than my marginally lower cost Vanguard mutual funds due to the automation and tax loss harvesting imbedded in the Betterment platform.

3) Finally, I have a stash of money in some alternative investments which theoretically aren’t correlated with the stock market, but I will see if that is true or not when the recession comes around.  I lend money via the peer-to-peer lending site called Peer Street.  Note that these are 1st trust deed secured real estate investments, not unsecured consumer loans like LendingClub.   I have been investing with Peer Street since August 2015, but MMM did a blog post on the company last April if folks are curious.

I view Peer Street as similar to investing in REITs but instead of a pool of investments chosen by the REIT fund managers, I get to pick and choose which real estate project I want to fund by seeing the granular details.  As a career banker, this type of investing appeals to me.  At this point, my entire Peer Street investment is structured almost like a CD ladder (albeit with much higher returns), a few loans are always paying off every month and I’m re-investing my earnings and the loan payoffs in new loans being offered on the site after I go through my personal due diligence checklist on each of the choices.  When I retire, having this kind of access to cash flow with the only taxable event being the interest income received seems like a good idea and should allow me to manage my tax liability.

Real Estate – I currently only own the house in which I reside.  I used to own a rental condo but it was a lot of work and a lot of stress and I didn’t achieve the kinds of returns I receive in less labor-intensive investments nor do I have the threat of any potential lawsuits.  I think it’s a valid way to pull off FI, just not part of my strategy.  I don’t think I have the intestinal fortitude for them.

CMO Note – Wish I Could Surf wrote me later to request that I mention she also has a significant college fund for her daughter – $60k set aside in a 529 right now. 

What’s the top three pieces of advice you’d have for someone just starting out in the workforce, struggling with their career, or just looking to improve how they handle their money?

Starting out

  • It’s ok if you “don’t know what you want to do.” I honestly had no idea what I wanted to do for a living even after being a banker for 3 or 4 years.  I was more clear on how I wanted to integrate my job into my life.  My career has been incredibly rewarding and fulfilling and I’ve helped drive the economy on a micro-economic level while at the same time building wealth for entrepreneurs.  But I had no idea that it would lead me where it did.  I didn’t start out having any sort of defined ambition or goals and maybe that lack of pressure and definitions made things a lot easier.
  • Be flexible. That’s been a key to my success long term.  I was able to jump on an opportunity to move to Dallas and San Diego 6 months later because I decided to just roll with things and see where they took me.  Had I not moved to San Diego, I might have stayed on the well-defined career path I was following previously.  I didn’t like the job structure I had so I changed to something that would work for me.
  • Take risks – design your life and finances so that you can pursue your career on your own terms. This way, there is room to take some calculated risks.

Struggling with career

  • Think long and hard about what is important to you. The last few years at the large publicly traded bank, I felt a sense of dread and misery with my job, but I paid attention to what other people did for a living and how their job was designed and figured out how I wanted to work and how the freedom was more important to me than any fancy office or job title and frankly, I hated wearing a fancy outfit every day.  Now I dress up when I see clients or travel to my corporate offices, but otherwise no one cares that I am wearing yoga pants or soccer shorts and a ratty t’shirt while I work.
  • Even if you are struggling, be patient and bide your time, as I think it’s always easier to get a new job if you already have a job. It gives you more negotiating power as well.
  • Finally, look at your struggle and figure out if there is something that you can change about yourself. I was struggling with burnout a few years ago, but I spent some time identifying what things made me feel burned out and totally overhauled my approach, minimized or eliminated the parts of my job that made me feel burned out and I had the best two years of my entire career (in terms of monetary compensation).

Improve how to handle your money

  • To some people and many women, money is a taboo topic. I think it’s important as women to discuss money the same way men do.  There are studies that show that part of the reason why women aren’t as paid as well as men is that we don’t talk about money.  It’s so secretive and taboo that we don’t know what other people in the same position and skill set are paid, so we are unable to negotiate with as much knowledge as our male counterparts.  Also, I think us women have a harder time asking for more because it may seem arrogant or egotistical.  Remember that self-confidence and ego are different.  The more we talk about money (or anything for that matter) the more control we have.  That book by Liz Perle I mentioned in the beginning is a great place to start even if you haven’t been through a divorce.
  • If you have a partner, make sure you and your partner are open and honest about finances. You don’t have to be on the same path, but you must be on the same page.  I see old and young couples who “hide” and lie to each other about expenditures and habits.  It makes me cringe when I hear those things.  Don’t let your partner control everything nor should you control everything.  My partner and I run our finances separately and while we are accountable to each other, we don’t have to “get permission” from the other on what we buy or how we invest.  We both spend mindfully and are index fund investors, and while we have separate finances and follow slightly different paths, we have the same long term plans and goals.  We met later in life and the assets I brought into the relationship were different than what he brought but we were open and honest and had grown up conversations about it and put together a fair arrangement on how we would handle household expenses.  Recently, I listened to a Podcast from the Mad Fientist where he interviewed his spouse and they run their finances separately too!  Here’s a link to that.
  • Remember that buying a new car or new clothes only gives you a quick short term dopamine rush and doesn’t bring long term happiness. I love going out to eat as much as anybody else, but I understand the impact of these expenses on my financial well-being (and health).  Be mindful about your spending and try to take a long-term view so you understand what tradeoffs you are making if you have a $200/month manicure habit and $500/month clothing habit, or a taste and/or desire to hoard expensive shoes.  Multiply monthly expenses by 173 to see the real impacts of some of the habits you have over a 10-year period.  Ask yourself if these expenses align with your own long term goals and values and if they are worth putting off financial independence indefinitely.  You don’t have to cut those expenses out completely but think outside the box.  You can find nice, high-end, used professional clothes and shoes on or other places like consignment or thrift stores.  You can cut back your restaurant and bar habits but still be social by organizing potlucks with friends or cocktail and appetizer hours with friends at their homes and apartments.

Again MMM wrote article a while ago, and it neatly defines the impact of those weekly and monthly expenses.  I

I feel like I live a life of luxury but when I drill down, I can support both myself and my daughter on $4,000 or less a month (I subsidize travel with travel hacking) even in super expensive Southern California, with a mortgage payment.  I’m mindful of where my money goes but I don’t feel frugal at all – I don’t even like the word as some people equate frugal with being cheap.  For you details people, my estimated income tax burden is built into that $4,000/month budget.

Where can people connect with you?

I am happy to respond to comments, but since I’m still working, I don’t want to reveal my full identity or email.  Moreover, I’d like to slide quietly into retirement and break my computer and phone habit/addiction.  I have a pretty minimal social media presence anyway.  🙂

CMO Here Again

Thanks so much to Wish I Could Surf for stopping by to share her story! Similar to Mama Fish, and Temple BoClair, she succeeded in a traditionally male-dominated field. Now she’s preparing for early retirement – amazing! Be sure to leave her a comment below – and share this post to help inspire other women in the same situation!

Want to connect with other money smart women? Join in my Breadwinning Women or Women on FIRE Facebook Groups and find other money smart women like yourself.

If you haven’t already, be sure to swing by my one-stop shop page for Breadwinning moms, featuring all my prior articles and interviews (plus some updates on prior interviewees!). Know someone that would be perfect for this series, or is that you? Hop over to my “Be Featured!” page to access the request form.

Be sure to follow my blog for more great posts via e-mail or WordPress, or connect with me on Facebook or Twitter and say hello! You can also check out what I’m buying or baking on Instagram,  what I’m pinning on Pinterest, or the latest books I’m reading (or want to read) over on Goodreads.

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8 thoughts on “Six Figure, Breadwinning, Millionaire Moms – Wish I Could Surf”

  1. That’s a great story. And with a divorce thrown in there too. In thinking back, my divorce really motivated me to take charge in life too and make sure that I could “make it” without anyone else. Divorce drowns most couples… Congratulations on all your success! Try not to let the mom guilt get to you. I had trouble getting to some of my kids events (and I worked in a school!) The love and stability you give them as they grow up is a lot more important than a soccer game or a 2nd grade field trip.

    1. Thank you! Though my divorce was devastating in a lot of ways, I am grateful that we kept our daughter’s well being in front of whatever drama and anger the two of us felt. Financially, it was a pretty rough setback but it was the kick in the butt I needed to take complete control of my finances, fire my financial planner and define my goals. I don’t have a lot of guilt but it hits now and again and I don’t tend to dwell on it.

  2. The Green Swan

    What a great story, thanks so much for sharing! While a male, I can relate to so much of what you described in banking careers, challenges with mergers, the recession etc. It’s inspiring to hear how you’ve hit FI and are ready relax a bit and reduce stress. I’ve found that it can be rewarding but very stressful and one of the reasons I’m looking forward to early retirement as well.

    1. I will say working for a smaller privately held bank removes a lot of the layers of management and provides less opportunity for competing agendas. In a 20 year banking career, somehow I escaped several rounds of layoffs unscathed and managed to jump ship in early 2008 while I still had negotiating power before my company completely fell apart. Working from home for a good chunk of my career has also made things more tolerable as I don’t have to deal with any of the workplace tension or drama. Thanks for the positive feedback.

  3. Phenomenal story! I am loving all your featurettes! And as a blogger I notice how much more exciting CMO’s questions are then say the generic Q&As on TV.

    I wouldn’t count my home into net worth either but since we are generating a lot of income as a partial rental, I cut myself some slack teehee.

    Mommy guilt is a big issue for women who have careers and it’s something I feel even too even though I have no children. If my husband comes home and I’m just as tired as he is, we end up both zombied out on the sofa. I feel a little bad that I can’t be more energetic to cheer him up. It’s called wifey guilt I guess?

  4. I would probably count part, if not all, of my home equity as an asset if it were generating any income! The guilt hits sometimes but I don’t tend to dwell on it. I don’t feel it much with my husband, lol. I only put pressure on myself when I feel like the balance of all the other stuff we have to do is out of whack and I’m not doing my fair share. Thanks for the positive feedback. I’m not sure what you are referring to as featurettes, but those would be CMO’s doing and not mine at all if you are referring to the pics. She is the creative one!

  5. Another inspiring glimpse into the lives of women who rocked it in business and life! Awesome and I hope retirement is just as fulfilling for you wishicouldsurf! Enjoy that extra time with your daughter.

    1. Thank you very much! I am looking forward to the extra time though I’m realistic that there is sure to be a little tension. I’m still figuring out how to rock it in life, but felt like I crushed it in the business category. 🙂

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