A disclaimer: I want you to move to a startup. I’m hugely biased. I think entrepreneurship and working in a small business is a boon to the economy, it’s fulfilling professionally, and it’s a rewarding lifestyle.

It’s just not easy to understand, sometimes. There are a lot of misconceptions, and there’s plenty of uncertainty (even for serial entrepreneurs).

If you’re not properly informed or you have unreasonable expectations, you’re simply not going to be happy and effective in a startup role. That’s no good for you, or for the startup you join. I’m here to make the handshake a little easier.


Not a magic career pill

When friends ask me whether a particular startup they’ve found would be a good fit for them, my answer is the same for everyone:

“Uh, maybe? Depends.”

It’s a bit like being asked if I believe they could meet their soulmate at the bar tonight. What’s a good friend going to say other than “sure, why not?” with a shrug? Do you know what your ideal job / perfect soulmate is? Career movers need to understand what they want before deciding whether jumping from ‘big corporate’ into a startup role is a good idea for them.

I sense that some people believe that a startup role could be a magic problem-solving pill that’ll wash away their job dissatisfaction. Startups are supposed to be so different from the typical corporate gig—for all the reasons I’ll include below and many, many more — and they bring their own collection of risks and rewards. Are these the risks and rewards you want?

Startup environment & culture

Some of the differences you’ll notice in your first weeks at a startup role.

Things you likely won’t find (or miss) at a startup:

  • So many meetings—small businesses are often evaluated on how quickly they’re able to scale, and therefore value execution over consensus. You can’t grow when teams are tied up in the boardroom.
  • Coasters — those not-very-ambitious colleagues who are happy to complete their 40 hours but won’t stick a neck out. Startups can spot this persona quickly and won’t risk the slow ramp-up, the lack of impetus and the drag on team motivation. If they do sneak on board, they don’t last.
  • “Incoming” work — your team will rely on your own professional know-how to create a plan and execute. Your day-to-day work won’t be entirely delegated, it’ll be on you to conceptualize a strategy and make it real. That also means getting buy-in, setting goals and proving the concept.
  • Specialists — until a startup reaches a certain, sustainable size, employees tend to be flexible all-rounder performers getting shit done. Many entrepreneurs wear this like a badge of pride. One startup team I know calls it being “relentlessly resourceful” and I think that nails it.

Things that still exist at startups despite everything you may have heard:

  • Cliques — cliques are made of people and startups are made of people. There’s no guarantee that small company of 20 is made up of a wholesome, democratic family of friends. It’s equally likely to be composed of isolated groups who rarely collaborate, with a handful of uncomfortable outsiders who wonder what they got themselves into.
  • Job dissatisfaction — not every startup is saving the world or writing the code for the next social platform. Some startups are the third, fourth or hundredth attempt at revolutionizing a static opportunity. If you’re moving jobs for the warm fuzzy feeling of changing the world (and good on you), research the market and founders as well as the company.
  • Politics — in the same category as cliques, some people are just motivated to get ahead despite others and they work at startups, too.
  • Job insecurity — most people understand the inherent risk of joining a startup, solvency and funding and all. What some don’t expect is the same leaders’ unapologetic position on layoffs and saving face. Redundancies are a reality even at a small company, and can feel that much more personal when you work across the table from the CEO.

Things you may actually miss from a corporate job once you jump into a small company:

  • Seasoned leaders — many entrepreneurs are on their very first business. Don’t underestimate how important leadership is to direction, stability and success. The ideal startup founder has failed and succeeded enough times (both equally important, in my opinion) to have the wisdom to steer the team to an exit. You’ll feel the absence of leadership when you’re on a team running without enough experience, and when you can’t find a role model worthy of emulating.
  • Process — those restrictive, inflexible “workflows” that you followed at Big Company were there to get the job done on a budget. You’ll have to get your work done at a startup without that framework. It may sound appealing at first, but can you handle the pressure that comes with executing on-time, on budget and in a new environment if it’s a do-or-die project where you’re seen as the only expert?
  • Benefits and matching—some startups invest in their people and will lay the cash out for a great benefits plan, but not all. Some want to hit a milestone before paying into a benefits plan. I’ve never seen an RRSP match, a pension plan or a hefty bonus as a significant part of startup comp. Consider the entire package you’re giving up by moving away.

The very best aspects of startup life that I hope you find:

  • Sharing vision and success — when a group comes together to rally around a monumental company challenge, and then knocks it out of the park; I’ve never experienced a more spiritual reason to just party.
  • Authentic support — every company claims to have a team that gels and supports each other, but you’ll know it when you really have it. Genuine support is never being afraid to ask for help because you know there’s no judgement. When you recognize you’re in it together, you ignore the superficial stuff and can fully focus on the customer.
  • Learning everything — thanks to the many hats you’ll wear in your new get-shit-done role, one day you’ll wake up and realize just how much you can do now that you couldn’t before. You closed your first customer, hired an exceptional A-player, got a Twitter “Like” from your idol CEO in the valley, fixed the leaky sink, avoided disaster by inches, mourned a friend leaving the company, got funded, moved to a larger office, released a huge product update, released a patch for that update, fixed the new office’s leaky sink, landed an enterprise client, etc. It’ll blow your mind.

Will the culture be very different?

Startups need to attract talent without blowing all their cash on salaries. Especially during the dot-com era, many startups attracted talent with the promise of three key things; equity (combating risk and improving comp), team culture (supporting work-life-balance) and purpose (making an impact that’s felt by the team and its customers).

Startups are more popular today. Millennials, especially, consider working for startups and many forego a big paycheck in favor of finding purpose. Personally, I believe an effective culture is one that helps the team find work-life balance. If people are stressed out regularly, there’s a culture problem. If no-one ever stays late to tackle a critical problem, there’s a culture problem.

Will the work environment be super different?

Dress-code? Probably, yeah. I’ve never seen a startup allow a tie through the door unless the investors or customers are visiting. Dark jeans and a dressier shirt are the most formal attire I’d expect, though mid-sized companies may begin to demand better dress from their leadership as the team grows.

There will likely be fewer formal meetings. Startups are about execution and that doesn’t happen when many resources are tied up in the boardroom. Standup meetings are popular — Twitter-sized updates about tasks and challenges where everyone speaks round-robin style. Startups get a lot of their transparency and efficiency from short, open meetings like these. Every team is different, but meeting cadence is usually a big part of the culture and work style.

The team will be young. Strictly speaking in the aggregate, most startup teams are younger professionals between mid-twenties and thirties with a handful of people outside of that range. You might report to someone younger than you — it means nothing. They either joined early and therefore assumed more risk than you did, or they’re all-stars and it should be a riot being on their team.

Something I look for in evaluating a startup is founder experience — I seek out founders who’ve had a few wins and losses under their belts. I find they have more patience, tolerance for risk and a work style that reduces stress for the whole team. When the CEO is stressed, it shows. It’s totally acceptable to politely ask about the CEO’s experience in your job interview.

The office might be a cool, trendy loft or it might not. Most are accessible by transit and near the core to reach as much young talent as possible. There will probably not be free parking so consider ditching the car if you only own it for the commute. Plenty of startups are working in shared spaces like incubators, joint offices and communal workspaces. Very few startups can afford to (or ever want to) invest in cubicles or private walled offices.

Where I live, in Toronto, many startups have established themselves in the west side of the core, between Liberty Village and Spadina — and along Bloor; the rent is affordable and the commute is reasonable. Hooray for Toronto; there are plenty of historic office buildings in these areas and some of the offices I’ve visited are really sleek. I’d count on a decent workspace.

How’s the move to a startup going to affect my resume?

Millennials move. It’s a generational reality. I’ve made of a few hops myself, and, like most professionals I support these decisions with a strong story and rationale. If moving to a startup ‘feels’ like a bad move in your gut, ask yourself what the story sounds like. Why does it make you uncomfortable to tell it?

The more common worries and justifications:

  • “People may think I’m nuts for leaving a well-paying but boring job”
    Just as many people would call you crazy for staying, too. Life’s too short for an unfulfilling career.
  • “What if the startup fails?”
    The honest truth is you’ll be on the job hunt again. You will never be held directly accountable for a startup’s failure. Make sure to buffer emergency savings (at least two months’ rent and living expenses).
  • “Will it help my professional development?”
    I always say yes, of course. Startups offer a whole new perspective on how businesses grow. Even if your responsibilities were identical to your old job (they won’t be), it’s eye-opening to participate at the early stages of growth — and not in a business-as-usual environment.
  • “Will I build my network?”
    Yes. Though I always caution friends and colleagues who make moves into the startup space that it can feel like hitting the reset button. Make sure to put your network skills into overdrive for your first twelve months in the new job to create connections in this new environment.

How will my work change?

This totally depends on the company, the team, the leadership, and the stage of growth. There will certainly be a significant change in the nature of how work is delegated. Ben Horowitz wrote a smart piece about large-company executives being lost in small company roles, and how small company employees need to assign their own work. The CEO is too busy to delegate all day and likely needs your domain expertise, so a self-starter work style will take you a long way as a member of the team.

Is it true small companies move much faster than large ones?

Okay, kind of yes — but what does that mean and how does that impact your day-to-day or month-to-month work? It takes a few forms.

First, decisions are made by management over the course of a few days or maybe weeks, and then they’re put in motion. Most big decisions are decisions at all because they’re pressing, and need action. Often it means “stop doing things this way and start doing them this way instead, starting today.” Some people can’t handle that, so make sure you’re comfortable changing priorities semi-frequently and often drastically.

Projects and teams are typically smaller. Instead of a group of five or eight or whatever number of corporate stakeholders being “in” on a project, your projects are meant just for you and maybe one or two others. You can reach consensus faster but you’ll also have fewer resources.

The market changes quickly. These following events have happened to teams I’ve personally been on, and my career isn’t nearly as long as many other startup junkies who have probably seen some serious shit:

  • A competitor launched and posed a threat to big customer deals within weeks of our hearing about them.
  • Our coveted first-rank position on a Google search results page dropped nearly overnight, threatening leads and ultimately revenue.
  • A web vendor’s update brought down our product, locking out users.
  • A big customer went bankrupt. So, nearly, did we.

Do any of these problems sound like issues we could resolve cautiously and by committee at the monthly team alignment meeting? 
Startups plan, execute and hustle to survive.

It comes down to a very, very familiar thing

Are you going to be happy?

Only your gut and maybe your spouse and your mom can tell you that with any certainty.

Enjoy the ride and good luck!


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