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100

Something that gets on your way and makes it harder for you to achieve an accomplishment:

Obstacle

100

In one's own way:

On my own terms

100

Something that you have achieved:

Accomplishments

100

A trip or activity that includes exciting and/or new things:

Adventure

200

Something you fight to achive:

Battle

200

To understand (something)

Get one's head around

200

 Stepped for the first time

Set foot on:

200

Battle you work hard to overcome:

Struggle

300

An activity that you find hard and dislike:

Trial

300

To try and get what you want:

Go for it

300

When you are the responsible of something:

Be on me:

300

Not taking into consideration:

Let alone

400

A riskier adventure:

Exploit

400

An action you need skill to achive, your also kinda afraid of doing:

Feat

400

To cause something as a consequence:

Trigger

400

The moment when something changes:

Turning point

500

An obstacle that makes it harder to get a result:

Hurdle

500

An unplesant or tiring activity:

Ordeal

500

To push out in big quantities:

Pump out

500

To get on a plane or ship:

Charter