If you avoid these 9 difficult conversations, your life will only get harder

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It’s human nature to sidestep anything that feels uncomfortable. We’d love it if everything went smoothly and people just understood what we wanted without us having to say it out loud. 

But you and I know that’s just wishful thinking. The reality is, sometimes we have to speak up about what we want in order to get it. 

As a non-confrontational person, I see you as you squirm in your seat thinking about how to approach certain topics. I know what it’s like to just want to sweep it all under the rug and hope it eventually goes away. 

And I hear you when you say, “Do I really have to talk about it? Please don’t make me!”

Unfortunately, I’d have to say, “Yes, you do.” Because if you don’t, your life will only get harder. Brushing things under the rug only makes mountains, as they say. 

Here are nine difficult conversations we’d all do well to be upfront about, no matter how much we cringe at the thought of it: 

1) Money issues

First up is money – probably the most cringe-inducing topic for me. I hate talking about money; I’m one of those folks who’ve been raised to think that money talk is unseemly. 

So, believe it or not, when I got married, it was something I didn’t dare raise. I thought, it’s okay, we’ll just figure it out. 

But as I quickly discovered, I set myself up for a world of inner turmoil. 

If this is something you don’t talk about with your partner, it’s time to wise up. When you’re sharing expenses and saving up for the future, it’s important to have a clear plan. 

Talk openly about your income, your spending habits, and yes, that insane mountain of debt you’ve been trying to skirt around. 

In fact, don’t limit the uncomfortable discussion to money. If you’re in a serious relationship, you also need to discuss…

2) Long-term goals with your partner

Have you ever asked yourself questions along this line: “Where is this relationship going? What does the future hold for us?”

It’s a classic dilemma, for sure. Should I talk to them about it or not? Should I be patient and wait? Will I scare them off if I bring it up?

Look, we’re all on borrowed time here. As much as we love the people we’re with, we do need to know the overall game plan. Heck, even a blurry picture will do.

You don’t want to go on and dedicate years of your life to a relationship, only to find out that your goals don’t even align. Or that they have commitment issues.

You might want to get married and they don’t. Kids might be a non-negotiable for you, but so is not having kids for them. You might want to relocate to the suburbs, but they’d rather live in the city. 

You get the point. Save yourself a world of hurt down the road and get some answers to those questions in your mind. 

3) Your feelings

Actually, whether you’re in a serious relationship or not, you shouldn’t be afraid to express how you feel. 

It’s basic – our need to be heard and understood. Don’t deny yourself that just because you don’t want to come across as needy or emotional. 

I mean, no one wants to be the “needy” one, but let’s get real here – relationships involve emotions, which can sometimes get messy. 

And if your partner can’t handle that, well, maybe they’re not the right one for you. 

In the past, I had several relationships where I would go along and pretend I’m fine because I didn’t want to rock the boat. Or risk losing the guy. 

Eventually, that constant denial of my feelings led me to feel empty. I realized in the end that I’d rather be authentically myself – messy emotions and all – than pretend to be someone I wasn’t. 

I got a happy ending, though – I did find someone who loved me even on my most upset, angry, and confused days! 

4) Setting boundaries

As I mentioned earlier, I would often go along and pretend I was fine in my past relationships. Even with family and friends, I would do this. 

Don’t make that same mistake. That’s if you don’t want to end up feeling drained and weary of having to please everyone. 

Why do we do it then? Because sometimes it’s more comfortable than saying “no.” 

But think about it – is it really more comfortable? Maybe in the moment, yes. In the long term? Those emotions you’ve bottled up definitely won’t feel light.  

So, go ahead and make your boundaries known. Say “no” if you don’t want to do what people ask of you. It’s going to feel awkward the first few times, but trust me, it gets easier the more you do it. 

5) Sex-related concerns

Is there anything more iffy to talk about than sexual preferences and issues? Sex and intimacy are such complex subjects. 

Even if you’re comfortable in your own skin, discussing sexual issues with your partner can feel tremendously awkward. There’s always that fear of hurting their feelings or being misunderstood. 

I’m not just talking about performance and sexual compatibility here. There’s also the matter of STDs and health-related concerns. 

I believe that conversations around sex can be handled well if you know how. It’s just a matter of approaching the topic gently and sensitively. 

There would definitely be some initial discomfort, especially if you’ve never had to have this difficult conversation before. But it paves the way for a better sex life and a stronger relationship. 

6) Confronting someone who has offended you

Ah, the C word – confrontation

Unless you’re a naturally aggressive person, this word probably strikes some fear in your heart. And what’s even weirder is, it does so even when you’re the aggrieved party! 

Maybe a friend made a comment that rubbed you the wrong way. Or you feel like your partner isn’t supportive.  

For non-confrontational people (like me), it’s easy to convince ourselves that we can just let it slide. 

But let’s be honest – oftentimes, we don’t really let it slide. We just bury it and it builds up resentment in us. It’s just another form of allowing others to disrespect our boundaries. 

So take a deep breath and buckle up for that difficult conversation. Remember to keep your tone even and express yourself respectfully. Effective communication is one of the best tools you have to resolve a conflict. 

And that goes for your work concerns, too…

7) Speaking up at work

Why is this so difficult for many of us? Well, there’s nerves, the fear of ridicule, the fear of stepping on someone’s toes, the fear of earning your boss’ ire…

There are so many factors in the workplace that can keep us from expressing our opinions. It’s just easier to keep our head down and hope for the best. 

News flash: sure, it’s easier, but then you’d be depriving yourself of personal and professional growth.

Consider these examples: 

What if you spotted an issue that could potentially derail a project? 

What if you see unfair labor practices?

What if you have a better idea than the ones currently on the table?

See where I’m going here? Your voice matters, not just for your sake, but for everyone else at work. 

8) Asking for a raise

This one is a double whammy – it involves speaking up at work and money. No wonder it’s universally seen as a difficult convo!

I’ve only ever had to do this once, and wow, it caused me a lot of sleepless nights before I could get around to doing it. 

I felt like I was turning in quality work, but not really getting recognized for it. I’d go to work and do my job quietly, but over time, I started feeling more and more resentful over being taken for granted. 

I finally decided to take a chance; I am the driver of my life, after all. 

What helped me was to think of the worst that could happen…which is that my boss would say “no.” I wouldn’t get fired, nor would I be demoted. 

If you feel like you deserve a raise, don’t waste your time lying awake in bed mulling it over like I did. Document your contributions and make your case. 

Remember, fortune favors the bold

9) Health concerns

Finally, let’s talk about our health. A sobering, ultra-difficult conversation. 

No one likes thinking of all the possibilities when they have a weird ache or a strange sensation. Our minds immediately jump to the worst – and then immediately shut it down and think it’s probably nothing. 

It’s classic denial at work. 

Listen, setting health concerns aside won’t make them go away. And what’s worse is that you could be putting yourself in danger unnecessarily.

That tiny flutter in your heart could have been easily fixed with medication. The mole that suddenly appeared could’ve been easily removed with an outpatient surgery. 

When it comes to our health, the longer we wait, the higher the risk. 

So go see the doctor and take control of your health. Don’t make your life harder when there are treatments available.  

Final thoughts

These topics are tough to talk about, for sure. But think of them as an investment in your future – you want to make sure you get what you really want out of life. 

And more importantly, you want to live life with no regrets. You don’t want to look back and think, “Oh, I should have just said what I wanted to say…”

As they say, no pain, no gain. Tackle these difficult conversations and make your life easier! 

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Roselle Umlas

I am a freelance writer with a lifelong interest in helping people become more reflective and self-aware so that they can communicate better and enjoy meaningful relationships.

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