Since selling Burner Rocket, I’ve been working on finding the Next Great Move. This could include starting another company, joining another early-stage startup, or go somewhere where I can make good money – save and pursue my own company later with seed funds. However, now, I’ll need to consider a big next phase in my life – marriage.

My last post was supposed to go out on Wednesday per usual, but instead, was published on Saturday – three days later. Why? Because I was proposing to my then-girlfriend on Wednesday up in New Hampshire in the snow. (!!!) Yup! I’m going to have to edit my timeline soon.

In any case, I’m looking at three primary categories for what I do next:

  • Start another company. Pros: this is what I want to do. It’s what makes me the most excited. Cons: I do not have any clear interest in any one idea. Also, the SaaS market is highly saturated in marketing and sales, where I’ve spent my last two years. There is no clear wages here. (Danger given my upcoming nuptials and next-life-phase pieces like kids and new home.)
  • Join an early-stage company. Pros: continue to down the entrepreneurial path with some exit potential. Able to be a part of an early leadership crew to grow a company. Build something great from nothing/ little. If funded, can mitigate wage concerns. Cons: I would not be the entrepreneur, only entrepreneurial. How much of wage concerns can be mitigated? Will there be an ownership stake that enables some financial freedom upon a potential exit? Product-market fit may not be achieved and depending on leadership, leading the company to this point can take a long time… or never.
  • Join an organization that pays extremely well with learning upside. Pros: Can build up a cash stash to seed a future-startup. Will have less of the emotional roller coaster and be more even in stress-levels, likely. Can learn and network with vast resources and backing. Cons: Less entrepreneurial, if at all. Could be tied to golden handcuffs and never return to startups.

The point is to pursue one of these options early into 2019. Till then, I’ll continue filling my time with some consulting work to keep my mind sharp while learning and networking.

If you were taking a dive into another phase of your life, how are you evaluating your options? Why would you lean one way more than the other? What risks are you taking on?

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.