Fearless Conversations Can Help You Grow Your Money – and Your Relationships Too
Get over your discomfort, because even though talking about finances can be awkward, it’s worth it in so many ways.
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Let’s face it. Talking about money is not one of those conversations most people look forward to. Everyone has different opinions about money: How it’s used, how much you need, how much you should save, how much you should spend. The list is truly endless.
Knowing that money is a hot topic, it’s a subject that many avoid. That’s a huge mistake. There are so many benefits to having fearless conversations about money. At our firm, we prioritize discussing these difficult, potentially sensitive questions with our clients. We want to get at what truly matters to them and gain a clear idea of their financial situation. This helps ensure that their money is best aligned with their goals.
These kinds of conversations can benefit anyone. I’ll focus on several of the biggest payoffs.

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Start with a heart-to-heart with yourself
We’ve all heard the saying that “knowledge is power.” Start gaining knowledge by having a fearless conversation with yourself by digging in and exploring your own personal relationship with money.
All of us were taught things about money as kids. You might have picked up bad habits from the adults in your life who spent beyond their means, didn’t save, and racked up credit card debt. Conversely, “good habits” – like saving aggressively and not spending – sound good in theory, but not if there’s only work and no enjoyment. A solid balance of saving and spending is the healthy way to go.
It’s important to understand what your “money story” is. You carry that into your life and relationships with others virtually every day. Whether you speak to a financial therapist or process your habits with regular journaling and introspection, try to understand what your money habits are and where they may come from. Once you have that personal understanding, it’s easier to take on the challenge of seeking out new answers and knowledge from the financial industry. As you take on difficult topics and gain understanding of markets and investments, your net worth should ultimately see gains as well.
And with that fearless introspective conversation, it’s important to remember to pass along your knowledge to your kids to help create generational wealth. While it may not be easy at first, finding ways to discuss healthy money habits with your kids regularly will help them thrive later on. Your money story influences not only you, but your children as well, so be fearless in how you want to write the next chapter.
Ask for – and get – that raise
One fearless conversation that many people find daunting – and who doesn’t? – is asking for a raise. In a recent survey conducted by payscale.com, just 37% of workers reported asking for one. (opens in new tab) Since most companies don’t conduct regular compensation reviews, this number is astonishing.
If you’re not regularly discussing compensation with your employer once a year, that should change. This doesn’t mean you should necessarily get an annual raise, but you should understand where you stand, where your employers are getting their data, and what it will take to see an increase in your compensation.
Looking out for your own personal success is imperative to living your very best financial life. If you don’t take on this conversation, chances are, it won’t happen. According to payscale.com, just 30% reported getting a raise without asking for it.
Create a solid groundwork for great relationships
We all know that money issues are often implicated when marriages fail. For prospective couples, not sharing their perspectives on money early in their relationships can be a big contributing factor.
Getting married or starting a relationship is one of the top arguments – in my humble opinion – for having those fearless conversations. Understanding your partner’s view of financial security and success is imperative to the success of the relationship. Both partners should understand how the other thinks about debt, spending, budgeting, credit ... it can be an exhaustive list.
If you disagree on any key issue, you need to plan – yes, fearlessly – on how you’ll address this together before you get too far down the road to forever. There is no one-size-fits-all solution. But candid conversations with your spouse or significant other about all things financial will help to uncover any skeletons before they turn into a crisis.
These kinds of talks can also clear the air with friends who spend a lot more than you do on trips and restaurants. It can be awkward and uncomfortable to say when the price is too steep to join in. But what are true friendships about anyhow?
Make big life transitions easier – with fewer unwanted surprises
Fearless conversations about money can happen with your parents too. I know this may feel weird, but if you haven’t already done so, talk with your parents now about their plans for the future and as they get older.
Gaining a solid understanding of how they want their life transitions to happen while they’re healthy, you can partner with them to ensure these goals are realized as they had hoped and planned. Importantly, this might include working with them to sort through their estate plan.
If you want to explore these ideas further, check out my previous article on Kiplinger: Yes, Our Parents Are Aging, But We Can Help.
Enjoy more meaningful connections with the people you care about
Ultimately, having fearless conversations with those you love can deepen your sense of connection. You may also find that this ability to discuss what was formerly taboo can open up all sorts of avenues. Whether the topic is money or commitments or chores, clearing the air and developing understandings with friends and family can make all the difference.
Life throws us curveballs, constantly forcing us to reassess our goals. If you’re willing to put in the effort, energy and time, you’ll reap the rewards. Fearless conversations are never easy, but they get easier as you get more experience with them.
Kelli Kiemle is the Managing Director of Growth and Client Experience at Halbert Hargrove (opens in new tab) and has been with the firm since 2007. Kelli earned her Bachelor of Science degree in Business Administration-Business Communication/Marketing from the Marshall School of Business at the University of Southern California in 2006.
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