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You are here: Home / Vocabulary / 100 Words to Use Instead of “Challenging”

100 Words to Use Instead of “Challenging”

February 28, 2026

100 Words to Use Instead of

No. Term Definition
1. Achy Causing physical discomfort or soreness.
2. Adverse Unfavorable; likely to cause harm.
3. Aggravating Annoying; making something worse.
4. Arduous Requiring great effort; strenuous.
5. Austere Severe; lacking comfort or ease.
6. Backbreaking Extremely physically demanding.
7. Baleful Threatening harm; ominous.
8. Burdensome Hard to carry; onerous.
9. Byzantine Overly complex; labyrinthine.
10. Catch-22 No-win situation; self-contradicting rules.
11. Complicated Difficult due to many parts.
12. Convoluted Twistingly complex; hard to follow.
13. Crucial Demanding careful attention; pivotal.
14. Daunting Intimidating; discouraging to attempt.
15. Demanding Requiring much effort or skill.
16. Dire Extremely serious; urgent.
17. Distressing Causing anxiety, sorrow, or pain.
18. Draining Exhausting; sapping energy.
19. Dreadful Causing fear or great dislike.
20. Dutiful Requiring conscientious effort and care.
21. Exacting Requiring precision and high standards.
22. Exasperating Irritating; provoking frustration.
23. Exhausting Very tiring; depleting strength.
24. Expensive Costly; hard on a budget.
25. Fateful Having serious, lasting consequences.
26. Fiddly Tricky; requiring careful small work.
27. Formidable Inspiring respect; hard to overcome.
28. Fraught Filled with tension or problems.
29. Frustrating Preventing success; causing annoyance.
30. Grave Serious; weighty in importance.
31. Grueling Extremely tiring and demanding.
32. Harassing Persistently troubling or pressuring.
33. Hard Not easy; requiring effort.
34. Harsh Severe; unpleasantly rough.
35. Hectic Very busy; full of pressure.
36. Herculean Requiring enormous strength or effort.
37. High-stakes With serious consequences for failure.
38. Imposing Intimidating by size or seriousness.
39. Inconvenient Causing trouble; not suitable.
40. Intricate Detailed and complex; hard to grasp.
41. Irritating Annoying; provoking impatience.
42. Jagged Rough; uneven and hard to navigate.
43. Jarring Unsettling; unpleasantly abrupt.
44. Jeopardous Risky; exposing to danger.
45. Jittery Nervous; uneasy under pressure.
46. Laborious Taking much time and effort.
47. Labyrinthine Like a maze; confusingly complex.
48. Loaded Full of implications; hard to handle.
49. Long-winded Overly lengthy; hard to sit through.
50. Lopsided Imbalanced; awkward to manage.
51. Menacing Threatening; suggesting danger.
52. Messy Disordered; difficult to sort out.
53. Mind-bending Very difficult to understand.
54. Nerve-racking Causing anxiety; stressful.
55. No-win Impossible to succeed in.
56. Noteworthy Requiring attention; significant.
57. On thin ice In a risky, unstable situation.
58. Onerous Burdensome; oppressively difficult.
59. Oppressive Heavy; causing discomfort or stress.
60. Ordeal-like Like an ordeal; severely trying.
61. Painful Causing physical or emotional hurt.
62. Perilous Dangerous; full of risk.
63. Perplexing Confusing; hard to understand.
64. Pesky Annoyingly troublesome; bothersome.
65. Precarious Unstable; likely to go wrong.
66. Pressing Urgent; requiring immediate action.
67. Problematic Causing problems; difficult to resolve.
68. Punishing Harshly difficult; very demanding.
69. Risky Involving danger; uncertain outcome.
70. Rocky Full of obstacles; unstable progress.
71. Rough Difficult; not smooth or easy.
72. Sapping Draining strength or motivation.
73. Severe Very intense; harsh or strict.
74. Shaky Uncertain; unstable and unreliable.
75. Sobering Making one serious; hard to accept.
76. Sophisticated Complex; requiring advanced understanding.
77. Sticky Tricky situation; hard to resolve.
78. Strained Under tension; difficult to sustain.
79. Strenuous Requiring great physical effort.
80. Stressful Causing mental strain or pressure.
81. Stubborn Hard to change; resistant.
82. Tangled Complicated; difficult to untangle.
83. Taxing Demanding; tiring to do.
84. Tedious Long and boring; hard to endure.
85. Tense Nervous; filled with strain.
86. Testing Putting abilities or patience to trial.
87. Thorny Full of difficulties; tricky.
88. Tough Hard to do or deal with.
89. Trying Difficult; requiring patience.
90. Uncomfortable Causing unease; not pleasant.
91. Uneasy Anxious; not at rest.
92. Unforgiving Harsh; allowing little margin for error.
93. Unpleasant Not enjoyable; hard to tolerate.
94. Unwieldy Hard to handle; awkwardly large.
95. Uphill Requiring extra effort to progress.
96. Vexing Annoying; causing frustration.
97. Wearing Tiring over time; exhausting.
98. Weighty Serious; important and demanding.
99. Worrisome Causing concern; troubling.
100. Wrangly Hard to manage; requires effort.
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