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Before Making Moves Based On Today’s Bad, Chart How All The Dots Align to A Path

Tip: if you want to change jobs, roles, careers, think about what you want in the grander picture (“vision”), and why your current situation is not fulfilling that vision. Don’t focus only on why you’re not “happy”.
There are a lot of folks who are curious of new jobs, new companies, etc. They usually have the same reasons for wanting to leave. At least, for many of the folks I meet with who want to join a startup from a large company. The last several folks I’ve met with work at large enterprises. Each shared almost the same reasons for wanting to leave – they didn’t feel valued, and they wanted to work in a smaller company where their work mattered.
Except, companies (big or small, established or startup) are all different. They differ in their cultures. True many big companies come with much structure – multiple layers. Then again, so, too, could small companies have layers. Small companies can be directed by very strong founders who have sole discretion of direction and product.
Meanwhile, adding members to the Board due to a funding event will change the expectations and execution for a young company. Many of these are outside of the control of an employee.
There should be more focus on the position today. There’s a lot to learn in every position even the role someone may be in for the last 5 years. Too often, folks focus on the bad while missing the good – what is learned and what can be learned in a current situation. By focusing on the bad, folks go searching for new roles with a short-term view to “alleviate” the bad of a current position. This can lead to consistent change and unsatisfied work. Go beyond short-term objectives and take a look at the long-term view of goals and objectives.
Steve Jobs famously said in a Stanford commencement speech, “You can’t connect the dots looking forward; you can only connect them looking backwards. You have to trust that the dots will somehow connect in your future.” This also highlights an important point in that each decision leads to another decision which leads to many, many more. It gives freedom to take chances knowing that the dots connect but having that vision of where you want to go helps make the next dot fit closer to the trajectory you’re hoping for.
Before making that next jump, even before you ever feel “unhappy”, evaluate what your vision is for yourself. Then, evaluate how each position/ jump/ dot fits into the vision including where you stand today.
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Thinking About Joining a Startup? Don’t Overlook These Elements

I get a lot of folks asking me about joining a startup. Most have spent many years in the large corporate world. They start off by asking for recommendations of startups nearby and contacts I know. They think they know what they’re looking for. At least, they know what they are looking for right now. Rarely do folks take a hard look at what they want to achieve longer term. Then, how do they figure how a potential move now fits into the longer goal(s).
Before I go name-dropping startups, I always ask folks to think about the larger picture. There’s a lot of attention to startups because of the glitz and glamour media portrays. But there are big companies that can offer the right opportunities many startups can’t. It’s best to start with what your vision is – what drives you. Cue: Simon Sinek’s Start With Why.
Then, there are other elements oftentimes overlooked when considering startups…
  • The stage of the startup can influence the roles available. Generally, company growth can be split into a handful of stages — early, growth, and maturity. Early-stage companies are still figuring out product-market fit. They can change direction very quickly. Growth-stage companies are starting to optimize for scale. Here, roles are less “wear many hats” and more “this particular hat”. Mature companies go even finer with roles (sub-functions). As a prospect considers a role at a company, s/he needs to realize the agility that may be required. After all, most folks who ask about startups mention their interest to do many things.
  • How much funding has been raised — number of raises, how much, how many investors. Investors are pouring money into some companies to get in on potentially lucrative gains. Venture capitalists (VCs) are hoping to make up for that one big win in 20 companies invested to cover the fund and make significant returns. The more money, the more rounds of raise, the more investors mean the more pressure and expectations there are for timely returns. This pressure is put onto the executive team which will continue to flow down to every position of the company.
  • … about money raised, think about what the goal of the company and its shareholders may be. Is the goal to create a company that lasts and stays private (rare in the tech startup world)? Have a liquidation event (most common desired state, i.e. acquired by another firm)? Go public via an IPO? Whatever the strategy of the company is in funding, consider what the possible outcomes may be 2, 3, 5, or even 10 years down the road.
  • Again, what are you really after? Clayton Christensen, author of How Will You Measure Your Life, developed the Jobs-To-Be-Done Framework. He posits that everything we do or have has some purpose in life… a “job to be done”. In this way, what is the job the literal “job” should provide? Is it just money? Is it some fulfillment? Is it a place to meet friends? A startup is a company that provides goods or services to drive shareholder value. A corporation is no different – they’re all companies. How one startup executes its vision can be different from any other startup. This applies to large corporations as well. Thus, maybe what one is looking for is less about “startup” or size of company as much as it is purpose and vision or role.

Think about it. What’s your vision for yourself? How does your right-now fit into that vision? What does a startup offer that a large corporation may not? Or vice verse.

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How to Talk About a Part-Time Entrepreneurial Venture with Recruiters

I received a question recently from an entrepreneur about working part-time/ contract work as her startup continues to build momentum. She wasn’t sure how to talk about her company with potential head hunters. Head hunters advised her that employers could view her startup as a “conflict of interest”.
In the employers’ minds, the entrepreneur would be “taking advantage” of the company. The entrepreneur (read: “worker”) would be taking a higher rate, and leaving soon to work on her company.
My response is that there’s no “advantage” here. Instead, there’s mutually beneficial relationship. 
Some quick thoughts on this:
  • The employer is hiring a part-time/ contractor for flexibility and expertise. The employer does not have to pay for benefits, taxes (in most cases), and any severance packages. Meanwhile, the employer gets a skilled resource to address an exact business problem. It’s an beneficial arrangement for both parties.
  • A clear scope of work and deliverables ensures the entrepreneur is meeting expectations. It’s up to both parties if those expectations are exceeded (or not).
  • The entrepreneur should be upfront in her passions and what she wants to do. There is not a finite period of work at this point. It’s up to both parties to find a mutually beneficial arrangement. Again, the employer is looking for part-time/ contractor work anyways.
  • Big companies do, in fact, value entrepreneurial mindsets. These days, companies of all sizes realize the potential of more agile competitors. As such, companies are looking for capable, creative, and ambitious resources. These resources enable agility for companies.
  • Cultural fit is key. The right companies will realize fit with the entrepreneur, and vice versa. Some companies will leverage the entrepreneurial skills to bring a new product to market. Others may want the worker to augment a team and execute. In any case, it’s down to people on both sides to enable growth on both sides.

Entrepreneurial ventures can enable some of the best experience anyone can ever have. Through entrepreneurship, founders can learn all facets of the business with a real-world MBA. They’ll learn through the ups and downs of why corporations operate today. (Corporations exist and create structure to scale early success, after all.) For the entrepreneur, be confident and honest with what you’ve done. Be honest with what you want to achieve. Realize the right opportunity will enable both parties to benefit.

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