Questions We All Should Ask Ourselves About Our Careers

It is easy to get stuck in the daily grind of client work without taking the time to reflect on where our individual careers are going. I’ve been chatting with a bunch of the unconventionally employed I know to better devise a list of questions we should all ask ourselves to make sure our long-term plans are on track. I’ve listed them below. If you have any additions, I’d love to hear them in the comments or via this form.

  1. What is my North Star? Some people like to phrase this with a specific time period (such as: what’s my five-year plan)? 
  2. What steps do I need to put in place to achieve that North Star?
  3. What parts of my job can be outsourced? Doing everything on your own is hard. Maybe there’s something that can be given to someone else so you can focus on growing your business?
  4. What am I doing to ensure self-care? This is good advice for all humans, but the unconventionally employed should take greater care to talk about their hardships and challenges or to otherwise ensure they have time for themselves?
  5. What’s the one thing that requires the most improvement? It’s tough to devote non-billable time to skill enhancement but it’s important to keep up to speed with changes in your industry. Otherwise, you could find new jobs to be hard to find.
  6. How can I strengthen my network? It’s a never-ended struggle to ensure you grow your leads and you keep them warm.
  7. Are my systems set up correctly? How are you capturing leads? How are you keeping track of outreach? Accounting? Taxes? Make sure everything is humming along.
  8. Is this really what I want to do? If it’s not, then the grind is going to hurt more than if you’re having fun. Always self-assess to make sure you’re enjoying what you do. If not, it may be time to try something else/