Oct. 27, 2026

205: 10 Years of Rejections, Then The New York Times Crossword

205: 10 Years of Rejections, Then The New York Times Crossword
205: 10 Years of Rejections, Then The New York Times Crossword
Side Hustle Hero
205: 10 Years of Rejections, Then The New York Times Crossword

Key Takeaways

  • Mark MacLachlan spent ten years facing rejections before successfully landing his crossword puzzles in major publications like the LA Times and The New York Times.
  • Balancing a demanding full-time career as a chemistry professor and dean with a side hustle requires dedication, with Mark investing 30 to 40 hours into building a single puzzle.
  • Going public with a hidden side hustle can unlock unexpected paid opportunities and professional recognition, as Mark discovered when his colleagues finally learned about his puzzle-making.
  • Crossword constructors can earn anywhere from $200 to $2,500 US per accepted puzzle depending on the publication and complexity.
  • Choosing a side hustle you genuinely enjoy is crucial for persevering through the inevitable slow periods and high-effort stretches where results take time.

What does it take to turn a hobby into a side hustle that lands in The New York Times? For Mark MacLachlan, it took ten years of rejections.

By day, Mark is a chemist and the Dean of the Faculty of Science at the University of British Columbia. On evenings and weekends, he creates crossword puzzles.

After nearly a decade of submissions, his first puzzle was accepted by the LA Times in 2016, and his second ran in The New York Times, where more than 200 puzzles compete each week for just seven spots. He kept his side hustle a secret from most of his colleagues for almost 20 years, and when word finally got out, paid contracts followed.

Even if you have zero interest in crosswords, Mark's story will inspire anyone stuck in that stretch where the effort is high and the results are slow.

In this episode, you'll learn:

  • How a crossword puzzle is built, from theme to final clue
  • What separates a puzzle that gets accepted from one that gets rejected
  • What crossword constructors get paid, from about $200 to $2,500 US per puzzle
  • How Mark fits 30 to 40 hours of work per puzzle around a demanding full-time career
  • How going public with his side hustle brought new paid work his way
  • Where AI helps him, and where it falls short
  • Mark's two best tips to start and grow your side hustle

Be sure to catch the wrapup where I take a close look at the myth of the overnight success, and why choosing a side hustle you truly enjoy matters when the results take time.

Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it!

Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things.

For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/205

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Frequently Asked Questions

Who is Mark MacLachlan?

Mark MacLachlan is a chemist, the Dean of the Faculty of Science at the University of British Columbia, and a talented crossword puzzle constructor who achieved success in The New York Times after ten years of rejections.

How long does it take to make a crossword puzzle?

Mark MacLachlan invests between 30 to 40 hours of work into designing a single crossword puzzle, working around his demanding full-time academic career.

How much do crossword constructors get paid?

Crossword constructors typically earn between $200 and $2,500 US per puzzle, depending on the publication and where the puzzle is featured.

What is Side Hustle Hero hosted by?

Side Hustle Hero is hosted by Joan Posivy, a bestselling author and coach dedicated to helping people build the courage and drive to create successful income sources beyond their regular jobs.