I can't remember exactly when I started using this site, but it was back in the glory years when the floor brokers owned "serviced apartments" (filled with meat slicers and Long-Island hookers), vending machine challenges were thrust on unsuspecting interns, and the world seemed to be awash in money, opportunity, and boozy brunches.
Twenty years later and having worked at (or for) multiple BBs, small shops, PE funds, and now run my own (small) fund, I thought it might be helpful to share with you guys a few things I would tell myself now.
Life's not a straight line. The intense competition, rapid changing structural backdrop, and societal pressures you face are somewhat unfairly put on you. Just remember - you are going to be fine. The fact that you are even posting on a site like WSO shows an adaptive attitude that will allow you to figure it out in the end.
Things I would tell my 21 year old self:
- It’s not supposed to be easy. You’ll run into a few people who “fall upwards” and defy all logic – getting that promotion, raising a $1b fund out of thin air, or running their own desk/shop. Learn to ignore the voice in your head that is saying it’s not fair and be happy for them. Insane luck has a small chance of befalling you one day too.
- The job search never ends. You need to always be searching. You need to be having coffees / calls to see what’s out there as things can change rather fast.
- The learning never ends. University is a place to learn how to learn. Just keep grinding and you will know more than most if you stick with it.
- Your colleagues and your boss may not have your best interests in mind. You need to be careful what you share (and how you behave) with colleagues and bosses. In the trenches it’s a game of “Survivor” every day. Chances are you will be backstabbed, lied to, fired, and/or cut out economically. You will likely lose touch with and never speak (or see) many of your old colleagues ever again.
- Embrace difficult conversations: You can measure your career advancement by your ability to have difficult conversations – run towards them and embrace the awkwardness. The first ones feel awkward, but it gets much easier. You don’t have to wait until you’re in YPO to learn how to “clear” things with your direct reports.
- Relationships trump ideas. You are not going to be able to predict where people end up – you’ll be able to make your own luck 5,10, even 20 years down the line when it’s time to start your own fund, company, or find a new career path.
- Learn to be politely aggressive. You can (and will) be able to get in front of anyone. Never stop pursuing the sale / the deal. There were a lot of people I was too nervous to pursue and got cold feet. I wish I had stuck on them. I’m one of them now and realize it takes 3-4 emails or calls to get in front of me!
- If you’re unhappy, the time to make a change is right now. Don’t be a slave to your job, your boss, your parent’s (or society’s) expectations. You’re going to wake up in 10 years wondering where the time went.
- Learn to be comfortable in your own skin. As a fellow overachiever, the meritocratic society we live in forces us to literally become our resume. You need to let that go. Find something outside of work (volunteer org, hobby, side gig) that can fulfill you.
- The Book that cuts against the grain and will piss off most of your friends: The Management Myth (Matt Stewart)
Cheers,
IBGYBG
Good read, thank you. I’m currently not happy in my group but want to make the move to another internally. In terms of being “more politically” aggressive how would you recommend approaching other members in this team to get my name in front of them for when an opportunity comes up to join their team?
There are (typically) two approaches: “perfection” vs. “brute force”.
perfection: this approach begins by finding a warm intro, getting time on someone’s calendar, and putting the perfect pitch in front of someone.
Brute Force: you plow forward with the “80 percent” solution figuring it out as you go along. It’s a little rough around the edges but you gain ground at the risk of looking dumb. I favor this approach.
Find the guy you want to work with one morning and ask him if he’s got a few minutes and walk down the hall to get a coffee and simply ask him how one would would be able to work for him. One straightforward approach is by asking him what the desks’ challenges are and then you pitch yourself as the solution to them.
beautiful man, thank you
+1
Thank you for taking the time and sharing your thoughts, well written and I can relate to 100% of your points. It hasn't been yet 20 since I joined, but equally a longontime. Since then, it has been a ride with ups and downs, and what you describe is very much on point. Will check your book recommendation.
One of the best posts this year I’ve read! Thanks
Great post!
SB SB
ibgybg really nice post. Salient points. Can you elaborate a bit further on these two?:
"Embrace difficult conversations" - What do you mean you can measure your career advancement by your ability to have difficult conversations? Can you give examples from now vs. then? I don't have problems being direct in my communication style. As I've grown in my career, I know how certain functions are are to be performed and I am comfortable holding individuals accountable in those functions. Is this your point or am I missing it entirely?
"Learn to be politely aggressive" - 1000x this. Do you have any tactical advice here? Any books you recommend? I think this is the most important skill in business as a whole. Written email communications style is passive aggressive, with only as many words that you need. If you're selling, you need to deeply understand incentives and frame value to those incentives, with again, only as many words as you need. Grammar, syntax and semantics barely matter. With in-person business conversations, I think seasoned high-level speak is truly best. In my domain, if you're not speaking at a vague / high-level in introductory / discovery / exploratory conversations, I can learn a lot about where you / your firm stands. You should always be leaving yourself space in business conversations.
Generally, most people are conflict avoidant, preferring harmony and not rocking the boat (myself included - who wants conflict anyway?).
For me, "difficult conversations" means dealing with [uncomfortable] situations head on and avoiding repressing the inner feelings that are signaling to you "something's not right". Perhaps you deserve to be paid more, or are unhappy with your relationship, or you need to lay off an entire division... These are not easy conversations to have but their are tools out there to help you work through them in a neutral, considerate manner.
My outbound is a little different. I know what I'm looking for and I typically express a view. Remember, you can't build a relationship with anyone over email - you need to get on the phone or meet in person.
Great post. One addendum to colleagues potentially not having your best interests in mind…
If you are lucky enough to find a smart and motivated boss/mentor/colleague that supports you and has your interests in mind, do what you can to embrace this. People early in their careers have no idea how rare this situation actually is, and in the short term maybe leaving this kind of situation for a small bump in pay or prestige might seem like a good idea, but this is a long game with rewards compounding exponentially in the 2nd and 3rd decades.
1. Never trust anyone at work
2. Nobody at work is there for you or is there to be there for you
3. Like love triangles, there are politics triangles
I wish sum1 told me this
Great post. How did you always stay on the job search during your career? Any extra advice in that area?
Here is what I sent a recent grad on tips on how to network that you might find useful:
These are really, really good man. I'm saving these and sharing them in the future.
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