Big Sis Briefing: How to Choose Between Two Good Options

Start Where You Are

You’re looking at two different paths. They both have potential. They both come with trade-offs. You feel stuck, not because either one is wrong, but because neither one is clearly right.

This is one of those moments where logic and emotion start to tangle. You feel pressure to get it right. You worry about regret. You fear what other people might think. It makes sense. Big decisions feel personal and permanent.

Here’s the truth.

You can only ever decide with the information you have today. Not with the benefit of hindsight. Not with future knowledge you don’t yet have. Just today’s version of you, making the best call you can. That is all we ever have and that is more than enough.

You’re Allowed to Change Your Mind

You are not signing your life away. You are not stuck. You’re allowed to learn new things, grow and make different decisions later.

What you choose now is not a fixed identity. It’s a next step. A starting point. A chance to explore. If you get further down the track and something shifts, you can choose again.

That’s not failure. That’s being in motion.

Ask Better Questions

When the options are close, try asking yourself:

  • Why does this path appeal to me?

  • Who else’s voice might be influencing me right now?

  • Am I trying to avoid discomfort, or move toward something meaningful?

  • What would I choose if I knew I could handle any emotion that came with it?

Most of the time, you’re not confused. You’re afraid. Afraid of regret. Afraid of shame. Afraid of judgement. Afraid of feeling a tough emotion. That’s not a sign you’re making the wrong call. It’s a sign you’re human. Your brain is trying to protect you. But it doesn’t mean you should stop moving.

The Story of the Sirens

There’s an old Greek myth about a man named Odysseus. On his way home, he had to sail through a narrow channel guarded by sirens. These mythical creatures sang songs so beautiful and hypnotic that sailors would lose control, leap into the sea, and never make it out alive.

Odysseus wanted to hear the song but survive the journey. So he ordered his crew to plug their ears with wax. He told them to tie him to the mast of the ship. He warned them that once he heard the sirens, he would scream and beg to be released. He told them not to listen. No matter what he said.

And he was right. When the moment came, the song was intoxicating. He shouted, pleaded, and threatened. But his crew held the line. They stayed the course. And he made it through.

What That Has to Do With Your Career

Career choices can feel like sailing through that channel. You pick a direction…. and then the siren songs start.

One whispers about prestige. One sings about job titles. Another makes you worry what your family or old boss will think. You start second-guessing. You feel tempted to reverse the decision, even if it was made with care.

That’s not a sign your decision was wrong. It’s just your mind reacting to uncertainty. The sirens are loud, but they’re not telling the truth.

If you can expect those feelings, and prepare for them, they won’t knock you off course. You can tie yourself to the mast. You can hold steady while the storm passes.

Make the Call, Then Back Yourself

There is no perfect decision.

No option that removes all doubt.

That’s not how this life thing works.

What matters more is:

  • Does this path align with your values?

  • Is it the kind of life you want to live?

  • Are you willing to commit to it, even when it feels hard?

You already know how to feel big feelings. You’ve felt doubt, regret, fear and guilt before. You made it through. You will again.

So pick the path that feels most true to you. Then ride the waves. You are capable of staying the course, even when it feels wobbly.

Remember, you’re not deciding on forever. You’re deciding for now and now is all you ever need.

💖

Next
Next

Big Sis Briefing: The Junior Lawyer Hunger Games (And Why Missing a Clerkship Isn’t the End)