Sense & Sensitivity

Freelancer Friend Unwilling to Look for New Work

DEAR HARRIETTE: I have a freelancer friend who has been struggling a lot in recent years. I feel bad for him -- he is trying as hard as he knows how, but it’s not working. He can’t pay his bills; his friends have chipped in as we can, but it is clear that he has to make a shift in how he earns money. Several of us have sent job postings his way, but so far, he hasn’t seemed interested.

I suggested he get a part-time job with Uber or Lyft or some other taxi service. I see so many people -- including immigrants -- earning money in jobs like that. Why can’t he? I have even seen a few guys in my neighborhood drive for a while and then open up their own small businesses. My friend seems to have a mental block around this, though. How can I help him? -- Needing New Vision

DEAR NEEDING NEW VISION: Your friend may need a bit of tough love. He is not facing reality if he hasn’t figured out that what he is doing is not working. Because those who love him have helped out whenever they could, he has been able to get by. Perhaps it is time for you to stop with the financial aid.

Remind him that you know many people, including immigrants in your neighborhood, who have gotten creative and chosen to take jobs that pay the bills, even if they aren’t first-choice jobs. Point out that we are not our work. He doesn’t have to identify with the job. He may just need to do something like that in order to tide himself over as he searches for other work. Tell him that you love him and that you see how hard it is for him to come to terms with how tough things are for him right now.

You can also suggest that he go to the local unemployment office. While he may not qualify for unemployment insurance, he may learn about job opportunities in his community as well as job trainings that may help him transition into a paying gig.

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