I would not encourage you to go into administrative assistant/administrative suppport work, as these jobs are disappearing, and will be even less available as more people do their own documents through voice recognition.
If you're successful at Data Entry, you're probably fast on the keyboard. Would you enjoy computer coding, graphics design, medical coding or records administration? These might be areas to get skills in. If you're on unemployment, you may be eligible for Section 30 training. Be careful though, a lot of these programs just want your money--whether they're for-profit or nonprofit. Check the placement rates, and ask which portion of placements are part-time or temporary jobs. They use these, as the government does, (regardless of political party) to inflate the number of job seekers who are "employed," and deflate the actual "unemployed/underemployed"-underpaid temp and part-timers numbers, to come up with a lower unemployment rate.
I don't know how it works in other states, but Mass has a "bait and switch" training eligibility system in my opinion. Because you are eligible for Section 30 Training, for example, the funding is separate. The former is available when you have an eligible UI claim; the latter (funding) is available "once in a lifetime." So, unless you're wealthy enough to afford thousands of dollars to pay for training yourself, you can never avail yourself of training outside the library, if you are UE > 1x. A longer, classroom experience is a better, more thorough path to real expertise before you get to use it on the job.
Try to get a college degree, and apply for grants and loans if you qualify for funding and don't have the money yourself. If you live in Boston, stay there. There are more training programs available to Boston residents vs. someone who lives just outside Boston, and may be just as low income.
Learn travel arrangments, especially international, calendar management, and event planning--necessary for ExecAdm