President Barack Obama's tea, briefing and BlackBerry on his Oval Office desk at the White House in Washington, DC. Dec. 12, 2012.
Callie Shell for TIME
By Merrill Fabry
January 12, 2017

Everyone learns on the job, but when you work at the White House the lessons are plentiful and often unexpected. Here is a selection of lessons White House staffers who worked for Barack Obama say they learned as they navigated their jobs over the last eight years.

  1. Be humble. You’re not as smart as you think you are.

    Dan Pfeiffer, former Senior Adviser to the President: I think the most important piece of advice that I would give anyone who’s entering the White House after serving on a winning presidential campaign is campaigns are AA baseball, and the White House is the major leagues. You’re not as smart as you think you are. Pitches come faster. Be as humble as you possibly can, because you’re going to learn pretty quickly that the stakes are different, and the complexity of the decision ­making is different. Even though you know that going in you’ve seen The West Wing, until you get there and realize the consequences of the things happening around you, it’s pretty hard to fathom.

    Jason Furman, Chairman of the Council of Economic Advisers: If you’re in the Trump Administration and you call a Democratic-­leaning think tank to get advice about some problem, they’re going to take your call. They may go out and criticize what you do, but maybe what you’ll do will be a little bit better. The American Enterprise Institute has an annual retreat, and 97% of the people there are Republicans. I go every year. If there’s some equivalent retreat of Democrats, I would certainly advise my successors to go to it. You learn not everything we think is right.

  2. Help comes from everywhere.

    Pfeiffer: There are a lot of really good people at the White House who will help you figure out things like how to live your day-to-day. People work in the mess, and the career employees in the White House are incredibly helpful to people.

    Cody Keenan, Director of Speechwriting: Fortunately the teleprompter guys are military so they know what they’re doing, but yes, always be nice to the prompters. You’re going to rely on people a lot more than you think. I could not do it without our fact checkers and my researchers. Be nice to everybody. They’ll save your butts from time to time.

    Tommy Vietor, former National Security Spokesman: Get to know the Situation Room staff. Bring them snacks. They’re going to be an information lifeline when things get crazy, and they’re nice, brilliant people from across the military and intelligence community. Also they give awesome Sit Room tours if you’re nice.

    Furman: I spent time getting to know a number of key Republican staffers. They weren’t hugely important to what we were doing in 2009 and 2010. As it turned out, Republicans chose not to cooperate. But then those relationships really paid off in helping us get things done in 2010 on taxes, in 2012 on taxes, and some of the fiscal issues we were negotiating. Somebody may not matter today, but things change quickly in Washington.

  3. You’re never as high or low as you feel.

    Ben Rhodes, Deputy National Security Adviser for Strategic Communications and Speechwriting: You’re never as high as you feel or as low as you feel at any given time. Even when you’re at the lowest point, when everybody’s criticizing you, this is still the President of the United States and the White House. Even when you are on top of the world and everybody’s talking about how great you are, the world is still a complicated place that’s going to throw curveballs at you. You have to have that sense that every period that you go through will pass.

  4. You’re racing against the clock—be decisive and willing to take the chance.

    Rhodes: You think you have all the time in the world. Especially when you’re at the beginning of the Administration, you’re coming in and you’re on top of the world. But you are racing against the clock from the very first day.

    Rhodes: One of the interesting people I talked to over the years in this job is Caroline Kennedy. She has reflected a lot on her father’s presidency and the sense that he had really hit a stride where he felt like he knew what direction he wanted to go and knew what advice to put aside. I feel similarly with President Obama. He came to fully occupy the office and get more assertive in some spaces, taking a risk or trusting his own judgment. Being willing to take a chance and to enter into an unknown and to be willing to be criticized. That is what ultimately leads to the most rewarding outcomes.

  5. It feels overwhelming sometimes, but it is so special to work for the President. Savor it.

    Vietor: There will be times you feel completely overwhelmed, miserable and under siege. The hours can be brutal, and the stakes are high. But as frustrated as you might feel in the moment, know that you’re going to miss the job when you’re gone. You get to be a part of something that’s bigger than yourself. The people you work with will be lifelong friends. It’s a once-in-a-­lifetime opportunity. Savor it.

    Valerie Jarrett, Senior Adviser to the President: I think one of the pieces of advice that I received was that the days last forever, but the weeks, months and years fly by. And that is very, very true. Every single day I think, Goodness, that day lasted forever. And I cannot believe I’ve been here almost two weeks shy of eight years.

    Rahm Emanuel, former Chief of Staff: If you ever drive into the gates of the White House and you still don’t have a tingle in your spine of how special this is, it’s time to leave. Even in the darkest moments and the toughest slog-­throughs, it’s special. I mean it’s going to be tough, there’s no doubt and advice on that, but if you don’t still have a tingle that this is special, then it’s time to go.

Dan Pfeiffer, former Senior Adviser to the President: I think the most important piece of advice that I would give anyone who’s entering the White House after serving on a winning presidential campaign is campaigns are AA baseball, and the White House is the major leagues. You’re not as smart as you think you are. Pitches come faster. Be as humble as you possibly can, because you’re going to learn pretty quickly that the stakes are different, and the complexity of the decision ­making is different. Even though you know that going in you’ve seen The West Wing, until you get there and realize the consequences of the things happening around you, it’s pretty hard to fathom.

Jason Furman, Chairman of the Council of Economic Advisers: If you’re in the Trump Administration and you call a Democratic-­leaning think tank to get advice about some problem, they’re going to take your call. They may go out and criticize what you do, but maybe what you’ll do will be a little bit better. The American Enterprise Institute has an annual retreat, and 97% of the people there are Republicans. I go every year. If there’s some equivalent retreat of Democrats, I would certainly advise my successors to go to it. You learn not everything we think is right.

Pfeiffer: There are a lot of really good people at the White House who will help you figure out things like how to live your day-to-day. People work in the mess, and the career employees in the White House are incredibly helpful to people.

Cody Keenan, Director of Speechwriting: Fortunately the teleprompter guys are military so they know what they’re doing, but yes, always be nice to the prompters. You’re going to rely on people a lot more than you think. I could not do it without our fact checkers and my researchers. Be nice to everybody. They’ll save your butts from time to time.

Tommy Vietor, former National Security Spokesman: Get to know the Situation Room staff. Bring them snacks. They’re going to be an information lifeline when things get crazy, and they’re nice, brilliant people from across the military and intelligence community. Also they give awesome Sit Room tours if you’re nice.

Furman: I spent time getting to know a number of key Republican staffers. They weren’t hugely important to what we were doing in 2009 and 2010. As it turned out, Republicans chose not to cooperate. But then those relationships really paid off in helping us get things done in 2010 on taxes, in 2012 on taxes, and some of the fiscal issues we were negotiating. Somebody may not matter today, but things change quickly in Washington.

Ben Rhodes, Deputy National Security Adviser for Strategic Communications and Speechwriting: You’re never as high as you feel or as low as you feel at any given time. Even when you’re at the lowest point, when everybody’s criticizing you, this is still the President of the United States and the White House. Even when you are on top of the world and everybody’s talking about how great you are, the world is still a complicated place that’s going to throw curveballs at you. You have to have that sense that every period that you go through will pass.

Rhodes: You think you have all the time in the world. Especially when you’re at the beginning of the Administration, you’re coming in and you’re on top of the world. But you are racing against the clock from the very first day.

Rhodes: One of the interesting people I talked to over the years in this job is Caroline Kennedy. She has reflected a lot on her father’s presidency and the sense that he had really hit a stride where he felt like he knew what direction he wanted to go and knew what advice to put aside. I feel similarly with President Obama. He came to fully occupy the office and get more assertive in some spaces, taking a risk or trusting his own judgment. Being willing to take a chance and to enter into an unknown and to be willing to be criticized. That is what ultimately leads to the most rewarding outcomes.

Vietor: There will be times you feel completely overwhelmed, miserable and under siege. The hours can be brutal, and the stakes are high. But as frustrated as you might feel in the moment, know that you’re going to miss the job when you’re gone. You get to be a part of something that’s bigger than yourself. The people you work with will be lifelong friends. It’s a once-in-a-­lifetime opportunity. Savor it.

Valerie Jarrett, Senior Adviser to the President: I think one of the pieces of advice that I received was that the days last forever, but the weeks, months and years fly by. And that is very, very true. Every single day I think, Goodness, that day lasted forever. And I cannot believe I’ve been here almost two weeks shy of eight years.

Rahm Emanuel, former Chief of Staff: If you ever drive into the gates of the White House and you still don’t have a tingle in your spine of how special this is, it’s time to leave. Even in the darkest moments and the toughest slog-­throughs, it’s special. I mean it’s going to be tough, there’s no doubt and advice on that, but if you don’t still have a tingle that this is special, then it’s time to go.

To read more advice from Obama’s White House team to Donald Trump’s incoming advisers, see the full story here, or pick up a copy of the latest issue of TIME magazine.

Contact us at editors@time.com.

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