Many things can squelch our attempts at being assertive — before we ever even start to express ourselves. In a previous piece we talked about three obstacles that stall assertiveness: a sinking self-worth; our fear of disconnecting with the other person; and lack of communication and emotional management skills.

Because there are many other obstacles, we asked two different clinicians to share their thoughts. Below, you’ll find five more obstacles and practical ways to overcome them.

1. You don’t know what you want.

Being assertive is about expressing your thoughts, feelings, needs and wants. But sometimes you don’t even know what those are. Maybe you’re too busy focusing on others. Maybe you’re running on autopilot and rarely look within.

According to Rebecca Wong, LCSW, a relationship therapist and founder of connectfulness, “in order to clearly and calmly express yourself you first need to tune into and understand yourself.” What does this look like? It includes pausing more often, slowing down and sitting with your feelings, she said.

Wong suggested looking particularly at what makes you angry and defensive, because often more vulnerable feelings and unexpressed needs lie underneath. And often these unmet needs have to do with connection. So your needs might include, she said: “I want to feel wanted or desired;” “I want to feel like I matter;” I want to not feel dismissed.”

Psychotherapist Ali Miller, MFT, suggested setting an alarm every 10 minutes to connect with your current feelings and needs (what needs are being met; what needs are unmet). “If you notice an unmet need, see if there’s a request you have of yourself or someone else to help you meet that need.”

2. You think your needs don’t matter.

It’s hard to ask for what you want if you don’t believe that your needs matter,” said Miller, also founder of The next time you’re going to have a conversation about your needs, she suggested saying this statement to yourself: “Everybody’s needs matter; that includes me.”

If you’re really struggling with believing that your needs matter, explore this with a therapist, she said.

3. You forget the other person is human, too.

“If you’re scared of asking for what you want, it might be because you’re not seeing the humanity of the other person,” Miller said. Instead, you might be hyper-focused on their role or position (such as your boss, parent or older sibling), she said.

Remind yourself that this person is a “human being, just like you, who is also trying to be happy and get their needs met.” (See this piece and this piece for being assertive with people you find intimidating.)

However, if you tend to be more aggressive, reminding yourself about the other person’s humanity can help you shift toward being assertive, Miller said. “We all want to be treated with respect and consideration. Remember, everybody’s needs matter.”

4. You’re frazzled or flustered.

When you’re trying to be assertive with someone, and you start getting anxious, it’s hard to think clearly and rationally, Wong said. After all, when we’re triggered, we go into our fight, flight, freeze response (i.e., survival mode). “Often what happens is that instead of being able to tune in and mindfully speak your mind, we get big (aggressive) or small (passive) in response.”

When you’re flustered, it’s easy to blurt out “Yes! Sure!” when you really mean “No, thanks. No way!” Wong recommended taking a deep breath to calm down and soothe yourself. Secondly, if you’re unsure about how to respond, be honest. Tell the person, “I need a minute” or “I’ll get back to you later,” she said. If it’s a request, you might say, “I’ll need to check my availability or schedule.”

5. You’re insecure in your abilities.

That is, you don’t have confidence in yourself that you can be assertive. Wong reminds her clients that part of succeeding is failing. A lot. “The more we try to do something, the more it doesn’t go perfectly, the more experience we gain. And by the time we get it, we know we got it.”

In other words, making mistakes helps us learn and become more effective. For instance, Wong said, when being assertive, you might need to go back to someone and say, “I forgot to say this …” or “I fumbled here,” or “I might’ve offended you when I said this…” This is OK.

Like any skill, being assertive requires practice. Wong stressed the importance of resetting your expectations. Don’t expect yourself to fully understand assertiveness right away. Expect blocks and bumps and detours. And like anything in life, expect it to be a process.

Businessman photo available from Shutterstock