[4] After graduating from Cornell, Canaday began his professional running career as a marathoner for the Hansons-Brooks Distance Project, sponsored by Brooks Sports.

That same year, he moved from the Hansons-Brooks base of Rochester Hills, Michigan to Boulder, Colorado, a major center for endurance athletes, and in October announced a sponsorship deal with SCOTT Sports, which replaced Brooks as his primary sponsor.

[13] Wearing Hoka One One shoes that year, Canaday replicated his victories at Tarawera and Speedgoat and also won the Pikes Peak Ascent in August, en route to winning the prestigious The North Face Endurance Challenge 50 mile race in December.

Canaday made a brief summer return to ultramarathoning for the Comrades Marathon, where he placed 15th, and Speedgoat, which he again won, before competing in the Ultra-Trail du Mont-Blanc–his first race of 100 miles–in late August, which he was forced to drop out of due to a knee injury.

[18][19] He continued his ultra-marathon career in 2016, including his second 100-mile race and first finish at the distance, placing 11th at the Western States Endurance Run, having at one point been second and ahead of record course pace.

[26] In 2021, Canaday suffered from a bi-lateral pulmonary embolism and lost his home and most possessions in a fire that destroyed an entire apartment complex in downtown Boulder, Colorado.