Interview Series - Career Experts - Jessica Sweet from Wishingwell Coaching |

In this interview series, we caught up with Jessica Sweet and Wishingwell Coaching who shares her expertise and insights about job search, career change, today’s marketplace.

Tell us a little bit about your company

I help people in midlife transition their careers to something that makes them happier and more fulfilled, but also something that actually works for their real life. 

How did you get started in this path?

I left my job as a social worker and therapist after I had my first daughter, and decided that I wasn’t going back.

After doing some soul searching, I started my business. That was 11 years (and another daughter) ago.

Is this something you decided early on in your career?

I’ve always been in the “helping professions,” so that hasn’t changed, but my path was a bit winding. I was a social worker with people with mental health and substance abuse problems, and I did both inpatient (acute hospital) and outpatient (therapy) work with them.

My dad hated his job when I was growing up. That was a huge theme for me. So when it came time to make a change in my career after my daughter was born, and I thought “what do I REALLY want to do?”

I realized I really wanted to help people who were stuck in jobs they hated. It’s not a pain that people have to endure, but it’s one that can rip you apart, if you let it.

What is the most exciting part of working in this industry?

Really being able to help people with something significant. As I said, being stuck in a career you hate can rip you apart.

It’s as real as illness, or divorce, or any other major life stressor, but the difference is that there are often some very powerful things that we have control to change in this situation.

I love helping people see what they can do and watch them do it.

They move from pain to power in a real way, and there’s not many situations where one gets to see such real change in such a short time.

How do to stay abreast of the industry as an expert?


I read lots of different career blogs. I also chat with other industry experts as well. And I learn a lot from my clients too. They’re out there with feet on the street every day.

What are some of the things that you see job seekers struggle with the most?

Figuring out where they can transfer their skills.

What other jobs can I do where my skills will matter.

Confidence as well.

What are the common mistakes that you see them do?

Just looking for any job they can get. They need out of their job, so instead of slowing down and figuring out the right job, they just look for a job.

They hit LinkedIn and Indeed and they start looking, when in reality, the first thing they need to do is ask, what do I really want?

How should job seekers approach job search today?

You have to approach it from the outside in.

It sounds woo-woo and not practical, I know, but I assure you it is the most practical way to search for a job (and approach your career) in the long run.

When you place yourself in a job you like and can succeed at in the long run, you’ll do best, rather than making the mistake I see people make over and over. . .

Unemployment is at the lowest levels, why do you think that is?

Complicated question, and I’m no economist.

Good economy? Fewer people in the workforce? Shrinking sectors (travel & tourism)? There are many theories and it takes someone better versed in this area than I am to have a great theory about why.

The result though is that it can be harder to find a job.

However, people who network will always have an advantage over those who don’t.

What is the biggest trend(s) you see that job seekers will face in the next 2-3 years?

There’s no question that AI will play a big role in the future. My guess is that will mean that companies will do a better job matching jobs to candidates.

In many cases, that will be good, but for other people, that might feel like more pigeon-holing.

Again, a great reason to network!

What is one advice you would give someone just out of college today?

Figure out some goals.

They don’t have to be your only goals, and they don’t have to be immutable, but give yourself something to work toward instead of falling into the next thing. Also NETWORK!

What is one advice you would give someone who is switching careers?


Talk to people doing what you want to do. Learn what you don’t know. Connect with those who can help you.

What is the biggest trend(s) you see that hiring managers will face in the next 2-3 years?

I think the same.

Jessica, what are you currently working on?

I’m working on putting together a group program to help people find their personal brand. It may not sound that exciting, but personal brand is the thing that gets people hired, and if you do it holistically, it feels authentic, not like a veneer that you’ve plastered on for the purposes of job searching.

Doing it in a group setting gives a chance to practice using it, bouncing it off of people, get ideas, and makes it more affordable!

What are the best resources you recommend to job seekers?

There are tons of great ones out there. I spend a lot of time on LinkedIn, just browsing for articles that catch my eye, and I often end up on one of the big blogs, like Forbes, or Business Insider, but you recently put together a list of great blogs, many of which I often browse as well.

I also have to mention my own blog (which made your list!), especially for people who feel stuck in their careers and who are wondering how to transition. I have a lot of info about what to do and how you can make a change.

What is the best way for our audience to reach you?


Connect with or Follow Jessica Sweet on Social Media:

Jessica Sweet and Wishingwell Coaching have also been featured in our recent compilation of the most resourceful career experts and career blogs –  Top Career Advice Websites.   

Written By
Nissar Ahamed is the Founder & CEO of He is also the host of The Career Insider Podcast and the co-host of The C.A.R.E. Podcast

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