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20+ Personal Finance Experts Answer: What is the biggest money obstacle you have overcome?

Last year I was very fortunate to interview some of the best and brightest personal finance bloggers out there in the blogosphere. One of the questions was “What’s the biggest money obstacle you have overcome?”

No matter which of these stories you can relate to it’s important to remember that we all have money obstacles to overcome.  So if your money goals are feeling a little harder than they did on January 1st, know that you aren’t alone.

Hitting your goals takes time, but as you will read they are totally worth it.

If you would like to be included in future round-ups send me a message about being featured on our Behind the Screen Interview Series.

What is the BIGGEST money obstacle you have overcome?

In total, I borrowed $81,000 in student loans. Paying off that amount was the hardest thing I ever did. It tested me in ways I couldn’t imagine. I gave up everything I thought I knew about money. I did jobs I never thought I’d do. I hustled harder than anything, which really did prepare me for self-employment. I gave up what I thought I “deserved” and lived very minimally, on next to nothing.

Paying off debt isn’t easy and it was by far the hardest money obstacle I have overcome.

How has overcoming that obstacle changed you?

I’m a changed person now that I’m debt-free. I set bigger goals. I view money differently. Paying off debt has also increased my confidence and shown me what I’m really capable of. I’m unstoppable now! (ha, just kidding)

Check you the full interview here

Grab her book Dear Debt here

Life Impacting book: Your Money or Your Life by Joe Dominguez

Melanie

Dear Debt

What is the BIGGEST money obstacle you have overcome?

For many years, perpetual consumer debt was our biggest money obstacle. Paying off the student loans was simple because when we were done, we were done – there was no desire to buy more college degrees. But when we paid off auto loans, even though we had all good intentions of saving more, it was never long before we financed our next new(ish) car.

Thankfully, we remained frugal with almost everything else throughout our truck and car purchasing years by keeping food, clothing and other expenses to a minimum. And we have since changed our ways and become consumer debt free (still have a mortgage).

How has overcoming that obstacle changed you?

Flash forward a few years. We’ve had the same vehicles for several years now and plan to drive them until they are no longer roadworthy.

I don’t know what exactly changed me, whether it was the debt epiphany or the new desire for FI, but in the time span since we made the decision to stop the debt cycle, I’ve completely let go of any cares about what other people think of me. I have zero desire to live like the Joneses.

Check out the full interview here

Life Impacting book: Your Money or Your Life by Joe Dominguez

Amanda

Centsibly Rich

What is the BIGGEST money obstacle you have overcome?

Learning to live within my means. It sounds silly to say this, but it never occurred to me that life without debt was possible – or that debt meant I was living beyond my means.

I assumed that going to college meant you had student loans, driving a car meant you had a car payment, and if you wanted to buy things – anything – you did it with credit. My world was turned upside-down when I discovered there was another way.

How has overcoming that obstacle changed you?

Learning to live within my means has changed everything for me! All my financial decisions are made from that perspective and as a result, I make completely different decisions than I would if debt was an option.

My sense of contentment and sense of gratitude have increased and are continually challenged – which I think is a good thing.

Check out the full interview here.

Life impacting book: The Total Money Makeover by Dave Ramsey

Alaya

Hope+Cents

What is the BIGGEST money obstacle you have overcome?

I’d say there’s two big ones for me (and probably a million little ones). One is budgeting and/or tracking my spending, and the other is comparing my own financial situation to other people’s situations.

I was perfectly happy for a long time having no idea what I was spending…Once I started actually tracking my spending, I realized I was spending money on things that didn’t have any real value to me, and it was painful seeing the numbers in front of me. It was a realization of how much money I could have had at that moment, if I hadn’t been throwing it away so easily.

The second one started out of an innocent desire to find out what was “normal” for finances at my age. I didn’t know how far behind I was, so I thought it would motivate me to know where my peers were with their money.

It took me a while to figure out that there is no real “normal” and that since everyone’s lives and circumstances are different, their financial pictures would be very different too.

How has overcoming that obstacle changed you?

Have you seen the movie Face-Off? That’s me. I went from being the Nicholas Cage to the John Travolta of my own personal finance. (Because in the movie Nic Cage is the bad guy and becomes the good guy. And also because in real life Nic Cage apparently sucks at money.)

Point is, huge change. I spend far less money on things that I don’t value and I’m actually a lot happier with the things I do have.

Check out the full interview here

Life impacting book: The Wealthy Barber Returns

Kate

Kate Saves




“I’m a changed person now that I’m debt-free. I set bigger goals. I view money differently. Paying off debt has also increased my confidence and shown me what I’m really capable of”

Melanie -Dear Debt

What is the BIGGEST money obstacle you have overcome?

It would probably be living within my means. I spent far too much money on things I didn’t need when I was younger. I was fresh in college and lived on my own, and thought I “deserved” a lot of things. I didn’t think about my future, and that led to a lot of wasteful spending!

How has overcoming that obstacle changed you?

It has definitely changed me. It made me realize that material things are not needed. I now make $70,000 a month and I spend far less than I did when I was struggling. It’s interesting how that has turned out.

Check out the full interview.

Michelle

Making Sense of Cents

What is the BIGGEST money obstacle you have overcome?

Leaving my savings account alone has always been tough, so I’d say that learning to be disciplined enough to keep my greedy little hands off the stash has my biggest money obstacle.

I was always pretty good at starting to save money, but as soon as that money began to add up the temptation to spend it would become too much.

It wasn’t until I realized that financial independence and early retirement were real possibilities that I was able to overcome this obstacle. Rather than using my money to buy stuff, I could now using it to buy my freedom – that’s when my lightbulb went off, and that’s when everything changed.

How has overcoming that obstacle changed you?

Learning how to leave my savings alone is what finally put me on the path to Getting Rich Quick’ish! The formula for creating wealth is so simple, and it all begins with saving:

  1. Spend less than you earn (i.e. save some money!)
  2. Invest the difference
  3. Eliminate, then avoid debt

Realizing that I was buying my freedom changed everything. I became a man on a mission and was constantly looking for ways to save more money, for expenses to cut, ways to contribute more to our 401k, etc.

Check out the full interview here.

Life impacting book:  Dear Debt

Ty

Get Rich Quickish

What is the BIGGEST money obstacle you have overcome?

Probably getting out from under that house. We lived in it for a solid 5-6 years and then wanted to dump it, but it was too underwater so we were forced to become landlords while we rented elsewhere. It worked out semi-decently for a few years, but then the renter had to skip town on military orders and we had to make the call of selling it in the middle of winter or renting it back out… We decided to go for it, and 45 days later with $20,000 more sunk into it, it was sold and make me the happiest guy around 🙂
Never again will I do something just because people say “it’s smart.”

How has overcoming that obstacle changed you?

As annoying as it was, picking up that house completely changed my life. Without buying it I wouldn’t have stumbled across finance blogs, learned about a career I had never heard of before, met a TON of new and awesome like-minded people, or become self-employed and learned all about entrepreneurship. So it was pretty much the worst, and the best, decision I could have made 🙂
J Money

Budgets Are Sexy

What is the BIGGEST money obstacle you have overcome?

I had some student loan debt coming out of medical school, but it wasn’t insurmountable, especially on an anesthesiologist’s salary.

There’s no way to say this without invoking the world’s smallest violin #firstworldproblems (shut the full cup), but it’s probably learning not to hoard money. I need to be better about not sweating the small stuff and realize it’s alright to splurge a little sometimes. I’m better at spending on others than I am spending on myself.

How has overcoming that obstacle changed you?

I’m still tripping over hurdles, but I would say the biggest change is that I realized I don’t need to work until I’ve built an eight figure net worth. I have no idea what I would do with all that money. It might be cool to have my name on a building or something, but I’d rather have my freedom in my forties than a hand on a golden shovel in my seventies.

Check out the full interview here.

Life impacting book:  The Only Investment Guide You’ll Ever Need by Andrew Tobias

P.O.F.

Physician On Fire

What is the BIGGEST money obstacle you have overcome?

Garrett: Eliminating the mindset that debt is okay.  

Claudia: Convenience!  When everything is a drive-through, it makes convenience food too easy to consume (and waste a ton of cash on).  Learning how to plan meals was definitely a huge obstacle for us.

How has overcoming that obstacle changed you?


Garrett:  By mentally saying “debt = bad,” we started to question all purchases, began to figure out ways to eliminate debts and ways to earn/save additional money to eliminate the debt we had.  This paradigm shift resulted in us questioning the 30-year mortgage we had on the big house.  Since debt=bad, we decided to eliminate our largest debt: the big house.  We downsized from a 1,500 sq feet to a 536 sq feet house.  This one step had a chain reaction of positivity.  We’ve reduced debt from $240,000 to about $56,000 today.  We have reduced our stress levels and improved our health.  We have also found that we have tons more time to do the things we want to do rather than mow a big yard, remodel, or clean a big house.

Claudia: Honestly, we have not 100% tackled our grocery budget, but I’d say we’re 90% of the way there.  Overcoming (much of) the obstacle of convenience has changed us in several ways.  Now that we don’t eat at restaurants or get fast food as much, we’ve lost weight, paid off tons of debt, and we have a lot more energy.

Check out the interview here.

Life impacting books:

Garrett: Cashflow Quadrant

Claudia: Think and Grow Rich!

Two Cup House

Two Cup House

What is the BIGGEST money obstacle you have overcome?

My hubby and I are both buried in student loan debt – together, we started with a grand total of $117,000. We are currently down to $80,000.

We had a lot of expectations about what our lives would look like after finishing school, and we had to make changes to our plans. We had to accept the fact that our life is going to be very different from how we imagined it.

How has overcoming that obstacle changed you?

My hubby and I have learned to stop caring what other people think and to stop doing things just because those things are “normal.” “Normal” in the U.S. means having multiple forms of debt – credit cards, mortgages, student loans, car loans, etc. We don’t want to be “normal” anymore. A lot of people think that we’re crazy for living with my parents and being so frugal, but it’ll be worth it when we’re debt-free.

Check out full interview here.

Life impacting book: The Total Money Makeover by Dave Ramsey.

Jen

Frugal Millennial

What is the BIGGEST money obstacle you have overcome?

Negotiating. I have a hard time speaking up, and for years, I undervalued my work. It’s hard to just say, “hey, I’d like more money,” you know? Of course, that’s not how you ask, but that’s what negotiating feels like when you’re afraid of it. However, a few years ago, I forced myself to start asking for more, and I was amazed at how effective it was. I still struggle with it, to be honest, but it’s getting easier.

How has overcoming that obstacle changed you?

For one, I earn more money, which is awesome. More importantly, though, I feel more powerful and in control of my career, and that confidence is invaluable.

Check out the full interview.

Life impacting book: Dave Ramsey’s Total Money Makeover

Kristin

The Wild Wong

What is the BIGGEST money obstacle you have overcome?

Probably adjusting to life after university on my new-grad salary!

Of all the things I wish someone had told me as a new grad, the biggest one is that your salary doesn’t have to be your only source of income. It was such a rough adjustment, trying to make everything fit into a set monthly amount, in addition to being fully out on my own for the first time. If I had built a side hustle, that extra income – no matter how small! – would have been unbelievably helpful.

How has overcoming that obstacle changed you?

I will say, it made me really committed to living within my means! I figure if I can stay away from the Credit Card Debt Monster on a new grad salary, there is just no excuse under the sun to ever get into it now, on a much more comfortable salary with a few years’ experience.

It also prompted me to start making the kind of resources that I wish I had back then, like my One-Minute Budget spreadsheet. If anyone had told me about how to break down a budget by percentages, it would have given me a much more balanced look at my money – instead of just the “save as much as you humanly can” approach I took!

Check out the full interview here.

Life impacting book:  The Wealthy Barber

Des

Half Banked

“I used to be in a hurry practically all the time, but now, I realize that rushing through life is no way to live. I’ve learned to slow down. I’ve learned how to enjoy life’s little moments as they happen. I appreciate the little things a lot more.”

Steve – Think Save Retire

What is the BIGGEST money obstacle you have overcome?

Honestly, no obstacle was all that difficult to overcome. This is a mindset issue, not a money issue. Once we set our minds to early retirement, no obstacle was all that tough. It just takes some time, that’s all. If anything, it’s TIME that’s been the biggest challenge. We hate waiting.

How has overcoming that obstacle changed you?

I have become a much more patient person over the last couple of years. I used to be in a hurry practically all the time, but now, I realize that rushing through life is no way to live. I’ve learned to slow down. I’ve learned how to enjoy life’s little moments as they happen. I appreciate the little things a lot more.

Check out the full interview here.

Life impacting book:  The Millionaire Next Door

Steve

Think Save Retire

The biggest obstacle for me has absolutely been cutting back on some social outings I would normally jump at. One of my closest circles of friends loves to go out every single weekend to experience a new restaurant, nightclub, or event. I unfortunately had to start saying no and change a bit of my hobbies. It’s actually been the best thing that’s ever happened to me.

How has overcoming that obstacle changed you?

It 100% has changed me. I no longer feel the need to let FOMO get to me, and I now live a healthier and more enriched life. I have things that I love and inspire me. I think it helped me find my passions.

Check out the full interview here.

Life impacting book:  Million Dollar Women

Alyssa

Mixed Up Money

What is the BIGGEST money obstacle you have overcome?

Among the many financial obstacles that my wife and I have encountered, student loan debt was the biggest – by far! My wife was fortunate to graduate school without any student loan debt, as her parents had the means to pay her tuition. On the other hand, despite a full-tuition scholarship, I had to take out student loans to pay for room and board and miscellaneous living expenses. Fortunately, since getting married in 2010, we had been making strong headway on my undergrad loans for quite some time and had been nearing the light at the end of the tunnel.

Then I decided to go back to school for my Masters degree in School Leadership. And then we decided to buy a house.

In the fall of 2015, we finished paying off my undergrad loans, and after the hustle of Christmas, I had a quarter-life crisis (I fully plan to live to be 120!) when I realized that we still owed nearly $18,000 on my grad school loans. For the next 54 days, we went nuts, and on May 13, 2016, we made our final payment on my grad school loans, then looked up and realized that we had paid off $17,831.65 in just 54 days. You can read the full story here (http://www.financesuperhero.com/kicking-sallie-mae-to-the-curb-goodbye-student-loans/).

How has overcoming that obstacle changed you?

Freeing ourselves from the shackles of student loan debt has been incredibly freeing. In the process, we learned the value of taking action to initiate change. We also experienced the rich rewards of sacrifice. It was also extremely gratifying to work together and accomplish a goal faster than we thought was possible.

Check out the full interview here.

David

Finance Superhero

What is the BIGGEST money obstacle you have overcome?

The biggest money obstacle I had to overcome was taking control of my own finances. I was very doubtful and worried about managing my own money in the beginning. I think the hardest thing about it is if you make a mistake you know exactly who is to blame. But in doing this I learned a lot

How has overcoming that obstacle changed you?

I have learned a lot about managing my own money. It’s not an easy thing sometimes but I have a lot more confidence in my abilities and having that confidence changes everything.

Life impacting book:  Secrets of the Millionaire Mind

Andrew

Family Money Plan

What is the BIGGEST money obstacle you have overcome?

To spend it? I know, horrible answer, but I do find it hard sometimes to find the balance in enjoying my money and hoarding it away. This sounds like a first world problem (and it is), but I think it is important for everyone to find that balance, no matter where they are at in their money journey. Even if you’re working on paying off a mountain of debt, you can’t deprive yourself. You have to find ways to have fun with your money and work towards your financial goals at the same time.

How has overcoming that obstacle changed you?

It’s been a journey, that’s for sure. However, I think I’ve learned what is worth spending my money on and what is not. That’s been a huge part of it. I just took a trip to Peru which cost a few thousand dollars, and I had no qualms about any of that money going out of my bank account. The $40 I spent on a dress I wasn’t absolutely crazy about though? That one caused me some pain (and yes, I took it back). If you spend your money where your values lie, it’s a lot easier to see it go. And make it seem worth it.

Check out the interview here.

Life impacting book: “Rich Dad, Poor Dad” by Roberty Kiyosaki

Britt

Britt and the Benjamins

What is the BIGGEST money obstacle you have overcome?

Have you ever heard that saying “bad advice is cheap?” It was that for me. When I started learning more about money and sharing what I was learning, people around me were quick to tell me their opinions (why I should buy a house right away, why financing a brand new car is a good reward for finishing school, why I didn’t have to worry about retirement because my job has a good pension, etc.) I think people are more inclined to tell you their “expertise” when you’re a younger person – they’ve lived it and they know what it’s like. I also worked with a financial advisor and because he’s a professional, in the beginning, I listened to EVERYTHING he said and did what he told me to do. So the biggest obstacle for me (and still is!) is filtering through the clutter and hype about money. It’s true when they say personal finance is personal. There isn’t one strategy out there that will fit everyone. Now, I hear out what people say and evaluate whether it fits in with my goals and values or if it’s just another “good-to-know” thing.

How has overcoming that obstacle changed you?

I feel confident in my knowledge of personal finance matters, in my own financial plan, in my goals and in my ‘financial personality’. My knowledge increases the more I learn about the different money strategies and new knowledge there are floating around. I can decided which strategies fit in with my own financial plan and which strategies don’t. And I stand solid behind my ‘plan to become rich’ without falling for every new hype or trend there is.

Check out the interview here.

Life impacting book: Smart Women Finish Rich by David Bach

Jaymee

Smart Woman

What is the BIGGEST money obstacle you have overcome?

The biggest obstacle for me has been creating and sticking to a plan. There are times that I struggle with the balance between learning and implementation. I will try and learn a lot on a subject but then will be very slow to implement it.

How has overcoming that obstacle changed you?

While I still struggle with this obstacle, I have begun taking a lot more action. The biggest motivator to get over it has been creating dashboards showing the current status of my goals that I review on a monthly basis. By utilizing goals and reviewing them frequently, I am forced to face my progress each month so I can keep myself accountable if I end up not taking the necessary actions.

See the full interview here

Life impacting book:  Millionaire Next Door

Thias

It Pays Dividends

What is the BIGGEST money obstacle you have overcome?

I think I struggle with the idea of making more, which sounds so weird. I’m pretty comfortable with frugality and cutting back and taking time to clip coupons or do whatever to scrimp and save, but it’s only recently that I’ve really started to embrace the earning more side of things.

There’s a big part of me that always feels like a crazy imposter whenever I start working on a side hustle – especially with freelance writing. There’s a small part of me that never stops asking why would anyone really care what I have to say?

My mind has all sorts of road blocks up that keep reinforcing the idea that I chose to work in the arts, so I’ll always be kind of broke… and that’s stupid, but it is a constant struggle to remind my mind to shut up! ;o)

How has overcoming that obstacle changed you?

I was always told I could be anything I wanted to be when I grew up, and I guess I really kind of believed it. I know with my day job, I don’t really accept the idea that there’s anything I can’t do in that realm. But overcoming that side hustling/income road block in my mind has changed me for the better. It’s made me realize there’s more to what I can do than I’ve even come close to realizing yet and that my biggest road block is probably always going to be me – which is stupid and I should just get over myself!

Check out the full interview here.

Life impacting book: Money Girl’s Smart Moves to Grow Rich by Laura D. Adams

Mel

Broke Girl RIch

What is the BIGGEST money obstacle you have overcome?

Me. The personal finance community does a really terrific job of calling out consumerism, society, neighbors, and even friends. But that would let me off the hook too easily. I try to be really frank about this on my blog — I’ve never experienced bankruptcy or anything of that magnitude. 

Heck, I even made it through undergraduate and graduate school without any loans thanks to several scholarships, campus jobs, and some help from my parents. My money obstacle, though, had to do with what I was buying. The breaking point literally came when a shelf in one of my closets collapsed. I was sitting in a pile of stuff that I didn’t even like, and I was so incredibly frustrated with myself. 

Instead of saving aggressively, I would save some money from each paycheck. I did pay myself first. But then any extra money I had leftover from side hustling or anything like that went directly into my closet. I was doing everything right and everything wrong at the same time. 

How has overcoming that obstacle changed you?

I don’t shop for fun anymore. If something is worn out, I’ll replace it – but that’s really the extent of it. In fact, I even struggle with replacing things now. Financially, the biggest change is the rate at which our savings grows now. When I see how much I actually can save, it makes it so bittersweet to think about where I could be if I had started this journey sooner.

Check out the full interview here. 

Life impacting book: The Theory of the Leisure Class

Penny

She Picks Up Pennies

What is the BIGGEST money obstacle you have overcome?

Right now, I’m a saver yet also a spender. I know I could be saving a lot more but then I feel that there also has to be a balance. I can’t save every single penny but sometimes I start feeling guilty for spending money too even though I know I’m good at saving money.

How has overcoming that obstacle changed you?

I’m continuously trying to find balance when it comes to saving and spending. It has made me obsessive about reviewing my long-term goals.

Check out the full interview here.

Life impacting book: Smart women finish rich by David Bach

Bola

Clever Girl Finance

“Challenges exist to make you a better, stronger, more resilient person. Never back away from your challenges. Rise to the occasion.”

What is the BIGGEST money obstacle you have overcome?

I’d say the biggest money obstacle is being different from everyone else. It’s acceptable to be in debt, have huge car payments, and blow all your money on clothes, tech, and going out to eat a lot. It’s been a challenge as we’ve curbed a lot of our spending to achieve bigger financial goals. While people on the outside might think we’re misers who have no fun, I think the opposite. By being frugal and only spending money on what is important to us, it makes our experiences that much better.

How has overcoming that obstacle changed you?

It’s changed us for the better. We stopped worrying about what everyone else is doing and started focusing on ourselves. Dave Ramsey (who I know gets a lot of crap from the PF community) always says, “If you live like no one else, so later on you can live like no one else.” That to me means a paid off house, early retirement, and my daughter graduating college without a mountain of debt.

Check out the full interview here.

Life impacting book: Dave Ramsey’s The Total Money Makeover

Vic

Dad is Cheap




What is the BIGGEST money obstacle you have overcome?

The constant challenge that my wife and I face is the balance between spending a bit extra today to enjoy life (i.e. a nice vacation or extra activities / programs for the kid, etc.) vs. deferring consumption for greater spending in future years.

Many people obviously face this challenge, and we haven’t necessarily gone about it much differently than others. However, I would say that we maintained a very skimpy and frugal life until just the last few years at which point we’ve only loosened the belt just a bit. And I think that is the key, as you age and get closer and closer to reaching FI, it seems more appropriate to begin migrating your spending closer to what is most ideal for you and as you envision your retirement.

I will say though, for us, living a relatively frugal life will always be in our DNA. But it is nice to begin enjoying a few more “creature comforts”.

How has overcoming that obstacle changed you?

I wouldn’t necessarily say we have overcome this obstacle since it is more of a constant struggle and there will always be some give and take. But it has definitely changed us. It is just a matter of how you can find enjoyment in life at a low cost. We are constantly combing through our expenses categories to see where we can cut back without necessarily lowering our lifestyle quality.

Check out the full interview here

Life impacting book:  Rich Dad, Poor Dad

JW

The Green Swan

What is the BIGGEST money obstacle you have overcome?

I am much more aware of where my money goes now. Saving now at the age of 30 for retirement is big priority, something I never use to think about before. Although I still enjoy spending money, I see a lot of value in saving money as well. I also don’t look at debt the same way. If I ever get into debt, I would definitely have a game plan and a time frame for myself on how long it would take us to pay it back. Those were things I never thought about before.

Are there any obstacles you are still working on?

Yes, spending money on groceries and eating out. Although we don’t get into debt doing it, I do find myself using funds from other line items on my budget to cover the additional money spent. Also, learning more about investing is really important to me. Luckily, I have my husband which not only finds investing interesting, but works in banking. He manages all the investments in our family, but I would like to really understand it more and get a better handle on it.

Check out the full interview here

Life impacting book: The Total Money Makeover

Pamela

My Money Counts

What would you say the biggest money obstacle has been for you to overcome?

The biggest obstacle for me has been earning more money – because I don’t have much spare time. I have my daughter, I work in the evening already and I also study at University part time too. Now that my daughter has started school, it’s much easier – I have managed to find an extra job in an office for a few days a week where I am still able to get back to take her to school and pick her up.

How has overcoming that obstacle changed you?

As soon as I started earning extra money, my whole outlook changed. I had felt trapped for so long, but I realised that I could earn more and more even working from home. I feel more positive and really optimistic for the future.

Check out the full interview here

Francesca

From Pennies To Pounds

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