Sightline Session

Take stock before you decide what comes next.

Some decisions are hard because there’s no obvious answer, and others are hard because there are too many things to consider at once. Sightline gives you a way to step back and sort through what deserves your attention.

What this gives you

An honest read on where you stand and a way to see what your decision is asking of you.

You leave a Sightline Session with two things.

First, a clear picture of how you are doing across 12 areas of your life organized into three dimensions: your relationship with yourself, how you want to structure your life, and how you’re building your career.
Second, a way to look at any decision front of you and understand exactly what it's asking of you, whether you're ready to move forward, or need to strengthen something else first

Sightline may be useful if:

You have a decision that feels bigger than the question on the surface
Several parts of your life are changing at once
You keep going back and forth on something and can’t figure out why
Things are going well, but you want to be deliberate about what's next

Not everything belongs in every decision

See the whole picture, then choose what you're ready for.

It's easy to focus on the decision in front of you and overlook what else it's connected to. Sightline shows you those connections, and which ones matter most.

Take the decision to leave a well-established job for an early-stage startup for example. You'd likely be trading higher pay and stability for faster learning, more responsibility, and greater visibility. Here's where some of the real trade-offs show up:

Trust in yourself. Startups rarely come with a playbook. If you haven’t built confidence in your own judgment and capabilities yet, that environment could leave you second-guessing yourself rather than energizing you.

Purpose. It’s worth asking whether this move is taking you toward something you want or only away from something you don’t like.

Boundaries. Startup culture can easily expand to fill whatever you give it. Knowing what you want to protect outside of work makes it easier to decide what you’re willing to give up.

Finances. You need to have figured out what you're willing to risk and how long you could manage if things don’t go according to plan.

Just as important as knowing the trade-offs is knowing which areas of your life don’t need much attention at all. Your plans for partnership, friendships and community, for example, may have little bearing on whether this is the right move right now.

Sightline puts all those pieces on the table at the same time, so you can see the whole picture. You may discover that something you thought was fixed is more flexible, that what you considered minor matters more, or that the question you started with is not really the question you need to answer.

How it works

The Sightline Session has two components. You begin by completing a guided assessment that looks at 12 areas of your life on your own. We then spend 75 minutes together stepping back from the day-to-day to look at what's supporting you, what may need attention, and what you want to take into consideration as you think about what comes next.

Prefer to start on your own?

Explore the Decision Guide