The achievement is earned in the Bad Blood DLC and must be completed solo (Driving Contracts are unavailable in co-op/online).
The objective of this achievement is rather simple, yet tedious. You will need to complete
29 driving contracts (Orange steering wheel icon on the city map), you can either repeat your favorite contracts 29 times or complete each of the unique challenges.
Repeating Challenges: *** Spoiler - click to reveal ***Assuming you have default controls, open up your cell phone by clicking 
on the d-pad and use your 
to navigate to the "Driving Contract" app. Press 
to open the app and you will see a list of the different contract types on the left: (1) Carrier, (2) Escort, (3) Overdrive, and (4) Scramble.
Here you can click on the contract you want to navigate to and it will set a waypoint on your map. Now you can use the closest fast travel point (double yellow arrows icons on the city map) to head to your destination and complete the contract.
TIP: I found the Overdrive contract for Floored Pawnee to be a quick and easy run when I got tired of going to unique contracts.
Driving contracts Options: -
Carrier: Safely bring the vehicle to its destination within the time frame. The goal for these missions is to limit the amount of damage on the vehicle.
-
Escort: Follow a friendly vehicle to its destination taking out enemy vehicles along the way by either ramming them with your vehicle or by using environmental hazards.
-
Overdrive: Race through the checkpoints while maintaining your speed.
-
Scramble: Chase the enemy vehicle and stay close to download their data. (Note:
environmental hazards/hacks are disabled during these)
Recommended Skills Driving skills Skills such as Off-Road Driver (Improves off-road handling), Offensive Driver (causes more collision damage to enemy vehicles), and Precision Driver (lower blowout chance) can help you out here depending on the type of contract you decide to go for.
Hacking Skills If your completing Carrier or Escort contracts be sure to pick up the hacking skills such as Steam Pipes and Blockers to increase your environmental hazard hack options.
This achievement may "glitch." If you get to 29/29 progression for the Driving Contracts (can be seen on your phone progression) and if your achievement is reading 95% still, complete one more contract and the achievement will pop.