Episode 22: Pivot from employee to entrepreneur with Jenny Blake

Welcome to The Career Clarity Show, where we help you find a lucrative, soulful, and joyful career path for you!

Been thinking about making the leap into entrepreneurship, but need a plan to manage the risks? There’s a tactic you can try that’s surprisingly successful for budding entrepreneurs who are currently employed — and, also, quite uncommon.

The reason this particular tactic is so underutilized makes complete sense: asking your employer about it is risky, and there’s a possibility they won’t go for it.

But, if you’re successful, you’ll create the most cushy off-ramp ever and be able to build your business with ease. Want to know what it is?

It’s asking for the opportunity to switch from being a full-time employee to become a contractor.

In her book Pivot, former Google employee and business strategist Jenny Blake talks about doing exactly this when she left Google. She negotiated the switch from employee to contractor, and Google was (for a while) her sole contract as she built up the business around her book and coaching practice. (And in fact, even today, years later, Google is still a client of hers!)

Jenny found a win-win: giving the company what they needed while getting exactly what she wanted.

Allowing employees to switch to contract makes sense for companies for a lot of reasons: top talent is expensive to replace (and can take a long time to find a suitable backfill for), it frees up a desk in the office for another employee, it decreases the overhead cost of continuing to work with you, and (depending on how you negotiate your contract) it could also save them money. It’s actually shocking how mutually beneficial it can be!

But before you even *think* about requesting to work as a remote contractor, there’s one thing that must be true: you have to be kicking ass at your job.

If you’re not exactly the star employee, you don’t know how your work is creating value for the organization, or you’re on a performance improvement plan, you probably don’t have the leverage to get what you want to ask for. If that’s the case, you’re better off looking for a new bridge job where you can prove your worth and *then* ask that employer for the opportunity to shift to contract.

However, if you’re crushing it at work right now, are ready to move to a contractor role, and feel confident you’ve got leverage, here are 3 ways to set yourself up to get to yes with your employer.

#1 Seed the conversation far in advance

The number one thing that kills your boss’ ability to give you what you want is if they feel surprised by your request. (Stunned to hear that? Don’t be.)

If you approach someone with a seemingly out-of-the-blue request, even the strongest advocate bosses will feel unsure and unprepared to talk about it — not because they don’t support you, but because they won’t get time to pre-think about questions or ideas (which is especially important for introvert bosses). If they feel unprepared to talk about your dissatisfaction, they could be annoyed at the interruption. Or, if they feel blindsided by your dissatisfaction, they could be hurt that you hadn’t brought issues up sooner. No matter what, they’ll feel bamboozled.

The biology of bamboozlement (even for a fairly benign request) works against you. The most recent neurobiological research says that the emotional fingerprint of “surprise” in the body is actually the exact same as fear. The distinction between the two is the same as the distinction between frustration and anger: it’s a social differentiation in degrees of intensity — not a true biological or neurological difference. So if you surprise your boss with a request, you’re putting them into immediate fight/flight/freeze mode, which isn’t their most resourceful or empathetic thinking state.

Instead, you want to seed the pieces of the conversation in advance. If your boss doesn’t know you’re unhappy, they have no incentive to find a mutually beneficial solution, so you need to have met with your boss to talk about feeling dissatisfied at least 3 times.

These don’t need to be a formal meetings, either. If a calendar requested affair feels too stuffy to broach this topic, a pop-in to the office or a catch-up over lunch totally counts. Even a chance encounter in the hallway where you express some dissatisfaction helps prime the pump for the bigger conversation down the road.

Most people think emotions don’t have a place in workplace conversations like these, but most people are wrong. If your boss doesn’t see how this affects you emotionally, they won’t understand the magnitude or severity of your unhappiness. If they don’t get how frustrated you are, they won’t take your request seriously.

Beyond having several meetings to explain just how unhappy you are, you’ll also need to plant the idea that you have a potential solution you’d like to propose (but the idea might be a bit complicated). If you prepare them with the expectation that you want to talk about something tricky and need their help (and you’re not just complaining), they’ll switch into partnering with you instead of dismissing your feelings as just another disgruntled employee venting.

(This, by the way, was the key flaw in the way I personally approached this back at my last corporate job. I ended up having to make the leap to being a full-time entrepreneur without being a contractor because I turned my boss into an accidental nemesis instead of a collaborator.)

#2 Show them why it’s beneficial to them for you to work this way

If this ask is important to you (and you care about getting a yes), then act like it and prepare your ass off. Putting together a proposal, complete with statistics and suggestions, is a great way to show the company you’re not just pushing your luck — and that you’re good at what you do.

Do your research into how companies benefit from freelance employees and offer up all the cold, hard data, as well as any anecdotes you can find. This should be 100% about why this is great for the company — because the reasons it’s great for you are implicitly understood. Mention the things we’ve already talked about: cost savings, being able to throttle back over time (and train your replacement), saving space and money. Talk about what you’d still be doing in this new role so they understand what they’d be getting if they say yes.

Then, you need to explain t how your performance will be improved by this arrangement. Talk about productivity, availability, and any data you have to back these things up. If you work from home at all now, you can log the hours worked and work products created/accomplished on those days and contrast that to your days in the office.

If you haven’t seen it already, go watch Susan Colantuono’s TEDx Talk about “commercial mindset” ASAP. She discusses why just being valuable isn’t enough and why you need to learn to talk about your accomplishments through the lens of measurable business ROI. The more you can tie this arrangement to the visible impact for the company, the better your proposal will start to sound. So instead of saying that you working from home will be better for team morale, you can talk about how it allows you privacy for sensitive company phone calls at all times which will entice clients to renew their contracts with your company, while also allowing you to do fully focused work away from water cooler distractions that could make you less efficient, take longer, or cost more money.

You’ll also want to outline the company-specific contingencies to make this an easy yes: who else has done this at your company (whether it was transitioning to fully remote or to a full- or part-time contractor role)? How can you learn from, and avoid, their mistakes? Are there ways this can be a benefit, like having you closer to a client’s office so you can go on-site with them more often for meetings? Outline it all.

#3 Don’t take the first no as a final no

If your boss says “no” to your request, know this: only amateur-hour negotiators let the conversation stop at the first “no” and give up.

A famous piece of advice for anybody entering a negotiation is: “Yes lives in the land of No.”

Your goal is to steer the conversation to a place where your boss has some kind of next step: talking to their boss, talking to HR, reviewing the proposal you outlined.

Then, you may need to do some internal, politically savvy PR — talking to other people about how unhappy you are, how you’ve been thinking about this contract opportunity, and what a win-win it could be. If your boss feels like they are the only one fighting for you and don’t have any air cover, they won’t be motivated to pursue this very far. So think about some of the people they might turn to for advice — peers, their boss, HR, or someone else–and go tell them your story.

HR, in particular, can be an amazing ally, if you let them support you. As a former HR employee, Jenn is the perfect example of this. Her deep gift is that she helps you see the bigger picture of how work fits into your life and helps you craft a peaceful, joyful life that you love, too. So if you want help talking through this kind of work arrangement — or your strategy to approach it with your boss — Jenn could be the perfect coach for you.

SHOW NOTES:

• Learn more about Jenny and her work here
• Download her FREE Free Up Founder Time online course from NewYearNewKickassYou.com here!
• Recommended book: Burnout: Unlocking the Stress Cycle
• Recommended author: Michael Bungay Stanier
• Recommended book: It’s Not Your Money by Tosha Silver
• Recommended book: Outrageous Openness by Tosha Silver
• Recommended exercise: Jenny’s Ideal Day Mad Lib
• Read the Roadmap to Career Fulfillment eBook!
• Take the assessment on your top pillar of fulfillment here!
• Click here to learn more about our different coaching programs and offerings.

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