Transitioning from being a long-term independent contractor to a full-time employee is hard.

After 20 years of consulting / contracting / free lancing, / working as a one person agency, I'm investigating returning to full-time work. Prior to the pandemic I averaged 50 hours a week in billable hours, since the pandemic, I'm averaging about 20 hours a week because my many of my clients didn't survive the shut downs.  I'm at a point in my life where I don't know if it's worth it to rebuild what I had before I retire in 10 or 15 years.

The big challenges I’m seeing in my job hunt are:

1) Hiring managers who are concerned that I’ll work with them for three months and then leave to grab a contract so they prefer a candidate who has a more traditional background.

2) HR folks are concerned that after working independently for so long, I won't be able to work for a ”boss”. They don't understand that I’ve had many “bosses” in the past 20 years, I just called them “clients”.

3) Many recruiters I’be worked with really don't understand free lancing as far as a job timeline is concerned. I’ve had over 100 clients, some major brands that were long-term engagements, some small companies that needed a week or two of work.  Some engagements are near full-time where others may be a little as a few hours a month.

I list the last 20 years as one position (as I do on my taxes) and mention my major clients in bullet points. Recruiters often request that I list these engagements as separate positions, which makes things convoluted. I can't list all 100 clients and fit my resume on two pages of paper. If I list only my longer-term engagements, there are gaps in the timeline. (Periods where I was doing short term work for small organizations). 

Either way there are overlaps, I'll be spinning up a project while putting another one to bed. I am often providing support a few hours a week to a number of organizations while working on a long-term project alongside it. I know it's not an uncommon story for independent workers but It's just hard to express in a traditional timeline  At the height of my business I had 15 support and maintenance contracts alongside a 30 hour week project, which gave me 40-60 billable hours a week. This morning I had a recruiter accuse of my lying, telling me that it's impossible to have two clients at the same time.