Last chance to talk me off the cliff

Hi new here, I just finished binging the Free Agents podcast. Like I finished a few minutes ago while driving. I will continue to catchup in the Focused content, but I arrived at the destination I was driving to.

I have been building a engineering consulting practice on the side since November of last year when I put up my squarespace website. ( ) The goal was to become a free agent. I landed one client earlier on for about 15-30 hours/month. Last week I closed on a consulting job that will keep me busy mostly full-time for 6 weeks. Today I am at that job for the kickoff meeting. (That’s where I was driving too, very poetic if you ask me) The plan is for me to give notice to my employer next week and be a full free agent by May 6th.

With the current contracts and my savings I have about a 3 month runway. I would like that to be a little longer, but I don’t think I should pass on this new opportunity just for more savings. I am not happy with the day job for a variety of reasons.

So 1) thanks to Jason, David, and Mike for all that they have shared. It has been very encouraging and helpful while I make this transition. 2) for you free agents out there what is you best advice for me right now? I really like the question that gets asked on the podcast: “what do you wish you could go back and tell yourself when you got started?” 3) now is your chance to talk me off the cliff, but you better talk fast.

Thanks for putting this community together I hope to be part of it.


No one should “talk you off the cliff”. If you’re going to be a free agent you need to know you make your own decisions and accept the consequences.

My advice. Don’t burn bridges, ever. If you take work you don’t enjoy – do it to the best of your ability, earn and build up a good reputation for being reliable, and move on. You will never be able to fall back on “the team” or “the firm” or “the job” to take up the slack. Just remember what “being in charge” entails – it can bring handsome rewards. It also means no safety net.

I’ve been an independent contractor for 15 years. It has paid off better than any corporate job I had. But it also means I’ve taken work for people I would rather not have worked for, I’ve taken projects that were boring, because that work led to better, more fulfilling work and built up my resume of accomplishments.

Keep fresh and knowledgeable about your field of work. Strive to know your industry better than the people who hire you. You want your expertise to be valued, otherwise why would they want to contract with you, so make sure that value is real and has depth. If that means investing time and money in training, advanced certification, or whatever your profession rewards, then do it. And don’t ask your clients to pay for it – that’s a sure way to have doors shut.

Most of all – find time each day to sit back, look in the mirror, and enjoy the accomplishments of being on your own.

(Oh, and get good tax and investment advice for your jurisdiction. There are several advantages under current tax law to being self-employed that offset most or all of the costs of providing your own benefits.)


One of my major struggles with my own free agent journey has been battling small thinking. Some might call it “responsibility” with a wife and 5 kids at home, but I know what it really is - self-doubt. Overcoming it is a constant struggle.

So personally, I’ve found it helpful to ask myself, “what would you do if you knew you couldn’t fail?” Some people will probably hate that question, but for me it’s essential - it keeps me thinking bigger and creates the motivation I need to keep going.

That doesn’t mean you have to take a giant leap… the idea situation is one where your side gig becomes so big it can become your main gig. Sounds like you might be close to that point.

Also, to reiterate what @anon41602260 said, don’t ever burn bridges. I’m a big believer that how you leave one thing is how you enter another.

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Thanks to both of you for the excellent insight.

“Jumping off the cliff” is a bit tongue and cheek. The analogy I have been using is a day job is like a pier and being a free agent is like a row boat. The transition from pier to row boat is always a bit dicey. At some point you have to commit and shift your weight to the boat. If you don’t and try to keep one foot in the boat and one foot on the pier, you will end up falling in the water after doing the splits. To Mike’s point, with this new contract, the side gig is now definitely too big to maintain with the day job and it’s time to step into the row boat with both feet.

Totally agree that burning bridges is a bad idea, I kinda did that with my last job transition 3.5 years ago and now regret it.


I’m not a full time free agent, just a part time one, but I’d still like to chip in.

Make a goal that you can achieve relatively soon, and make some bigger ones as well. Celebrate them all - you’ve worked for this, you deserve to enjoy it!

Plus everything everything else said too of course :wink:

I am at similar junction in my life. I have a day job which I don’t enjoy at all but it pays the mortgage and family expense. I have 15 more years before retirement and if I continue doing what I do, I will not be able to have skills that are in demand by the time I retire and will not be able to contribute. I want to be productive as a free agent before and during retirement and make use of my brains before it deteriorates :slight_smile:

So, I am thinking of going back to school to learn a somewhat related skills (I am in IT industry, have technical background, but what I am doing for the past 10 years are management, sales and some PM work). I am thinking of expanding into IT security, maybe go back to school to learn about Security, change my current job by looking for a Security related job (provided there are companies who want to hire an “inexperience” me).

So, let’s see how that goes. And I hope my brains are still able to absorb new things.


Quick update. I gave my boss my 2weeks notice today. He told me he thought I would do well as a consultant.


That sounds like a great compliment!