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I feel like I have to choose: my boyfriend or my dream

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Dear Grace,

I graduated from high school, but never did any additional education since I ended up taking care of my grandmother who got sick around the time I finished school. Now I’m 28, and I can see other people my age moving up in their careers, while I feel like I’m standing still. I found some courses at the community college that I could start with to get an Associate’s Degree in business management, but when I mentioned it to my boyfriend (we live together), he was just kind of dismissive and blew me off. He said that we couldn’t afford for me to work less so I can go to school, but I think we could swing it if we tightened our budget a little bit. I’m torn—should I stay with and help support him when he won’t support me and my needs?

– Undereducated


Dear Undereducated,

What a letter. I’m so glad you wrote it. It takes a lot of courage to acknowledge and embrace our dreams, particularly the ones that might upend our status quo.

I hope you’ll be comforted to know the good(ish) news that you’re far from alone. There are plenty of Americans that go back to school each year and face the same question: How do I make this work? The even better(ish) news is I have some wisdom to share, both to help you sort through the finances and the dynamic with your boyfriend. 

Invest in what excites you. As you figure out what your next step is to becoming a business management whiz, practice asking yourself “why” at every possible opportunity. Getting clear on your end goal and what is driving it is the foundation of any strong plan. Once you know your “why,” talk to people in related industries or jobs. Figure out what they’d do differently, what they’d do again. You’ll be surprised at what you find and you might even find an easier route to get to where you want to be by talking to people who are already there.

Run the numbers and map out a plan. It’s easier to get on board with a plan that breaks down the “what ifs?” Call your college of interest and speak to a guidance counselor to see how much it will cost you to earn your degree of choice. 

Some of your high school classes may have earned you college credits, so be sure to have your high school transcript in hand when you call. (Hint: call your high school and ask them how you can get a copy. They might even be able to email it to you.) Another way to earn inexpensive college credits is CLEP tests, which allow you to read free guides from the library and then inexpensively test out of some required college courses. 

Now that you know what the sticker price would be for your degree, look at your savings and monthly budget to see what you could cover yourself and where you could use some help. Your partner may be willing to help out when he sees the actual numbers, but even if he isn’t willing or able to step up, you can explore taking out student loans (make sure you do your research before you sign on the dotted line). 

Reflect on your relationship. I’ll be frank—you deserve a partner who gives as much as you do. You asked: “should I stay with and help support him when he won’t support me and my needs?” to which I’ll respond: imagine the purest, sweetest version of your inner child. If she’s anything like mine, she’s probably sporting a homemade tie-dye shirt and a toothy smile.

Now, imagine you asked her this question: “should I stay with and help support him when he won’t support me and my needs?” And listen to what comes up. It’s easy to slip into a pattern of putting everyone else’s needs and comfort before your own, but let me make this clear: you deserve support as you pursue your dreams.

I’m rooting for you,

Grace <3