How to Navigate Change as an Entrepreneur with Jen Long


In the midst of a pandemic, as business as we know it is up-ended in every way, feeling disoriented and disheartened about your business makes sense. In that discomfort, it’s easy to slip you into a place of self-doubt and second-guessing all the decisions you’ve made that have landed you here.

Here. Sailing in turbulent waters. Maybe you’ve traveled waters this uncertain before; maybe it’s your first time. You may be energized by what’s happening; you may be more seasick than you thought possible.

So it’s a good time to remember: sailing uncharted seas is the essence of your job as an entrepreneur. It’s actually what drew you to be an entrepreneur in the first place; you’re naturally a steward of change, you’re naturally a navigator of the ever-changing elements.

Even in the calmest weather, building and growing a business is a wildly uncomfortable and messy process. Your business can act as a mirror, as a guide, and an extension of you. So it can be really hard to know what you should take personally about how it’s going and what you should take as a signal that it’s time to course-correct.

Indicators that it’s time to change how you’re operating can come in many guises. Sometimes the external world changes the game dramatically and the signs are unmistakable. Sometimes there are more subtle indicators that alert you to brewing situations that need attention.

One particularly tricky disguise for these indicators is growing frustration with what you perceive as a personal shortcoming. When indicators are experienced as indictments of yourself and your efforts, they tend to lock you out of your power, and stymie progress.

These indicators-masquerading-as-indictments can shapeshift into a lot of different “truths”. Here’s a shortlist of very common ones:

  • “I think it’s a self-worth issue.”
  • “I’m working really hard but I feel like I’m spinning my wheels.”
  • “I know I’m past my boundaries but I don’t want to just walk away.”
  • “I’m wondering why I got into this in the first place.”
  • “I’m really tired and I just don’t care anymore.”
  • “I have a million ideas but I can’t figure out which ones to do.”
  • “I was so excited about it, but then I got overwhelmed and stopped.”

Recognizing the belief or thought for what it really is – an invitation to do things differently – is step one towards getting unstuck. Step two requires taking action to figure out what to change, and how to change it.

There’s a truism in sailing: you can’t sail straight into the wind. You need to angle your sails to the wind in order to let the wind fill them and propel you forward. Here are three tried-and-true, simple and powerful, ways to help the winds of change fill your sails:

  1. Get some outside perspective. Reach out to at least a few people who have relevant experience doing what you’re trying to do. Let them give you the invaluable gift of seeing the bigger picture.
  2. Collaborate with your peers. Joining forces with people in similar situations gives you the exponential advantage of not having to figure each and everything out by yourself.
  3. Spend some time with your numbers. Learning how to interpret your numbers and mock-up future scenarios will make decision-making less daunting.

For a free introduction to understanding your numbers, join Jen Long during RA MA Business School: Pivots, Transitions, and Opportunities – a full-day event streaming LIVE all day on Friday, April 24th. Sign up here.

We’d love to hear from you – What are your techniques for knowing when and how to make changes in your business?



After 10+ years in the world of SF Bay Area start-ups, in product, business development, co-founder & advisor roles, Jen Long is now consulting & coaching early-stage entrepreneurs & small business owners.

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