Essays & Confessions/Shopping Smart

3 Strategies That Helped Me Learn To Spend Money When I Don’t Think I “Deserve” To

By | Tuesday, December 04, 2018

Have you ever felt guilty about purchasing something? We’ve all been there. How about feeling guilty about purchasing something that you absolutely, 100% could afford? Many of us have been there, too. Letting go of this spending guilt is something that I am working on, and I’d like to share a little bit of my story with you, along with some tips on how to make spending your hard-earned money easier. If you, like me, sometimes fall into the trap of feeling like you don’t deserve “nice things,” hopefully this post will give you a few strategies you can implement to feel more secure when you spend your money.

When it comes to whether or not you can afford to buy something, it is often a gray area. How do you know if you can really afford something? Shouldn’t you be saving as much as you possibly can? How do you know when you’ve put enough money into an emergency fund, your retirement savings, etc.? There is no bright-line rule for this, and everyone approaches his or her spending differently. Just because you have paid off your student loans, gotten that raise, negotiated a higher salary, or landed a six-figure job, does that mean you can go crazy spending? No, of course not. But it does mean you can probably afford to buy things you didn’t dream of buying before.

Suddenly you can afford things like a weekly trip to Whole Foods, an apartment without three roommates crammed into one room, monthly manicures, or daily Starbucks lattes. You can indulge in these expenses without risking going into or back into debt. So which ones should you buy? I’m here to tell you that, as long as you are mindful not to fall into the trap of golden handcuffs (if you don’t know what those are, check out my overview of them here), which can sneak up on anyone, you absolutely can spend your hard-earned money.

You can spend your discretionary money on things that make your life more joyful (daily lattes!), easy (monthly housecleaning!) and healthy (Whole Foods trips instead of packages of ramen noodles!). What you do with your money is your choice. And when you don’t owe anyone anything, your money is yours to spend.

My Story of Moving to an Apartment I Didn’t Think I Deserved

After years of saving, paying off student loans, and working to make ends meet, sometimes it is hard to spend, even when you have the money to do so. Everyone’s journey is her own when it comes to how much to spend and how much to save. I think, though, that those who are responsible enough to have paid off their debt or to have gotten a handle on their student loans often have an especially hard time spending, even when they have extra cash.

Moving is a stressful time for most people. Moving in New York City is especially daunting, as it involves tight spaces, rented U-Hauls with no place to park, or giving up and hiring an expensive moving company if you just can’t do it yourself. Every time I move apartments I get extremely stressed out — but not at the moving process itself. I actually love packing up my things and doing a de-cluttering process (like this challenge!), as I both pack (deciding what should come with me and what should be tossed or donated) and unpack (deciding for a second time whether the items I packed are worthy of my new space).

For me, the stressful part of moving is the apartment-hunting period. Not because I am afraid I won’t find anything, but rather because I have convinced myself that I do not deserve the nice apartments that I am looking at. Who am I, I think to myself as I am looking at an apartment with a beautiful kitchen, to deserve living in a place like this? And who am I, to go around spending that much money, per month, simply to rent out an apartment? Surely I could find something half the price, without a dishwasher, without a doorman, without windows, in a sketchy neighborhood…Shouldn’t I keep looking?

I had the luxury of living alone in Manhattan for a few years in my twenties and early thirties. I understand that this a ridiculously privileged experience, but I worked extremely long hours at my law firm and was compensated very well for it. I had paid off my student loans and was debt free, so I could live where I wanted to. By no means did I choose the most expensive or fanciest of apartments, but I wanted something that I knew would be safe and comfortable. When it was time to move, I searched long and hard and found the perfect studio apartment for myself. It was tiny, but had an abnormally large kitchen for the size of the space, with brand-new, state-of-the-art appliances.

My landlord had purchased this apartment in the same building he had his three- or four-bedroom home, because he thought his kids’ nanny would live there. She ended up not moving in, but the family kept the extra space and decided to rent it out. The day I saw those “nanny quarters” for the first time, I happened to be meeting up with my parents for dinner that night and I could not contain my excitement. It was within my budget, and it was gorgeous! What was my hesitation, then, my mom asked, when I told them I wasn’t sure if I should go for it?

I admitted that I felt guilty about renting it. Did I deserve to live in an apartment like that, in a building like that? She told me I was crazy for even asking that, and that I should go for it. I signed the lease and ended up loving living in that little apartment, with its beautiful kitchen, for a few years.

Over these last few weeks, it became time to look for apartments yet again. This time, moving into a new place with my boyfriend, we have a slightly larger budget, but I will still end up paying way less in rent than I had for my prior apartments because we will be splitting the costs in half. At every place we saw, I simply could not get over the fact that it felt like I was looking at apartments meant for other, fancier people — not for me. But we found something that was perfect and within our budget, so we went ahead and signed a lease. Since we haven’t moved in yet, it still doesn’t quite feel real.

Impostor Syndrome Strikes Again

Preparing for this current move was the first time I realized my anxiety over moving and the sort of impostor syndrome it brought up in me each time I looked at something I had subconsciously deemed to be “too nice” for me. “Financial Impostor Syndrome,” like Maggie wrote about here, comes in many shapes and sizes.

While I still feel anxious over the new place, I am focusing on working through that. Here are three tips I have for when you are stressed out over whether you “deserve” buying something nice for yourself, whether it be a big investment like renting a nicer apartment or a smaller thing like buying your vegetables at an organic farmer’s market:

3 Things You Can Do When Feeling Anxious About A Purchase:

1. Get a Handle On Your Finances.

  • Make sure you are debt-free (or have your debt managed in a way that makes you feel comfortable and in control).
  • Know exactly how much you earn and how much you owe each month.
  • Figure out exactly how much the purchase is going to cost you. Is it a one-time purchase? Monthly, recurring purchase? Make sure you’ve included taxes and fees in the total, too.
  • Now that you know both your money and the cost of the purchase, if you have enough leftover, ease your anxiety by reminding yourself that you have worked hard to put yourself in this place of financial freedom and that you have run the numbers and have set aside enough for this particular purpose.

2. Free Your Mind.

  • Once you are comfortable with the hard numbers, forget about the amount you are going to spend on the purchase.
  • If it is going to cost you $2,000 a month to rent your dream apartment, and you’ve calculated above that you can comfortably spend that amount, the next step is to clear your mind from thinking more about whether you should or could spend less.
  • Set aside that money and make the purchase if it is what you want.

3. Justify the Expense (Optional Step).

  • Sometimes people use the term “justify an expense” to mean that they have made-up reasons and excuses why they bought something they really shouldn’t have. But I don’t mean it in this way. Remember, you’ve already (1) crunched the numbers and decided the purchase financially works for you, and (2) freed your mind and cleared your conscience.
  • But, if you are still struggling with spending the amount, list out all of the reasons why this particular purchase is going to enhance your life. I like to justify my purchases by asking myself whether it is going to bring me more joy, more time, better health, or a combination of all three.
    • Take my new apartment, for example. I went through this exercise myself and was able to comfort my mind that I was making the right choice. How did I do this? Well, I figured out that:
      • The apartment has a lounge area, complete with tables, chairs, sofas and bright light. I would definitely be able to take advantage of this as a home office and would not have to work in my small apartment all the time, at a coffee shop that I could only work at until I inevitably had to leave when I had to go to the bathroom, or at a paid communal working space. This will save me both money and time and I think I will be even more productive because of the space.
      • There is a farmer’s market right by the building, in addition to two grocery stores that I love. That, combined with the awesome kitchen (with a full-sized fridge and freezer, which I don’t currently have) will mean I can make healthy meals and spend less money ordering take-out or wasting food because I have no place to store it.
    • As you can see, my new apartment might be costing me more, but it is providing so many life enhancements that I can more than justify the cost. Having these justifications written down and top of my mind not only clears me of second-guessing my decision but also motivates me to use that lounge and use that beautiful kitchen so I fully appreciate and get the most value out of what I am paying for.

I still have work to do, but I’m getting there, and using the three strategies above is helping me on my journey to feeling less like a financial imposter who doesn’t deserve to buy things with her hard-earned money. What challenges have you faced when it comes to upgrading your lifestyle or buying yourself new/nice things? Is there any place in your life where you are sacrificing, unnecessarily, that is negatively affecting your life? Could you upgrade just a little bit to make your life happier, easier or healthier?

The Unbillable Life is a former law firm attorney in New York City who blogs about her experiences at a high-paying, yet extremely high-stress, job, and why she left that career (and salary) to pursue something else, which is still yet to be determined.  Learn more on her blog – – because life is about more than just work.

Image via Unsplash

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