You can do it, mama! It's scary at first but it gets easier with practice.
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I wear DB and push DS in a stroller. We have a backpack/harness thingy that comes in handy, too. When I really need to get shopping done in a hurry, I put DS in the shopping cart seat and wear DD in the Ergo. If I want DS to wear himself out, I wear DD and take DS in the stroller to a park, plaza, or safe place to run around. Then I strap him in his harness. Or I'll walk with him in his harness to the play place. I can't really run fast enough to catch him when I'm wearing DD, so the harness is a must.
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The key is to get him used to understanding basic safety boundaries. The only way to do this is to practice them. He always has to hold my hand when we're in parking lots or on the sidewalk by a road, for instance--even in the harness. Gradually we'll go from hand-holding to him always keeping one hand on the stroller or cart. Baby steps.
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And be glad people offer to help! It's harder when they stand and silently watch you struggle with a heavy door and an armful of packages and children. :irked
