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This article was migrated. The article was marked as recommended. Drafting your own letter of recommendation (LoR) is becoming a more common request across all levels of medicine and academia. This can be a daunting task in an environment where metrics for advancement continually increase and meaningful relationships with mentors, supervisors, and leaders are not promoted or easy to come by. The authors recently held a workshop where the challenges, advantages, and pitfalls of writing you own LoR were discussed. In this Personal View article, we took into consideration audience feedback and provide proactive successful approaches based on experience of writing our own LoRs and writing and reviewing LoRs from the level of undergraduate admission to faculty promotion in academic medicine. We acknowledge the advantages and pitfalls of writing your own LoR and offer practical methods/approaches as tools for success.