Career Advice: If You Fake It, You Will Probably Not Make It

Here's some straight up career advice. If you fake it, you probably won't make it.

There's been a huge trend towards joining startups and fast growing tech companies ever since Wall Street blew up between 2008-2010.

The top companies to work for no longer are dominated by the Goldmans, Mckinseys, and Bains of the world. The Googles, Facebooks, and thousands of startups you've never heard of are the employers of choice now.

Nowhere To Hide In A Big Organization

Fake Ice Cubes: Can you tell? - Career Advice: If You Fake It, You Will Probably Not Make It
Fake or real?

One of the biggest realizations I've had going from an enormous investment bank to consulting for various startups is that if you fake it, you probably won't make it for very long.

When you're at a huge organization, it's easy to hide behind bureaucracy, layers of middle management, and massive amounts of inefficiencies. If you stop coming into work for a month at a large organization, chances are high the business will continue as usual. The extreme example is an Indian government employee who called in sick for 24 years!

At a small company, you must know your stuff and produce. Small companies generally have tighter budgets, less people by some definition, and a time limit to expiration given many startups are loss-making. If a company burns $10 million a year and only has $12 million left in the bank, the pressure is on!

There's no room for holding meetings about meetings on what to do. There's no room for people telling others what to do without doing anything themselves. Everybody must pitch in to produce something valuable.

Now think about the dichotomy between small companies and large companies from an investor's point of view. Do you want to invest your money in ex-growth companies where people have a tendency to come in late, leave early, and do the bare minimum? I don't. The hustle, drive, and innovation is why I'm a big fan of investing in growth companies and private startups. The problem now is that the private equity market is richly valued.

A Better Career Strategy

Here's some more career advice. Joining a small company may be beneficial for new graduates because there is much less hand-holding. It's either do or die. But I'm going to argue that for most people, it's much better to join a reputable large organization where you can learn all the fundamentals and THEN go work for a smaller company, or start your own.

Five reasons why it's better to start big, then going small:

1) Small companies fail more often than large companies.

If your company fails within a couple years of you joining, you might become “damaged goods” simply due to association. “Oh, so you were working at that company who stupidly spent all their funding on ineffective promotions. I'm never hiring you!” This is despite the fact that you were working in the engineering department and didn't have anything to do with the wasteful spending.

2) Large companies are more prestigious than smaller companies.

If you spend several years working at Apple, P&G, McKinsey, the Federal Reserve, or KKR, you're going to forever have a prestigious stamp on your resume that will allow more doors to open.

If you start at a company nobody has heard of and you want to move on, you better have done great things to prove your worth because employers will instantly wonder why you are moving on if things are so good. Having a prestigious firm on your resume acts as a perpetual screen mechanism for one of the likely seven or so jobs you'll have in your lifetime.

3) Large companies have more infrastructure to train you.

One of the best things about starting off my career at a large institution was the training. I got to go to class to pass my Series 7 and 63 tests. I got to take courses in leadership, accounting, finance, and communication to develop my skills. My next employer paid for my MBA for three years at Berkeley.

Meanwhile, I was able to get foreign language training in Mandarin for a year as well, all paid for by my employer. When you're at a small company, all you'll get is perhaps some free food and drinks to keep you in the office longer. Many smaller companies don't even provide 401k matches or profit sharing.

4) Large companies allow you to network with more people.

The larger the company, the larger the networking opportunities and the larger the alumni base. It's a fact that people tend to take care of people who have more similarities than less. Do not underestimate the power of relationships in getting ahead.

There's a reason why plenty of children of celebrities get coveted movie parts even though they can't act. There's a reason why average students get into prestigious schools. There's a reason why mediocre workers in your organization go much farther than you, even though you might be harder working.

5) Large companies may compensate you better than smaller companies.

Google no longer is a fast-growing startup, but they retain people like prisoners in a medieval dungeon because of its enormous balance sheet and massive profitability. Unfortunately for so many people who want to leave Google, a lot of other employers don't even bother because there are too many cases of Google matching and increasing any outside offer.

Joining a startup will likely make you poorer than richer over the long run given the below market cash compensation and the iffy liquidity events. Richer companies have a larger capacity to pay.

Related: How One Startup Founder Screwed His Employees

Career Advice: Watch Out Going From Big To Small

You know what happens when you work for a large organization where there are systems in place to take care of your every need? You tend to take things for granted. For example, I used to have my assistant book my flights and hotels whenever I went on a business trip.

It's a nice perk for being an Executive Director (one up from VP) at a large investment bank. Oh how nice it was for someone to do my expenses too. I just have to suck it up now as a small business owner and independent contractor.

Another drawback of going from big to small is the belief that you contributed more to the company's success than you really did. It's easy to think you're the shiznits when you've worked for a large, prestigious company for many years. The reality is that you're a much smaller cog in the wheel.

Ego inflation is a great concern for smaller companies hiring people from larger companies. If you want to know what you're really made of, try and create a business from the ground up.

Stay humble and always focus on doing things together as a team if you're making the transition from big to small. If not, you'll not only look like a prima donna, your incompetence will become very apparent.

Competition Will Always Be Fierce

The competition for good jobs will always be extremely competitive. If you can develop your skills at a large organization that has a lot of structure, you'll be more equipped to succeed in a smaller organization where there's nowhere to hide. If you can't get into a large organization, then you've got to put in double time to learn all you can. When you don't know the answer, simply say you don't know, but you'll find out.

At some point, we will all experience a situation where we don't really know what we're doing and will have to fake it to get by. That's OK, so long as we finally figure out what to do. But trust me when I say that embellishing your skills to work for a smaller company may only get you in the door. Eventually, you will get the boot if you lack substance.

So many people I know failed miserably at smaller shops after they left a bulge bracket firm because they no longer had a big name to attract any clients. Institutional clients have to talk to Morgan Stanley because they have a lot of deal flow, but clients need not speak to bucket shops. Once these job hoppers went down to the tier 3 realm, they could never return as their resumes were tainted.

Be careful what you wish for when taking a job that is tied to production. If you don't bring in the revenue, you will probably get fired. If you don't fill the top of the funnel faster than your predecessor, your days are numbered. If you're able to achieve great results, then you will get rewarded commensurately. There's something to be said about taking on a sleepy job that doesn't have pressure. You can fake it so much easier at a larger company. But where's the fun in that?

Don't Quit, Get Laid Off

My final career advice is: don't quit your job, get laid off and negotiate a severance package instead. Negotiating a severance enabled me to receive six years worth of living expenses from a company I dedicated 11 years of my life to. If I had quit, I wouldn't get any severance, deferred compensation, medical benefits, job assistance training or unemployment benefits and neither will you.

I believe so strongly in the message of never quitting that I spent a couple years writing this 200-page book entitled, “How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.” I'm absolutely certain this book will help you recognize your rights as an employee and break free from the corporate grind to do something you truly want to do.

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43 thoughts on “Career Advice: If You Fake It, You Will Probably Not Make It”

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  4. Brian @ Debtless in Texas

    Spot on, I started in the marketing world at a small company and the pay/hours were terrible. Making moves to larger and more prestigious companies allows for the ability to move back to smaller companies in a much higher role.

    The worst kinds of ‘startups’ are those that are large enough and pushing to go public, they pinch every penny and work you to death without the compensation. True steeping stones to a better job.

  5. Why would anyone want to work at a startup with huge growth potential and make valuable contributions and gain tons of experiences when they can work at a huge company and deliver TPS reports every week for the next 20 years?

    1. Many people probably would like to, but they’ve got to produce or else they will not last long. The amount of turnover in small companies and startups rival the turnover during cyclical downturns in the ultra competitive finance industry.

      Sure, you might make it big in a small company. But if you leave/get fired before your Cliff, that’s a big loss.

  6. That is hilarious about that Indian government employee! A lot of people dream of startup life without realizing how tough and competitive it really is. I’ve done both startup and large corporate work in my career and they certainly are vastly different. I most prefer the flexibility of freelancing, but I do miss the many benefits and perks from my corporate days.

  7. Gen Y Finance Guy

    I don’t know if I agree. I have always believed in the “fake it til you make it” philosophy. But like Mike mentioned above, you need to be a semi-intelligent person and I would add resourceful and have a willingness to hustle.

    But I think you and I may be comparing apples to oranges. Because I always intend on delivering, but there have been plenty of times in my career over the last 7 years, where I committed to projects that I had no idea how I would complete them.

    All I knew is that I had an opportunity to impress the big guys if I made it work. And with the internet everything is “figuroutable” to steal a line from Marie Forleo.

    Its kind of the whole ready, fire, aim philosophy.

    Of course their is risk, but that is half the fun. You know what they say…without risk their is no reward.


  8. Are these all your original thoughts Sam? Cause if so never stop writing…great stuff! This is essentially the exact blueprint of my career. Three years at huge company, great experience & opportunity right out of school…then 17 years at a small company. There is very little room for the non-A-Players at a small company, where as it is super easy to hide in a big one. Owning and operating a small company has proven a little bit of a curse though…now I look at most things from an efficiency perspective, both systemically and financially. I see how other companies run themselves and shake my head at how much money they leave on the table, the reality is though there just aren’t that many people who really get business and how to make money. Mediocrity just kills me & I suppose that was why it is a good time for me to have taken a break!

    1. Ha! Glad you enjoyed the post. Yes, these are my original thoughts. I’ve witnessed a lot of turnover at smaller companies over the past year and a half. It’s good to write in the moment, as that’s when writing becomes the most powerful.

  9. Some of the best paid roles are in sales and marketing. You eat what you kill. But these roles are also the highest turnover roles without a doubt.

    One has to be extra sure about their abilities in sales and marketing. Lots of people at Uber, for example probably think they are great. But the reality is, sales and marketing is easy when the product is great.

    Great products sell itself!

  10. Its odd, I never faked it at Walmart, routinely doing the work of 9+ departments. I focused on hard work, learning new skills/ policy that’d help in the next step and developing good working relationships with co-workers / bosses. If I had just spent my time faking it in a single department instead of busting my butt I most likeley would not have been terminated.

      1. Yes that is exactly it. I have no idea how to do that so I compensated by working harder and by becoming the only person in the store who could run some of the new technology. Its weird I would never have betrayed the company because I am 100% LLL (life long loyal) but now just because a customer steals $20 I am blamed and let go. I don’t understand this politics thing at all, I’ve made them way more then I ever cost them regardless of how they feel about me.

  11. Great post! I spent the first five years of my career at a big name firm for prestige and “training”. Since switching to a still large company, but with a different role, I can now say that I learned more in 1 year here than at the other 5 years combined with a big firm. On the other hand, I never would have gotten this job had I not got the “training” and prestige of my last firm. I think prestige matters – people trust you more and that is important. The next step is to go out on my own, but not until I’ve gotten everything I can out of this role. :)

  12. Reminds me of that movie “Catch Me if You Can”! I love the idea of being so smart, creative and not giving a crap, that you actually “fake it” just because you can.

    In all the jobs I had, especially when I went into completely new fields, like PR, music, tennis, and restaurant owner, I was always “faking it” to some extent, especially when I could feel that my clients or students really needed that reassurance of me being or acting like a “professional.” Why are we all so scared of the possibility of a little incompetence, especially if it’s not a life threatening situation? Let your employees breathe a little for crying out loud. Let them make a mistake or two and figure it out on their own. For this to happen, they have to be faking it. Why are we so obsessed with degrees, certificates and “years of experience” when it actually doesn’t matter that much. Who’s really good or an “expert” at anything anyway? Even the people at the top of their game are always still learning, improvising, figuring it out. . in other words, faking it!

      1. YoungBankerAndEntrepreneur

        Most of Sam’s post are way out of my league so I don’t read them but this one was a great post.

        Marco when I hear pathetic comments like that a small part of me smiles. Then I have a sigh of relief.

        People like you are the reason why employing individuals is tough. And also the reason why in the long haul – individuals who are obsessed with results – selling a great product (with a competent team), winning clients will win.

        If everyone was like Sam, my life would be much much tougher. You are exactly what he is describing in the article — an average person who thinks its okay to be average. “It’s okay to be wing it. Let’s all sing together and wear our corporate logos, and drink away the revenue of the firm in our business trip expenditures.. everyone at the top wings it don’t they after all? My manager doesn’t know what he’s doing even though he got an Engineering degree from MIT and has three successful start ups I don’t know about”

        LOL. Ill enjoy working my ass off over the next decade. Don’t complain when people like me have 10-15x your income “Pretending”.

        Good luck.

  13. Its so frustrating when your boss is the one faking it. Everyone can see that he is incompetent, lazy and milking the clock but he is a smooth talker and the Manager loves him and seems to think he is good for something. Its a little discouraging knowing he makes double what I do and does nothing of value. Often, I have to correct things he does wrong. Nonetheless, I still believe that by doing a good job at my work and being dedicated I will get ahead… Slowly..

    1. Unfortunately, just doing a good job is NOT enough to get ahead. You must sell yourself internally and build those political connections.

      Like you said, your boss is faking it. S/he isn’t doing work, but simply telling other people what to do in order to get the credit. That is work, but it’s not respected by the underlings.

      Politics is huge in a big corporation. It can be huge in a small corporation, but performance trumps all in a small corp.

  14. This is job/industry dependent. As an engineer, go small. My first job was with a 4 person company where I built a prototype within the first year that BMW threw in the trunk of one of their vehicles and test drove around the Alps. At a small company, you really get your hands on the technology and become an expert fast.

    I’ve since moved to a huge automaker. Great pay, fancy title… but I’m barely allowed to touch the tech. All R&D is done at HQ and is held very tightly by a small team. Most of my coworkers are barely competent because they’ve never ‘owned’ a system and can sort of hide it. At least I had the startup experience… I would be sort of screwed like most of them if my first job was at a giant company.

    1. Good point. Your situation to be able to CREATE from the get go sounds much more rewarding.

      But, are you or your coworkers really screwed with “great pay, fancy title” and the ability to kick back? That’s the dream for many!

      And if you are screwed, why not leave back to a small firm again where you can make a bigger difference?

      1. Being able to kick back may be the dream for many, but as you say… where’s the fun in that?

        I think about moving to an influential role at a small company all the time, but golden handcuffs are holding me back since I will be hard pressed to keep my salary level. The age old money v. job satisfaction.

        The best of both worlds is to start a side project while at a non-demanding day job. I probably won’t hustle that hard, but the current plan is to reach FI in ~3 years and then take the most interesting work regardless of pay. That’s what FI can do for me.

  15. I’ve faked it 3 times in my career… once when moving from a specialist role to a line role (Managing Director of an Operation with 600 people). This was a slow moving role since it took 6 months to replace the incumbent and I basically had my hands tied during that time. 2nd role was CEO of a 1100 person company- using my earlier job I knew enough to run an operation but had to fake all the cash flow & P&L / Balance sheet knowledge until it became correct. 3rd time was my most recent change- moving into a top Sales & Business Development role at a very prestigious international hospital. Totally new environment and culture, and have to use all my skills to keep my head above water.

    Basically fake it till you make it works if you have enough raw intelligence and are willing to work hard and with other talent to get to the point where you can create results fast. A bit of luck on the side when you start doesn’t hurt as well. It’s painful, but the only way to go.


      1. CEO of a $50M company to head of Marketing, Sales & Biz Dev of a $450M USD company… the progression makes sense to me. Plus it’s in a better industry (steady growth vs cyclical business).


  16. Wall StreetPlayboys

    Solid post as usual.

    You really want to get the *training* from a large firm then once you feel competent you want to be able to leverage your skills.

    Sometimes it is the same firm, other times it is jumping ship.

    Just remember. F*** prestige, get money.

    How do you get money? You get money by going UP the responsibility chain.

    Once you’re up the responsibility chain to revenue generation… It’s a whole different life full of stress, performance and effort.

    Finally, as Sam says… Don’t confuse talent for prestige. Just because you moved up at a large bank… You need to know if your sales are due to branding (the company) or you… Your contacts.

    you will never really “know” the difference. But. A good way to test yourself is look at your contacts.

    What percent were *handed down to you* and what percent were *created* by yourself.

    If you were able to create a lot of new relationships without the backing of a brand… You’re likely very good at what you do.

    Even then… Make sure you are CERTAIN, because the grass is always greener on the other side.

    1. Your contacts, relationships, clients…. that’s your true worth in a front office job. Bringing them over with you is when you move is the huge challenge. Hard to break inertia and a comfortable situation.

      Get the money, F the prestige… I like it. The prestige wears off in about a year.

  17. Really solid and true advice. However, having spent several years at one of the largest companies in the world, I can certainly see how some people receive very “pigeon-holed” training even in professional roles. Smaller companies may afford more varied exposure. But, your right that there is nowhere to hide in small companies and plenty in large companies.

    I saw one guy who literally never did a single thing in five years at a large company. Literally, not one thing, I am not exaggerating. He was the first guy in the office everyday and never had anything to work on.

    1. Once pigeon holed, one has to make the decision to get the hell out, or be satisfied with the situation.

      Well done by the guy who could get away with not doing anything for 5 years at a large company! Like making free money and benefits.

      It would be nice for a while, but I’d get too restless. But maybe those are the environments you want to have so you can work on your side hustle without risk.

  18. Great advice. When I joined my company it was considered as a medium size company. It was certainly not a start-up like many companies that my friends worked at. I enjoyed working at my company as there are so many things I can learn and a lot of people to help me along the way. Now the company has grown to about three times the size and it’s really neat to see the benefits of working in a big company. Faking it is never a good thing. The way I see it, faking it is like wasting your time. We all have a finite amount of time, why waste your time when you can use your time to learn things?

    1. Faking it is a symptom of fear, and a “oh shit, what have I gotten myself into” situation. I’ve noticed this happen a lot after new employees join a firm. It’s understandable b/c you have to sell yourself to get in.

      There are also extremely peculiar situations when you ask the new employee to demonstrate competence or examples of good work, and they will simply deny your request.

      A medium sized company sounds like the best of both worlds actually!

  19. I’m hitting the 10 year milestone next week (when my Long Service Leave kicks in!), working for one of the biggest professional services firms in the world. I’ve been mulling over a potential move to a small firm for a couple of years now, but have struggled to get past all the great things I’d be giving up (including a reasonable level of autonomy now that I’ve built up some valuable goodwill). I’ve always felt working at a smaller firm would be more ‘meaningful’, but it definitely doesn’t sound like the easiest move to make, especially when you have a nice, well-paid job with plenty of perks.

    I guess if I did move I’d probably feel like I’d need to fake it to some extent, as my experience has become very niche after 10 years doing the same thing (other than great leadership and management skills of course which hopefully have some relevance!)

    1. 10 years is a great milestone. Are you sure you don’t want to engineer your layoff and do something else? You’d be a perfect candidate, seriously!

      How much does the coziness of it all keep you with your firm? And tell us about this Long Service Leave. Is that like a nice paid sabbatical?

      1. I’d seriously love to engineer my layoff and try something else, and have been mulling over this for the last year or two, but I struggle to see how I can make that really work at a firm like ours – especially when right now they really need me!

        The coziness is definitely what keeps me here. I like the people, I can do the work well (sometimes very easily), I have some good flexibility and autonomy (sometimes), and of course all the perks of working with a huge professional services firm. I’ve almost left a few times now, but that coziness has definitely kept me there.

        Long Service Leave is pretty much a paid sabbatical – about 9 weeks worth at the 10 year mark. Apparently it dates back to the 1860’s where civil servants were given some extended leave to go home to Britain after 10 years service in the colonies. But if I left my firm I’d get it paid out. I’m tossing up the pros and cons on this and actually writing a post about it tomorrow.

        1. Jason,

          If you do not know of any resources, I have failed in my marketing efforts for my book, How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye. I have a chapter that discusses EXACTLY your situation, about how high performers in high demand can figure out a way to negotiate a severance.

          I actually just finished consulting with a guy who is literally going to walk away with over $500,000 in severance. He read my book, and took me up for a couple hours of live consulting. He make a lot of money in the first place as a MD at a large firm fyi.

          You have more power than you know. Employees need to know their rights. Tell you what. I’ll send you my book for free. But if you successfully engineer your layoff, send me over 10% of your severance. It will be one fine day!



          1. You have certainly not failed in your marketing efforts, and I am well aware of the book. I read all the related articles months ago deciding whether it was something that could work for me, and wasn’t convinced – possibly because it seemed more US focused particularly on healthcare benefits (which is not covered by employers here in Oz), but also just couldn’t envisage any scenario where my firm would want to let me go (perhaps I think I’m more valuable than I really am??) or that I’d even want to be ‘let go’.

            But I will gladly take you up on your offer Sam! It will certainly be a good option to consider in the mix at the moment, even if it seems a relatively low probability at the moment.

          2. Sam,

            Do you think a federal employee looking to leave the federal service would benefit from your book or does this only work for commercial business?

  20. Now 8 years into my career, I can strongly advocate this advice.

    I started my career in the commercial banking arena in a prestigious training program with a large (regional) bank. In my area of the country (Oklahoma), this is the path to take in commercial banking. I spent 3 years with this employer before jumping to a smaller (but very successful and prestigious) shop for another 3 years. I gained a small piece of ownership in this smaller shop and following a sale of the company to a very large bank in mid 2013, I jumped ship completely, leaving banking behind.

    I left to purchase a small struggling manufacturing company with a customer of mine from the bank where I last worked. He is retired, with ownership of several similar companies. Overnight I went from a VP at a bank to essentially the CEO of a small manufacturing company.

    To me, it is very freeing to have complete control. I know that I have the power to make the needed decisions to move the company in the direction that I want. Never again do I have to deal with the massive amounts of red tape in the corporate world. It is also very motivating to know that I am ultimately responsible for the success or failure of the company. So far so good with 48% revenue growth and a return to profitability in 2014, and a further 30% revenue growth in 2015 thus far.

    That being said, at 30 years old, I never would have been prepared to take on this role without the 6-7 years I spent at large employers surrounded by very high quality peers.

    For me, it truly was the way to go.

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