3 Challenges I Didn’t Appreciate When I Changed Careers

career change challenges

Do what you love! Love what you do! Follow your bliss! There are articles upon articles and books upon books available about pursuing your dreams and finding work that makes you happy. And I believe them because I’m not averse to putting in the work necessary to make them true. However I do wish I’d had the foresight to appreciate a few of the obstacles I might encounter along the way.

Here are my three current career change challenges:

1. Measures of success and progress can be subtle, even intangible.

It’s budget season in my old life. I miss diving into spreadsheets, comparing month over month and year over year results, pondering trends for the upcoming year, setting stretch targets for our departments. I appreciate having tangible goals to work towards. I am still in the early stages of developing my business and while one aspect of it – the consulting piece – comes with the potential for tangible goals, targets feel nebulous for my writing, my photography, and now add wilderness guiding to my ever-expanding list of services offered.

Planner and plotter that I am, I need some reassurance that the work I produce progresses me down a path (more on this below). So I sat down with my husband to build a list of qualitative and quantitative metrics that I can use to evaluate my business. In no particular order they are:

  • new relationships established
  • attitude after trip (i.e. my mental state, how I feel I impacted the people on my trip, how the trip itself impacted them, etc.)
  • skills developed or improved
  • request for guiding services
  • client feedback
  • gut check
  • number of new ideas for photos and essays generated
  • Google Analytics for this site
  • Social media targets
  • $ earned (of course)
  • # of prints or pieces sold


2. The trail is not necessarily direct.

I came out of my undergraduate Finance degree and my Masters of Accounting with a pretty defined career path. It’s not quite as defined with a naturalist diploma. Or if I look at it another way, I have finally learned how to think off-trail, outside the box.


This is awesome – let me celebrate that small win for a moment. Great!


My challenge is learning to bushwhack with a map and compass – which I’m happy doing – when I don’t have a destination marked on that map.


3. Balance is relative.

My work bleeds into my life and vice versa. It’s part of the reason I made a career change. It’s hard to complain about a one hundred hour work week when I’m hiking, kayaking, and biking in Gros Morne National Park with thirteen awesome women. My balance challenge lies with how much of each piece of my business (consulting, guiding, writing, and photography) should I focus on during any given day, week, month, or year.


As I alluded to in the beginning, these are ongoing challenges for me. I struggle with them most days. However I have learned to check in with myself frequently, to continue working on the pieces that feel right, to constantly evaluate the pieces that don’t, and to trust that the journey is as fascinating as the destination.


Up for discussion: What challenges do you face as you ponder – or maybe find yourself in the midst of – change?

Published by Kate Monahan

Travel happy. Outdoors professional. Writer. Photographer. Educator.

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