Allison cheston

Allison Cheston: FAQs for Developing a Career in Your 20’s (#317)

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Our Guest Today: Allison Cheston

Yesterday, Allison Cheston gave us a crash course on how to get a job in your 20s, and she’s back to answer some of the frequently asked questions related to how to develop a career in your 20s, such as: the intersection of passion vs. skill, over vs. under deliver on a project, intrinsic vs. extrinsic motivation and more.

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Livestream with Allison Cheston (Part 2 of 2): FAQs for Developing a Career in Your 20’s – powered by Happy Scribe

Here I am back with Allison Cheston and we’re both wearing different outfits and the previous session, but I just have to say that there are some follow.

Up questions and we did not coordinate.

We did not coordinate the outfit, but we’re just both wearing something.

Outfit, new.

Day, new outfit, new advice. And Allison. In this case. I think before we hit the record button and as someone again. Remembering all the struggles I had and frankly offering advice to others and remember still back then. Now for the basically for 20 years. All these career advice that’s been given. Thrown around. Sometimes without context. We’re just going to debunk and demystify and really maybe clarify some of those things that are often given to young people. Sound good?

Sounds good. Before we start, I just have to say that that recipe, that beautiful dish that you posted on Facebook the other day with the shrimp and the glass noodles, so gorgeous. It was like welcome summer. It was incredible.

Oh, my goodness. Thank you. How is it? The funny, beautiful my mom and I are actually not really good at plating, which is the kind of a skill people would have. And you know what? I feel like I was just telling my mom earlier today, I said, you know why I love working with the Alison from New York? Is that we can be so real and transparent with each other. There’s like no BS. If something’s not working, you can tell me. I can share with you without dancing around.

We’re very straight.

Yeah, I love it. It’s priceless. And for that reason, well, I love to hear your opinion on this many different advices, but this is the one that find where your passion and skills intersect. So it’s kind of a blanket statement.

Great question. Great question. So, first of all, there’s way too much emphasis on this idea of passion because I think people get very nervous. They feel like, oh, my God, I don’t know what my passion is. How am I going to find a job? How am I going to convey passion when I don’t really have a passion? Very few people have a passion. It’s not something that’s ingrained in us. Hopefully you find something that you really care about, that you really enjoy doing and you find it as early as possible. But it puts a lot of pressure on things. Kind of like that. Find your dream job, find your passion. These are just they’re misnomers and they put a lot of pressure on people. So the first thing I would say is don’t worry so much about whether it’s your passion. We can find meaning in most things that we do. The thing to do is to get some experience and discover what you like, but just put 1ft in front of the other and get started. I was just talking to someone yesterday who said he had a nephew who had graduated from Hamilton college three years ago and he still is sitting on the couch at his parents house without a job.

And you know, notwithstanding mental health issues, that means he’s totally paralyzed. There are so many young people who are paralyzed, and having to find your passion and find a job that lets you express that passion is one of the biggest issues, I think, for people. They just get totally paralyzed.

I love the idea of finding meaning in almost anything and everything you’re doing, and it’s very true. And making that, taking that first step followed by the second and third step, it’s so crucial and not overanalyzing, that is key. Love it. And the second thing that people talk about is about over deliver. Over deliver on everything. The interview, your day to day job, over deliver on that report. What are your thoughts on that?

So I believe in over delivering, but not with everything. You can’t over deliver on everything. I think that there’s a tendency to underdeliver. I think people are frequently looking for the easy way out. And I hear a lot of people in their twenties who say, you know, I just want a nine to five job and I want to leave my job behind at the end of the day so I can enjoy my life and enjoy the things that I like to do outside of work. I don’t think that’s so realistic. I think your are really the time for building your career, building your wealth, so that you can live a comfortable life and continue to generate wealth in your life. Over delivering I think is a really good sign from time to time again. You don’t have to overdeliver and everything, but impressing your managers by going that extra step, taking on that extra project, staying late in order to make sure that you complete something to your absolute best ability. I think that’s really important. And you’ll be recognized for that because you’re constantly being tested and compared to your peers. And if you’re the one who takes on more, who is more enthusiastic, who gets more done, who takes things off your boss’s plate, who anticipates your boss’s needs, that’s huge.

You’ll be recognized for it. And I think that is very important.

You brought up a number of really good points. That number one. As someone in her late thirty s, I can look back to my current portfolio, whether it’s my cash flow or my investment portfolio, which is really simplified. It’s total stock market passive index fund accumulated through investing in four hundred and one K. And just always setting aside something at the time seems so insignificant. Now I get to make choices based on who I want to work with, the projects I want to do. And you’re absolutely right, Allison, that it gives me a tremendous amount of freedom that sometimes I don’t even see or appreciate. But thank you for teasing that out. So that’s number one. Yeah, number two. You brought up a really good point about two full questions. I’ll start with one, which is, how do you anticipate the needs of your boss, your manager, in the right way? How do you start that conversation? You know, a lot of young people these days don’t have to do face to face stuff anymore.

Yeah, it’s such a great question. I do think that young people have been disadvantaged by the lack of in person work. One of the best parts of going to work, especially when you’re young, is that you have informal you create informal networks. You’re asked to participate in things. It’s so much easier when you are side by side with people. You can kind of suss out what’s happening. So I think you have to be much more deliberate about figuring out who your boss is, how they like to work. First of all, you should be direct with your boss. You should say, I’m really anxious to help you to take work off your plate. And I want to help you first by understanding how you work best. How do you want to communicate with me so that we’re most effective? Do you want to have weekly calls? Do you want to have daily calls? Do you want me to send you an email at the end of each day, just recapping what I’m working on? Would you like more man? Do you want to be more hands on, more hands off with me? I would really spell it out, and I think people, for the most part, they’ll tell you they’ll appreciate that you made that extra effort.

In terms of building informal networks, you have to just assume that people are going to want to meet with you and be bold. Ask people in your department, can we meet for a coffee chat in person if you don’t have time. Can I have 20 minutes of your time? I presume so we can get to know each other a little bit since I’m not in the office so much. Make sure that you take the initiative and invite people to have drinks after work one day in person. A lot of people are more in person again, and there are a lot of offices that are going back to at least a hybrid approach. They recognize the importance of people being together. So there are lots of opportunities, but you have to take the initiative. Don’t wait for your boss or some other manager whose work you’re interested in to invite you. Make sure you take the ball by the horn, and again, people will recognize you’re like you’re a go getter.

You know, I love the advice, Alison. It’s even true for the work that I’m doing today with two to three virtual assistants and content managers that, for instance, Anna and I always sometimes as a manager, I proactively ask her, what can I do to help you? How can we work better together? Same thing with Anna, who is ten years younger than I am, would approach and say, hey, how about we set up the notion board this way because we’re both remote to each other. And she said, oh, how about we add this additional column to make sure LinkedIn is posted? Can we add checkboxes here? I mean, every little thing, and especially when you collaborate on a process that works for both of you, it’s groundbreaking, that feeling. It’s like finding meaning in everything that we do. It feels so good.

Yeah. To feel that connection with people. I cannot state enough how important it is to at least meet people in person at least once. I have a client whose job, whose company is based in Tel Aviv and they have a big New York office and recently she was in Tel Aviv and she got to go to the office and it was huge. She said she feels so much differently about all the people she’s meeting with. She feels like she’s already built the relationships. There’s like a shorthand when you meet someone in person. So if possible, I understand it’s not always possible, but if possible, take that initiative. And even if you have to travel a bit to meet with someone in person, I think it really is worth it.

Yeah, exactly. The face to face opportunity. When I was working as a freelancer, whatever the arrangement may be, going to the office really made a huge difference to shake hands with these days, avoiding handshake, but just to see each other face to face, a brief coffee, a coffee break or coffee chat over with someone you work with, it just means so much. I have a question since you brought up about burnout these days, a lot of people and young people as well, we’re trying better ways, more efficient ways to work on something. I find that it’s so easy to sometimes over deliver or under deliver so much. We talked about the detriment of like, under deliver, trying to cut corners. But if we’re over delivering all the time, we experience this burnout and sometimes we don’t know it until we’re in it, until it’s too late. So what are some of your measures, or somewhere in their twenty s or in their 30s about seeing that coming and making adjustments and having a better mindset?

Yeah. So, I mean, this sounds like the most basic advice in the world. I almost don’t need to say it, but taking care of yourself in general, making sure that you are getting enough sleep, exercising most days, like at least getting outside and doing and taking a walk most days, and eating a good diet, it makes a huge difference. People who work very long hours often neglect those things and they tend to go hand in hand. So if you’re working on a big project and you know you can anticipate that you’re going to have a few weeks of really intense work and long hours. You can plan around that. But when it’s finished, take a break. Like, take a day off. Go and do something fun. Like, make sure that you have your rewards in place so that, you know, like, this is a finite period of time. And I know I’m really going to do this fun thing at the end. I think that makes a huge difference to people. This morning, I took this amazing yoga class, and it just felt so good. I was sitting outside my building, I was drinking coffee, and there’s this enormous dead rat sitting in the middle of the grass.

Welcome to New York.

I’m feeling so good. It’s a beautiful day. I’m having my coffee, and there’s just a rat. And I was trying so hard. I was just thinking, like, New York in the summer. It’s so gross. It really is. And then I said, okay, so this yoga class, I’m going to have a good day. I’m going to talk, to Say. We’re going to have a good session. Got my clients and all that. But just to illustrate, like, you just sometimes you really have to work hard to keep your frame of mind relaxed and happy and all that.

Yeah, it’s so true. This is basic. It’s not basic, right? Just because it sounds simple doesn’t mean it’s easy. And I agree completely. You know, what you experience from the yoga class can really offset some of the surprises unanticipated that may come on later. Imagine if that’s all you could see, right? Like, you see the dead rat, and then you have to work 18 hours that day. It’s probably not gonna turn out to.

Be like, oh, my God, that’s emblematic of what my day is going to be like. But not get into that mindset that your day is going to be terrible. Just have those things planned out, but really very deliberately plan those things that you’re going to do to reward yourself. I think that makes a big difference.

The one thing that I do to reward myself, like you said, is going out for a walk and not rushing myself. But even if I have, like, a 2030 minutes break, I actually not measuring my footsteps. But I still want that excuse to go out. I also have a trampoline, like a pretty highend German trampoline. Oh, I have to send it to you, alison you will see that Bella Kogan is the name of the brand, and it’s not sponsored, but Belicon has the best. It’s not made out of, like, wire and metals. It’s like these high end elastic bands, and it’s where I have this rainbow color. And then I just take a break. Like, literally, if I have only 1015 minutes in between calls, I just leave my desk, I leave this room, I go downstairs, I bounce. And the moment you bounce on trampoline, you’re just naturally in a good mood.

Incredible. I love that. Faye nobody’s ever said that to me. That is the most incredible thing. You must feel so good after you do that. So relaxing.

So relaxing.

And there’s something about so weightless. You’re going weightless and just feeling your body moving gently up and down. Oh, it’s amazing.

Yeah. Feeling our bodies can never be in your body overrated because being in your body feeling something that I think it’s better for health overall. And like you said, it was also with the bouncing around it’s like you’re good lymph nodes, health, and everything starts to move around. And then sometimes I do some of really simple yoga moves or sun salutation, really basic. That takes literally 510 minutes. And you don’t think it’s I think about the parallel and the metaphor here is you don’t think it’s doing much like you’re just walking around stretching, but in the long run and I think it’s huge benefits. Just like putting setting aside that one to $200 a month from your paycheck to a time is like, this is never going to save me. But 20 years later, it’s significant.

Yeah. In fact, I was just with my daughter on Saturday and we were talking about her four hundred and one K, and she was telling me how thrilled she is and she’s turning 26 and she is contributing the max every month. And I was telling her how meaningful that was for me. I had my 401K, balloons and it’s just so satisfying. It’s so great to be able to be a young person and saving money because it’s not the norm. Most people have a lot of credit card debt. They live hand to mouth. Whatever you can do to save money as you get older, it’s hard to think about it when you’re young. You think, oh, I’m never going to be 65. You know, that’s so far away. Yeah, but it’s not.

Yes, that’s true. That’s true. I love talking about money and I encourage people who are listening to this to really learn more on their own. Get a partner to learn about this topic because it’s not always available to certain communities and it’s especially underprivileged communities. I think that’s a huge problem to say, go get that free credit card. Don’t pay it off. It is a huge problem in your when you’re trying to invest in something, you’re trying to buy a house, your credit score becomes a problem that I’m seeing some of my friends have to go through painfully. So get smarter about money.

Even in your twenties, there are a lot of good resources. It might actually be like a nice thing for you to share with your listeners. I’ll send there a couple of courses that I’ve become aware of that are over zoom. And actually I was just in a book by Gene Chatsky, who is she used to be the financial reporter for the Today Show. And she has a website called Her MONEY.COM. I often contribute to that so I’m in this new book that they have, and it’s called something how to Money. How to money. And it’s for people in their 20s learning how to manage their money and grow their wealth. And these are invaluable skills.

Fantastic. We’ll definitely include that as one of the resources. Yeah, so the next question, I think we can talk about these things forever. There’s so many questions that people ask. For instance, one related to feedback. And when I took the course online, you know, LMBA with CFO, and I remember that’s one of the most key takeaways is how to give and how to receive feedback. It’s something that we never really learned in school, and it becomes even more polarized and awkward at work. So I would love to hear some of your tips about giving and receiving feedback at work.

Yeah, that’s a great question. So, first of all, I think the natural response to taking feedback is to get defensive. It’s very hard to hear criticism, forgetting, putting to one side how it’s delivered, because that’s another issue and we can talk about that. But regardless of how it’s delivered. Just trying to get yourself to calmly sit with it and not respond in the moment. Really take it on. Consider it. Think about it. And then come back with a response a few days later. Maybe a week later. And just to show your manager that you’re paying attention. That you’re listening. And maybe with a bit of a plan for how you’re planning on addressing it and getting better. That’s on the receiving end. In terms of providing feedback, there’s always been this theory, which I think still holds up quite well, this notion of for every negative thing you say to somebody, give them three positive things first. And you can even sandwich those things. You can give them two positives, one negative, and then a positive afterward. And be generous, just maybe contextualize as much as possible. I think sometimes people are in a hurry.

They don’t contextualize things, but it’s all in. It should be viewed and it should be delivered as a gift, as, I care about you, I care about your career and I want you to get better. And here is some information and here are some things, some tips, things that I learned as I was going through my career as a young person that helped me to get to improve in this particular area. So that’s assuming you have a really good manager. And most people don’t, sadly.

Sadly. But that’s great advice. I think we really need a reminders, like, oh, I’m in a hurry. Let me just give you this one negative or area need to improve. And we come back later. We’ll tell you something positive like, no, you have to structure it. And you’re right. Don’t rush it if you feel worked up. You know, don’t make decisions when you’re angry, when until everything kind of simmers down a little. Bit and make better decisions and make better conversations.

Yeah, it’s really true. And frankly, we’ve been in an incredible job market for the last year. So managers are trying desperately to retain good people. So they should be really incentivized to do this right and to get some help on it. If it’s on the strength of theirs, the market probably, the job market probably will be slowing down sometime around the fall. So this is the time for managers to really focus on retention when companies.

Need to keep people fantastic advice. There’s a kind of a more controversial question topic. I don’t think it’s that controversial, but the idea I’m ready, I was like, I love yeah, a lot of people experience, I have experiences in the past and have received feedback related to you’re now working in a clearly toxic, very negative environment. And we are often given the advice to say, you know what, you got to do your part. This is very common, just stick to it, milk the cow, do what’s necessary and then protect yourself first. And then look for a new opportunity. And what do you think of that advice? And what would you do differently or say to 20 year old?

I think if the person is truly toxic, I hate to say this, but unfortunately going to HR is probably not going to help because they’re there for a reason. There is a mechanism in place that you will never know. You’ll never decipher what it is. That person, they can’t get rid of that person. They’re probably aware, but for whatever reason they can’t. So what to do? I do think trying to have calm conversations when things are, when that manager is not hot and angry and just explaining how it makes you feel and don’t attack that person, but just take it. Just say, you know, the way you spoke to me earlier, it made me feel small and I’m hoping that we can find a better way to communicate, but ultimately just got to get out of there. If you’ve got a toxic manager, you really do have to get out. And I really as I said earlier, the job market is very robust right now. It is going to slow down. Look now, this is a great time to look. And companies are paying higher salaries. They realize that inflation is a big issue for their employees.

But of course the flip side of that is inflation is very real and companies are going to be contracting. So look for a new job.

I love it. Sometimes we have to be really straightforward and I don’t know what it was 1015 years ago, I personally didn’t receive a lot of very straightforward advice. There’s so much of you’re in your early twenty s and you should think on your own, be independent, but you really don’t have a lot of enough data points or experience to make.

How do you know?

How do you know, so I really appreciate your directness and helping students really guide, especially if something seem maybe even obvious to you, like something wow, you’re really heading towards the wrong direction. This is hurting you. Let’s do something about it.

Yeah, I mean, I’m remembering I was actually probably in my thirty s. I was in a meeting. The company I was working for had been acquired pretty recently and we were working on a proposal with this representative from the other company and he used an antisemitic slur when talking about the work that we were doing together. Not directed at me, but it was about the proposal. And I was so shocked, I merely went to him. My boss was with me, but I didn’t have a good boss, nor was he Jewish. So I also felt like he didn’t hear it the way I did. And I went to one of the founders of the company, or the original company that I work for. He was he turned bright red. He was so angry. He went right to the chairman of the company that had bought us and they fired the guy immediately.


And I was so grateful. That was the absolute best possible outcome. There’s just no place for that.

Yeah, I mean, that I would say not a lucky outcome. This is something that we have to acknowledge and address and to bring to somebody’s attention because the hardest thing that I have ever lived through. And for me, unlike a lot of my peers or a lot of other immigrants, I know that they work in these jobs I have not taken on. And they really felt bullied and discriminated against and I had very little of that experience. But the one thing I did live through was where the very high up was we’re in a financial institution, people who are well educated, very well dressed. And at the beginning I was kind of in this denial like this can’t be happening in Boston, in metropolitan city. And it just became very obvious that this very blonde, very blue eyed, and she kind of fits the profile. But those are not the only cues you need to look for. But she was right because anybody could.

Come from anybody could come from anyone.

And in this case she was very senior and very powerful woman and a woman which was really hurtful. And there happened to be a Mexican woman, a Chinese woman on her own team. And there’s me from the consulting side. And I know that she was very pointed, she was very dismissive, very negative when these people, including myself, would speak up. So I would observe and Alison, it’s kind of my own detriment of like, okay, let me just experience once, twice, three times and until in the end she made me do something. Printing out all the design on paper. I said, we have a projector, this is really not good. She organized at a green center, I kid you not. And she said in front of me, who asked you to print out all these things? Why don’t you just throw it away? I was literally walking over and she said there was going to be it’s.

Like a mountain of paper that she had made you print out.

Print out. And then she said, there’s going to be 18 people show up at a design session. That in itself is a whole other problem. But three people showed up.


So I literally had 80% overage on printout. And that was the time that I brought up to my manager, my supervisor at the time, and then they immediately blame it on me and said, we’re going to put you on a I actually said, please put me on a different project. And I remember, Alison, I never cried in my career, ever. I waited until I left the building. I walked another street over and I literally started crying. It was so hard.

It was so terrible. I’m so sorry.

I didn’t know what to do. Frankly. I look back to the experience and I hear these advice don’t waste the pain. Don’t waste that experience. What could you have done differently? And the funny thing, you’ll not believe this. I remember going back a couple of weeks later. The Mexican woman bought me this chocolate, like little gourmet chocolate. She didn’t say anything. She said, you know, I just want to give this to you. You’ve done such a wonderful job as a client. And the Chinese woman took me out to lunch with my mom in Newton. And she was so kind. She was like I was 27 at the time. She was like, I really admire your leadership. From up close and afar. I’m like leadership.

I don’t think wow, I love that.

I know it was and they had.

To, of course, stay there and take the heat from that awful woman.


That was crazy.

So now meeting you, I realized I was in my twenty s. I always felt like I should have done something. What could I have done at the time? What can we advise to other young people, potentially people of color or the community at large? Like, what can we do in that case?

Yeah, it’s really it’s very tough to know. I mean, I think in your case, you were fortunate that you were a consultant. Right. So I think if you in the position of a consultant, you could actually complain about her and there would be no retribution. You probably wouldn’t work with them again, but presumably you have moved on at that point. So I think that you’re in a great position to do something. Having said that, you’re 27. You don’t know what to do and who do you talk to and why would they believe you? It’s so much about the MeToo movement and what women have had to put up with over the years from toxic. Men thinking that they have just full rights to everything they want, and it’s similar, but somehow some more painful. It’s just differently painful when it’s racist or anything. I mean, we are unfortunately in a situation right now in this country where racism and antisemitism is absolute height, and thanks to certain administrations which condone this behavior, and I think people feel they can wear their feelings on their sleeve and harass people who look different from them.

Yeah, it’s very true. And for anybody who’s listening, whether you have experienced this personally, if you know someone who has, I think, frankly, number one, something you brought up, Allison, is to, number one, listen and believe in them as opposed to doubting them of this can’t be happening, because it’s really hard.

It’s hard to believe when it’s happening. You’re like, Did I hear that right? You can’t quite process it because it just feels like it comes out of the blue.

Yes, exactly. And I know that we’re certainly not going to lean into politics, but I even had a conversation with someone who did vote for that administration. I don’t have a lot of friends who did. Out of the two to three people, someone was close and said, well, nobody’s going to no faith. What do you mean? Against Asian people? Asian women? That can’t be happening.

Oh, yeah, now that’s not happening at all.

I know. It’s like, now I have to prove it and I have to talk about it. And really, it’s really hard to imagine. I said, Maybe I believe you won’t do anything right, like, you are a good person at heart. But sometimes when people hear a certain message, you’re right, all of a sudden they feel so righteous for, oh, I’ve been wanting to do this, and now it’s an opportunity. Now anybody could like Adam would say, you can run down 90 west or 90 east with your pants off. Just because you can’t doesn’t mean you should. And somebody can vouch for that and say, that’s okay. Then some people, even if the small percentage frankly, that would be too much to say. That’s okay.

Yeah. I’ve had so many conversations lately with people I know who are Chinese American or Asian American, and they are constantly having people say things to them on the street, go back to China and things like crazy, like crazy things. And this is totally new. Never happened before. COVID yeah, but they always believed that. They just now feel that they gave them permission.

Yeah. And the frequency of that’s happening right now, it is something I think especially for coming back to careers, it’s difficult. I frankly now, as an older person who is matured versus, my goodness, in my twenties, if this is happening every day, I don’t know how I would feel about going to work, how I be treated or looked at differently, even if it’s not from the majority of the people. But you just never know how that’s going to land. So. Thank you, Alison. I really appreciate it. And then you for opening up to this very challenging topic. And I think there’s an adjacent one, which is there are a lot of people on Google right now.

I segue.

This is actually related about me. Finally, as a result of that event, I will say a conclusion and related note is that I immediately decided to pivot. I knew that I had to leave the company, and as someone, by the way, an immigrant, I’ll be very open. I can’t just leave a job and go to another one. I have to land the job, file the paperwork, wait for the immigration delay, and then make that switch. So that night, as I was crying coming home, didn’t want to waste the pain, started looking for jobs, got four offers in two weeks. I was ready to go. But right now, commonly on Google, knowing that the opportunities are out there more variety than ever before, people in their 20s are really worried about, can you change your careers in your 20s? Is that a good idea? Does it look bad on a resume?

Yeah, that’s such a great topic. So, a few things. First of all, you can absolutely change your career at any time, honestly. But there are certain things that you have to do. So first, it depends on what you mean by change your career without doing anything differently. You can change your function or you can change your sector. You cannot do both without going back to school. So if you’re on marketing and you work in consumer goods, you could pretty straightforwardly get another job in marketing, working for a tech company. If you were in finance and your specialty was real estate, you could take a job in finance that was working for a consumer goods company. So you can definitely change one or the other. If you plan on making a wholesale change and you really want to go from finance in the tech sector to you want to become a social worker or you want to work in marketing for real estate development firm, you should probably go back to school. And what school? It depends. I mean, you could get an MBA that would reset you because you learn a lot of new skills.

You then have a chance to practice them in your internship and in the middle of the two year program. If you do a two year program or say you want to become a web developer, you could do a boot camp, and you could then become a UX designer, for example, in the same sector, but in a different capacity. So there are lots of ways that you can make change, but you do have to be mindful of how much change and then the requisite things that you have to do in order to make those changes.

Those are great advice because some of the questions that came through are I’ve made up my mind and I probably need to a lot of people are asking I probably need to go back to school and it becomes a very nerve wracking due to the very high tuition rates and thinking about what’s the likelihood of me making the same amount of money. More money. Or even less money in some cases. How do you think people should weigh in going back to school versus trying to make more money or thinking through.

Clear headed whenever anyone wants to make change like that? I always recommend that you find people to talk to. So obviously this is very obvious, but if you’re applying to master’s programs of any kind, MBAs or other types of masters programs, really important to go to the info sessions, ask questions, find out what people have done with that degree, find out if there are people who are currently doing what you do and what they did afterward. Were they able to easily pivot to this other idea that you have? The other thing is you can, especially when you’re a young person, you should go on LinkedIn and look for people who have done those degree programs or those boot camps or taken courses. There are so many different ways you can slice it and then look and see what their trajectory was and reach out to them and ask if they would be willing to have a chat with you. You suddenly decide you want to do something that’s more like in sustainability and maybe you’ve been working in the beauty industry and you want something that has more of an environmental stamp on it. There are so many directions you can go with that.

You could go into corporate social responsibility. You could get a master’s in something more very specific in environmental science and then you could go work for an aggre tech company in marketing. I mean, honestly, there are so many different iterations of this. But the most important thing is that you have some idea of how you want to take your transferable skills and apply them elsewhere and then talk to as many people as you can who have already made this transition and just make sure that this is the right degree program because it’s expensive. Sometimes you can get financial aid. There are different ways you can pay for things, but generally it’s expensive just to go to school because you’re out of the market for that period of time. You have no income at that time, so you can consult on the side. There are lots of ways to slice it. And don’t forget, community colleges have a lot of programming for career changes, especially people who are more low income, who need to work while they’re in school. They are an incredible resource and during the Obama administration they put a lot of money into those programs and they are so helpful, especially to, you know, new arrivals to the united States first generation college students, people who are lower income and have a lot of financial pressure.

They are really, really helpful resources, so don’t neglect those.

I love it. And Alison, in case you have any resources or links you would like to share.

Yeah, sure.

Thank you. I’ll try to wrap up with two questions. One is that there are a lot of startups and there has been startups since I was in school and a lot of young kids were running towards them, running towards these opportunities, working with other young people ideas. And sometimes they don’t even startups don’t even require all these fancy degrees and all that years of experience. So what’s your take on whether somebody in their 20s should join a startup and what are some of the things they should look for when joining the right or good startup?

So I’m a big fan of going to work for a startup. You can get all kinds of experience that you wouldn’t necessarily get in a bigger company or in a more established company. You know, you can sort of do five things in a startup when you maybe just had one job in a more traditional company. So it depends on your financial situation, how much stability you require. The earlier the stage, the less stable the startup is. But that’s also where the opportunity can lie. Now we’ve just been in incredibly fertile grounds for startups and that is starting to contract. There was just so much money being thrown at startups in the last couple of years, which is interesting because it was during Kogan. So I would say for the best combination of security like stability and getting in fairly early series a startups, typically they have their leadership team in place. Sometimes there are a few hundred people at that point and they’ve raised money. Look for a track record that the founders have looked for, founders who have started other companies and sold them successfully. You want to really look for a good team and you can get so much information just on LinkedIn alone, just looking at people.

So I would say that and I would say that everyone honestly, in an ideal world, you should get a degree. Even I understand if you get an associate’s degree and then you want to work and then make money in order to afford the next two years to get your BA, but nothing replaces that education. And even if some startups will hire people who are in the middle of their education, that’s great, it’s great to get some experience, but I really recommend going back to school and making sure you complete your education. You’ll thank yourself in later years because you’ll always be penalized for not finishing your degree.

Yeah, true. Especially like you said, a bachelor’s degree. We’re not even talking about your ultraphd postdoc or anything like that. I think just a bachelor. Just the bachelors, exactly. Because on one hand, yes, we have all heard 14 year old coders for getting fancy jobs, but that is far and few between and just you can rely on that, really, to be recognized, to really secure a job. My last question, Alison, as we can keep you on. It’s so fun to do these things.

I have fun. I love it.

I absolutely love it. And the last question is related to all these opportunities to become content creators. When I say that, yes, generally that’s the umbrella. You can start your own business and of course you can sell products, design things. And these days a lot of people come to me like, how do I become a part time or full time content creator? Specifically blogging, podcasting, YouTubing and Instagram influencers the whole thing. And I see a lot of young people, with some of them without a lot of experience and a lot of preparation to kind of hop right in, expect for quick and fruitful returns. And it’s hard. But at the same time, what’s funny, for my generation, there were not as many people in their 20s doing this, as opposed to people in their thirty s and forty s who wrote books, who really speak and then publish their articles. Now more and more people in their 20s started to do this. So I think it’s a pretty broad question. We can probably spend the entire other hour recording all the Q and A’s, but what’s your take, Alison? How does someone more wisely approach this?

So I have a pretty strong reaction to that question. I don’t believe there are obviously always exceptions, but generally speaking, I don’t believe that people should immediately start their own company. Because what do you know? You don’t know anything. Like, go get some experience working for someone who you respect and who does a great job in the area, in that field, and then start your own thing. What’s the rush? Obviously, everyone looks, oh, Mark Zuckerberg started Facebook in his dorm room and he dropped out of Harvard. And there are like five people who have been incredibly successful doing that. Five. You don’t hear about so many others. And there’s something deeply unattractive to me about the very brash, arrogant, very young person who is telling everybody how amazing they are and starting their own thing. And it sounds very sexy, but.


Don’T really believe that you have enough to offer. I think it’s much more respected to go ahead and work hard for somebody else and learn a lot and then start your own. So that’s my sort of unadulterated view.

Yeah, for sure. I think that initial experience, whether it’s working for two years or five or ten years, you really learn. And plus, you build all these connections that could serve you later on with people you could hire, you could learn from for your own company. And that is tremendous. And for anybody who is thinking about like, you have this hunger you have this desire to create value for other people. Great. Whether you’re a plumber, young. There’s a lot of young plumbers. That’s a really good job. As I learned. A lot of money. You can produce videos where you can show people how to use how to set something up.

Totally. Can I just interrupt? You say I should have said that if you want to test your skills, do it on the side. Like what you’re saying, this idea of setting up a side business, doing a side hustle, I think that’s fantastic. And then you really prove to yourself and other people that you can do it. I agree with you.

Yeah, for sure. And part time is important. I do not believe that, especially finance is an important element for you. You’re not living in your parents’basement. You don’t have a ton of savings and just drop everything to start an instagram account. That is not the way to go. Even if a lot of courses you spend $300,000 on tells you that you can do it within 90 days. No, most things do not happen in 90 days, and you want to find something longer term. So please let us know if you have any questions. I’m sure you probably have plenty of questions based on this hour plus the previous hour of conversation. And we love to answer your questions for sure. And thank you. Allison. Has this been so fun?

It’s always fun. Faye, I really appreciate your time. It was so much fun talking to you, and I love it. I love your questions. They’re all near and dear to my heart, and I’m always happy to talk to anybody if they have further questions.

Absolutely. And Alison’s contact information is all in the description below as part of the podcast Show Notes. So ask away. And with that said, I’m going to take us offline and finish the recording. Okay.

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