Top 5 Business Regrets

April 28, 2020

Allow me to start out your day with a hot take: you should consider working for free right now.

Yes, you.

The college student about to enter a brutal job market. The seasoned leader that got RIF’d. The individual contributor at a fast-growing company with no cares in the world. Everyone should consider doing some sort of work for free.

Yes, me. And I am.

If you’re early on in your career, this advice is obvious. The hard reality is that you’re about to enter one of the toughest job markets in 100 years. As of this writing, we have about 26 million people unemployed in the US, with the number continuing to rise steadily. You’re young, nobody knows who you are, your skills aren’t developed yet.

Here’s what you can do. Find people that are killing it in your field, reach out to them, and ask if there is some extra work you can take off of their hands and you’ll do it for free. There are folks out there who’ve never been busier in their professional lives. There are a lot of people that would gladly let you help them out. This is a great way to build out your network with people that can teach you and add a lot of value to your career.

If you’re the seasoned leader that got laid off, you need to consider working for free too. The good news is that you have a lot of experience to share with people that are eager to learn. How about giving advice and consulting folks earlier in their career who need help? I’m doing some of this every single day right now. Just offering to help folks for free who need a bit of guidance.

Here’s a plan you could begin with and execute on. Start writing content, joining (or creating) podcasts, and contributing on LinkedIn. Start sharing your experiences and stories on these platform. Comment on people’s posts. Share your opinions. Add people as connections and try to build up relationships. The easiest way to build up your personal brand is to be visibly adding value on LinkedIn.

Even if you HAVE a job right now, you could be working for free. No company and no individual is safe from a pandemic. Anything can happen. Even if you look on the positive side, you can use this as an opportunity to expand your opportunities and fast-track your career. Why not work for yourself for free right now? Maybe now is a good time to work on your side hustle[s] and launch that new business idea you have, or crystalize your business plan.

Don’t tell me you don’t have time for this. Shave off some of those Netflix hours and put in some extra work. My good buddy Morgan Ingram said: “Binge growth, not Netflix.” Even if it’s just for a few hours per week. This isn’t about “job security”, it’s about “employment security.” You want to be as valuable to those around you as possible so that if shit ever hits the fan (it will), you’ll be saved.

I loved this blog from David Rock on how he got his job working for Gary V. He wanted to fast-track his career but wasn’t sure where to start. So what’d he do? He contacted Gary. He was professionally persistent. He worked – you guessed it – for free to show his value. After one video, Gary hired him full-time and now “D Rock” has a massive following.

This got me reflecting on regrets and mistakes I made earlier in my career. I thought I would share them here with you.

Top 5 business regrets:

1) Working for tyrants – allowed myself to do this too often. Didn’t know any better. Felt powerless. Once got an email at 11pm asking me to produce & present something by 8am. Lacking boundaries & living in fear, spend most of the night creating it. Can’t believe I allowed that to happen.

2) Didn’t swing for fence enough – Killing myself for yrs for a significantly lower exit event is not a mistake I’d make again. If you’re going to pour your heart & soul into something, take a big swing & make sure it will be as rewarding as possible.

3) Didn’t vet founders enough – Should have dug deeper into their ambitions, personalities, leadership style etc. One big whiff on my resume haunts me still and this ties back to #1 above as well.

4) Understand equity more – Took cash over equity as first time VP Sales, dumb. Later on, didn’t comprehend the reality of what I might make in an exit & falsely thought it would be bigger. The game is rigged, so you better know how to play it.

5) Develop multiple streams of revenue sooner – Didn’t begin secondary stream of income until 28. If you think you’re going to get rich & save a ton of money, off strictly your f/t job’s income, you’re wrong. Avg millionaire has 7 streams of income. Get cracking on your side hustles.

It’s a good time to share your experiences with others. Here are a few things to watch/read/listen to this week:

Becc Holland and I joined Mike Smalls of Hoopa.

Danielle Mills published her first book: How to Master Linkedin

Collin Cadmus, Richard Harris and I got into Equity


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