Once you start career mode with the Cubs and you progress to the Free Agent signing period within the first couple weeks, try to sign as many good free agents as you can. When you can sign free agents, scroll down and click on Transactions, scroll down more and click on Free Agents. Once you see the list of free agents, scroll to the left so their overall rating is highlighted and click twice on the . This will sort the players and have the best players at the top. Make an offer to a lot of good free agents, make it a really high salary for a lot of years so they accept it. By signing a lot of good free agents, you will have a much better team and have a better chance of winning the World Series.
Once the regular season starts, sim week by week and make sure you win a lot of games. You don’t have to have an extremely good record to make the playoffs, you just have to have a better record than everyone else is your division. To check what place you are in your division, scroll down and click on Stats & Standings, then click on MLB Standings. Your team will be highlighted and it will show what the other teams’ records. Where it shows GB, this means games behind. For every win you have more than another team, this counts as 0.5 GB. Every loss you have less than other teams also counts as 0.5 GB. If you win the division by the end of the year, you will make it to the playoffs. Save after every game you win to make sure you move on to the next round.