“I am out here for you. You don’t know what it’s like to be ME out here for YOU. It is an up-at-dawn, pride-swallowing siege that I will never fully tell you about, ok?” — Jerry Maguire
I help high performing people find careers they love for a living. It’s less of a career and more of a lifestyle. I have no set hours, and I’ll take a phone call whenever my clients need me. I serve them. Not the other way around.
And in order to help my people, I have to know them inside and out. Similar to how a sports agent knows their athlete. Their professional life. Their personal life. Their strengths. Their weaknesses. Their motivations. What town they live in. If they have kids. Etc. I have to know so much about them that if they were to get five job offers, I would have a strong enough opinion as to the one offer they should take. Lives are changed by the recommendations I make, good or bad. And good odds go up the more in tune I am with my client. Poor decisions are made every day. And poor decisions become fewer the more the team is able to put in the work.
But at the end of the day, I can’t help someone, who hasn’t first put in the work to help themself. I can’t pull them along. They are the owner of their story. They are Pinocchio. Me… their Jiminy Cricket.
In order to know what the next company is best for a person, it’s important to first put pen to paper on what the person is looking for in their next opportunity. Only then is it possible to match up what the person wants/needs and whether or not a company/team can fulfill those needs.
One important question I need you to answer
The next time you are considering leaving your job for greener pasteurs, I want you to ask yourself this question: “What do I want out of my next opportunity?”
And I want you to have an answer. I want that answer to be so GLARINGLY obviously not in line with what your current company can provide that it would be embarassing to yourself, to your friends, and to your family if you stayed where you were in place.
Said another way… I want you to know, for yourself, that it’s time to move on. And if it isn’t… I encourage you to think twice. It’s not always greener on the other side. Sometimes, in fact, it’s brown…
And so, here’s the exercise: I’m challenging you to come up with seven things you are looking for in your next opportunity. Not three. Seven. This may take 10 minutes. It may take 10 hours. Or it may take 10 days. However long it takes, it’s important.
As a launch point, I’ve included what I was looking for after my first company. Ultimately, my list was fulfilled by a company called Wayfair in Boston. I want you to make your own. Push yourself to be uniquely you.
When I left my first company, I wanted to:
- See a strong CEO in action: I wanted to see a strong CEO in action.
- See an experienced executive team in action: I wanted to see how a strong leadership/exec team functioned. Being able to see the impact of big decisions made at the top, and how those decisions impact the business and the people.
- Be in a company experiencing hyper growth: I wanted to go to a high-growth company. A company scaling 50, 60, 100+% YOY. I wanted to go to a place with IPO potential, because I wanted to see that transition from private to public and the potential impact internally. Oh, and I wanted to make some money.
- Be in a company that aligned with my values: I wanted to go to a place that cared about things I cared about: accountability, moving fast, ruthless transparency, embracing the CEO mindset (feeling like it’s your business), etc.
- Expand my network of PMs, Marketers, Engineers, Analytics folks, and Designers: I wanted to work alongside really smart, winners. I wanted to work alongside other smart, hard working people. I also knew that someday, I would likely come back for those winners to build my next company alongside.
- Be in a product role with massive scope: I wanted to build up my Product Management skillset and learn to leverage data to make decisions rather than jumping straight to feature development.
- Go to a company with a strong, well known, respected brand: Coming from a company I had been the 1st employee of that was acquihired and small, I wanted a respected company “stamp” people knew. I didn’t want to get pegged as a small-scale startup guy, feeling it limited my optionality later in life.
Company Matching
By doing the exercise above, you’re then able to have criteria you can use to narrow down companeis you’re interested in. In my case, I was able to narrow down the potential list of companies down to about 10 companies by going through each one and seeing if they had what I was looking for from my list. Then, I hustled to network internally at each, found the potential role fits, interviewed, asked for the job, got offers, and ultimately decided on Wayfair.
Spend the time thinking through your own list. What’s important to you for the next stage in your career? Whatever it is, write it down. Look in the mirror and repeat that list 100 times. Say it so many times you can recite it in the same exact order every single time. Re-affirm your list. Then go make that list a reality. You’ll be glad you did.
Appendix
In case you’re struggling to think about what your list is… here are some other things you may be looking for now:
- Mission Driven: Being at a company that has a mission you believe in to the core.
- Leadership experience: Building your own team from scratch.
- Autonomy: Having a seat at the executive table.
- Culture fit: Being a 10/10 (and then obviously define what “culture fit” means to you).
- Flexible work schedule: Being able to work from home 1–2 days a week.
- Complexity: Being in a highly regulated, complex industry and unlocking growth.
- Location: An office within 30 minute commute from your house instead of 1.5 hours.
- Making cash money: Getting paid a lot of money.
- Professional development: Going to a place that puts strong emphasis on professional development.
I hope this was helpful. Now, spend some time thinking/writing what your Top 7 are. Go get it.
