Find the Confidence for your Second Act

How to Find the Confidence to Ditch your 9-5 and Launch your Second Act

Finding confidence to start your Second Act after many years in Corporate America can be challenging.  Walking away from that security is frightening and intimidating.  Maybe you’ve been thinking about launching your own business for a while now, but the term “entrepreneur” sounds like a free-spirited twenty-something who has few responsibilities and little to lose. I hear you, my friend! After spending ten, twenty, or more years working your way up the corporate ladder, it takes a lot of confidence and courage to walk away from the familiar and step forward into your Second Act.

Fear of the unknown can be debilitating, and leaving the career you’ve pursued for years is daunting:  Will you be successful?  Will your ideas hold up to the test of customers and clients?  Will you even be able to get customers and clients?

And that’s all right. Don’t let your doubts and fears stop you. If you feel your soul dying a little more each day as you drive to work and walk to your desk, you know it’s time to make a change. If just showing up to work is emotionally, physically, or mentally draining, then you need to move on.

Why Life as an Entrepreneur is for You

Perhaps you’ve been thinking about starting your own business.  Maybe you even have a side hustle that’s been your inspiration.  But, you’re just not sure you have what it takes to go out on your own.

When you go to work each day, do you find it difficult to pay attention to what you’re doing because you’d rather be somewhere else?  Does your heart tell you to walk away from the day-to-day routine and pursue something beautiful?

You’re a creative soul. You have a passion for people – for a specific service or art form – that your current job simply doesn’t meet. Your work doesn’t bring you joy or peace.  Maybe you’re even a little depressed.

If any of these thoughts resonate with you, you know that change is critical.  Launching your Second Act can be the answer:  it will excite you, challenge you, and feed your soul.

How to Find the Confidence to Step Out Into the Unknown

  1. Make a plan.

It’s almost impossible to end up where you want to go if you don’t have a plan! Are there certain projects at work that you want to finish before you leave? Clean them up so you can leave with a clear conscience.

Look ahead at what you will need to do to start your own business and begin to get those things lined up. You don’t need to wait until everything is ready, but knowing what steps to take before you quit your job will provide peace of mind.

Check out BIZ Basics.  We designed it so you will know exactly what to do — step-by-step — to start your Second Act!  No more worrying “what did I forget.”

  1. Focus on what you want.

Start small.  Visualize daily where you want to be in the future. Will you remodel that grungy spare room that only gets used for storage and turn it into a lovely, pleasant office space? Picture it in your mind.

If you’re a visual person, start a vision board and create a vision binder. Print out or clip from magazines pictures of your perfect space.

Would you rather sell your home and travel? In that case, create a picture of yourself at all the exciting places you plan to see. Add pages to your binder for each destination and start to make notes about what you will do there, and what you need to do to get there!

  1. Don’t question yourself too much

Weighing the endless implications of leaving your career and the consequences of starting your own business is exhausting. If you spend too much time questioning yourself as you’re planning this new adventure, you’ll become more and more drained.

If you’re not thriving where you are now, there’s no reason to stay.  Yes, it’s a steady paycheck. And, yes, there’s the stability of having health care and the money to pay your bills, and . . . and . . . and . . . .  But, if you’re not living with joy and anticipation, then remember Anna, Elsa and the movie Frozen and just  “let it go!”

Allow yourself to dream. No matter how stable things seem right now, you don’t know what tomorrow will bring. There’s no guarantee that your job will last forever anyway, so why not pursue something that feeds your passion?

  1. Find Support

You’ll need support as you begin this new journey. A lot of it!  And, ideally, your friends and family will be right there cheering you on.

Some people might not be very supportive right away. They know how long and hard you’ve worked to get where you are now, and they worry that you’re throwing it all away.  They’re concerned about you and your future, but don’t let them discourage you.  Instead, search out others who will be passionate for you. Surround yourself with people who believe in you.  They’ll bring encouragement and faith and be your loudest cheerleaders.

Walk into Your Future with Confidence

One definition of confidence is “firm trust.” When you step into your Second Act as an entrepreneur, you’re putting firm trust in yourself:

  • You know who you are.
  • You have an abundance of strength and skill.
  • You’re powerful and passionate and well-equipped to take on this new adventure.

Starting a Second Act is not for the faint of heart, but it IS for the savvy woman who knows what she wants. Gaining confidence comes from having an appreciation and understanding of your best qualities and abilities.  Allow yourself to know and thrive in these qualities.

You Can Do This!

Over the years, you’ve built up a store of knowledge and wisdom that’s unique to you – don’t be afraid to share that knowledge.  And, as you start this adventure, use your wisdom to help others on theirs.

You can do this. I believe in you, and I would love to hear your story. Comment below and let me know where you are on your journey!


  1. All of this resonates with me. I was feeling that way last year and decided to do something about it. January I launched my business Sister Spotters, that supports women on the entrepreneurship journey. Right now I’m setting up my revenue funnels so that I am prepared to take the leap in 2018. Thanks for sharing!

    • Cindy says:

      Hi Trasetta, I’m so glad this resonated with you. Sometimes it’s really difficult to hold on to the confidence we work so hard to build. Thanks for the comment, and please let me know if I can help in any way. You’ve got this!

  2. Marlynella says:

    I find myself 100% in your article. I created my business since June 2016. The name of my business is Señora VA, it is a virtual assistant business. I have some clients, but not to cover my paycheck. I want to quit my job so bad, but I’m also so afraid to do it. I kept rethinking, selfdoubting myself..

    • Cindy says:

      Hi Marlynella, I’m so glad this resonated with you. Unfortunately, sometimes starting a new business can be a very slow process. Hold on to your confidence. You can do this! Please let me know if I can help.

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