Dear Ken… Is he holding me back?
I’ve added a page where you can submit advice letters, and we’ve already received a few! Dat is so crazy. Feel free to send in your questions on the ‘Dear Ken’ page. Let’s see how we can support each other. Sarai wrote in and gave permission to use her name—I'll leave comments on just in case you'd like to add your thoughts two cents.
Letter
Subject: Is he holding me back?
Message: Hi Ken,
I'm nervous writing in because I'm ashamed of what I’ve accepted and confused about what to do please keep me anonymous. I am a 26(F) and have been dating and living with a 29(M) for 2 years. I met him at 22, but we were off and on for a year. We made it official about 2 years ago and moved in 3 months later (I know, I know).I work in corporate tech and am considering going back to school for PM, which is what I’m writing in about. My boyfriend does not have a college degree and recently graduated from the police academy. He went to school for a couple of years but didn’t finish. He has negative views of college and talks about it being a waste because “we get debt for a piece of paper.” I don’t feel that way and want to continue advancing my degree especially with the times we’re living in.
Before he joined the police force, he was working at Amazon and had some part-time jobs. He paid the bills but didn’t have a lot of money, which didn’t bother me since we were young we made it work. I encouraged him and motivated him to join the force.Now I’m trying to go back to school. I’ll take out loans, and my job will help with tuition, but he’s not supportive. In a recent conversation, he said that if I go back, he will break up with me. When I talked to him about it, he said he was joking, but I don’t think so since he’s been saying stuff like this often. He says it will take time away from him and that I should be satisfied with where I am now.
A huge part of me wants to run because I know it’s not okay for him to say that, but I value marriage and want to be a wife. My family is looking at me like I should be a wife to him too. I’m the first in my family to get a degree, so they think I’ve already reached my success.I just need to know what should I do? Or, I know you can’t give me advice, so what would you do? Do I put the career stuff to the side and focus on my relationship, maybe get some certifications? Or do I go back to school because he says he won’t break up with me?
To be honest, I’m okay if you drag me for filth as long as I’m anonymous. I just need someone to tell me the truth and what I need to hear. I don’t want to run this through my friends because I’m so embarrassed.
Sorry this is so long.
Response
Leave Him. The fact that you’re questioning what’s best for you tells me that deep down, you already know the answer. You just need someone to say it out loud.
Leave him.
Point blank, sis. Anyone—whether it’s a boyfriend, a friend, or even family—who wants you to stay stagnant, dim your light, or put their insecurities ahead of your growth is not someone you need in your corner. A boyfriend worth building a life with wouldn’t see your dreams as a threat to his. He wouldn’t joke about breaking up with you or tell you to be satisfied with “enough.” A husband—a real partner—would either support your goals outright or work with you to figure out a plan to make them happen together. This man is doing neither. Leave him.
You mentioned your family think you’ve “already reached your peak” because you’re the first in your family to get a degree. I know that pressure hits deep, especially for first-gen people. But you don’t owe anyone a version of yourself that makes them more comfortable. That’s their opinion— don’t make it your reality. You are you—a woman with ambition, vision, and drive. That doesn’t stop just because others are satisfied. You didn’t work this hard to stop now.
And let’s talk about his comments on college being a “waste.” Look, the times we’re living in are hard, and degrees do matter. It’s not just a piece of paper—it’s access. It’s mobility. It’s options. Don’t let someone’s bitterness or fear of being left behind convince you otherwise. If you’ve got the opportunity to go back to school, especially with your job helping out, take it. That degree will open doors for you that he might not even see because he’s too busy trying to block them.
Leave him.The bigger issue here isn’t just the degree; it’s his mindset. When a man shows you who he is, believe him the first time. The jokes about breaking up aren’t just jokes—they’re manipulation wrapped in humor. The idea that you should be “satisfied” with where you are? That’s a red flag waving high. He’s not worried about the time you’ll spend in class; he’s worried that you’ll grow in ways that he won’t. He’s scared of being left behind, and instead of doing the work to grow with you, he’s trying to hold you back.
This is a dilemma women face way too often. Society teaches us to prioritize relationships and sacrifice for love, while men are told to focus on their careers and get their life together before even thinking about marriage. Sis, we need to take a page from their book. Build your life. Invest in yourself. Put yourself first, because when you do find a partner who’s worthy of you, they’ll be ready to meet you at your level—not drag you down to theirs. Leave him.
Because I’ve lived it I know you can love someone deeply and still choose yourself. I spent my 20s growing in a relationship, and let me tell you—prioritizing my dreams, even with a ring on my finger, changed everything. No partner, no matter how much you love them, should stop you from chasing what’s yours. People can wake up one day and decide to live differently in a way that no longer aligns with you. Trust me. That’s why it’s so important to build your life around you and not what anyone else thinks, says, or does.
I am beyond grateful that I stayed the course, no matter what my partner was doing. He knew better than to try to stop my dreams, because nothing about me gave him permission to think I’d settle for less. And that’s what I want for you—that confidence. That knowing. That “I’m that girl, and you’re not going to talk me out of it” energy.
Check in with yourself. With your spirit. Look in the mirror and remind yourself of who you are and where you’re going. Your journey is yours. Your identity is not tied to marriage or being a wife. It’s not even tied to your career—it’s tied to the woman you’re becoming. And that woman? She’s not about to let anyone hold her back, especially someone who doesn’t see her worth.
Ask yourself: How do you want your future husband to treat you? How do you want him to joke with you? Something tells me this ain’t it. The man for you will never make you feel small. He won’t “joke” about breaking up with you or tell you to be satisfied with less. He’ll be the one cheering you on when you’re tired, reminding you why you started in the first place, and building with you—not against you. And truthfully, you’re putting a husband dilemma on a guy who is just your boyfriend.
This man you’re with now? He’s harmful, sis. His words, his attitude, his energy—it’s all weighing you down. And you don’t deserve that. Move around. Choose yourself, your goals, your dreams, and the life you want to create. The right partner will respect you for it.
You are that girl—and if you need to hear it again, go up to that mirror. Look at yourself and tell yourself your journey is yours. You will reach your goals and won’t be around anyone who wants you to think small. Let him go. Pack his negativity, insecurity, and jokes up in a box, and leave them at the curb where they belong.
You’ve got work to do, dreams to chase, and a life to live—and it’s time to get started.
With love and all the confidence in the world,
Ken
