How To Bootstrap Your Career

The Aha! team is people-first, high-achieving, and purpose-driven. | Photo by Aha!

October 18, 2022

How To Bootstrap Your Career

by Brian de Haaff

I called it tech's "summer of pain." And now, to borrow from a much greater writer than myself, it seems like many folks are moving into the "winter of our discontent." People are searching for work or starting new jobs post-layoff. Others are feeling uncertain about what is to come. But rather than wallow, I think it is a good time to ponder what will help you stay grounded in the new year.

Our careers are much more than one job, one opportunity — gained or lost. How you approach your work is what carries you through.

Everyone deserves to find meaningful work. And many of us do. But too often it is the negative or splashy superficial news that attracts attention. That is one reason that I have written so much about bootstrapping this year — to show a different path is possible. Most of those blog posts were about lessons learned as a company founder. But I am aware that not everyone wants to or will be a founder.

This is why when Aha! launched the Bootstrap Movement earlier this year, we stressed that it is for everyone. Company founders, would-be entrepreneurs, and anyone who wants to work more effectively — the principles extend beyond how a business is funded. Rather it is a mindset. Bootstrappers set their own growth trajectory and work iteratively to achieve your goals.

If you embrace bootstrapping as a philosophy, that means it can be applied against many different efforts — including your day-to-day work.

Daily demands can bog you down. You may be pulled in so many directions that you feel scattered. And unfortunately, too many of us experience a toxic workplace at some point in our careers — no direction, big egos, and deep uncertainty. Amid this chaos, anyone would struggle to carve out time for focus on career goals. You begin to lose sight of your true aim.

You need a compass that will direct you towards what matters most. A bootstrap mindset can help. Here are five tangible ways you can apply the principles to growing your career:

Know your purpose

Words have power. Ask yourself — what do you want to achieve? Distill your answer to write a career sentence. Begin with a list of career goals and whittle down to the essence of what drives you. Your career sentence may be specific ("I solve business problems with technology") or more broad ("I bridge innovation and implementation"). Your career sentence may also be broad and aspirational. What matters is that you now have a north star. Reflect on it often. Say it out loud. Knowing your purpose leads to embodying it.

Mind the waste

Work waste is pernicious. Aimless meetings and pointless projects. It can be disguised as a quick win, with no lasting impact. It might be lurking in distracting drama. Or reckless spending, like the lavish lunch expensed to the company. Be the critical thinker and lean operator on your team. If you sense inefficiency, speak up. Would a different tool or process improve productivity? Can you do more with less? The ability to use resources wisely is essential for sustainable growth.

Be accountable

Actions have consequences. Doing what you say you will builds trust and encourages others to mirror your behavior. But accountability also means owning the unpleasant things. When mistakes happen or things do not go as planned, reflect on how to improve. There is no shame in learning. So ask for critical feedback from those around you. Listen closely and apply it continuously. This may be painful at times, but you will more deeply understand where you can further develop.

Take a long-range view

Growth takes time. Most career milestones are a moment in time — but millions of other moments precede it. Your daily work may not always directly support your career sentence but you can look for ways to live it. Look for opportunities to practice skills that will help you realize your goals. If leadership is your career aspiration, volunteer to lead a project or work on public speaking. Make the connection visible. Document these incremental gains in a journal or email to yourself to keep in a career folder. Revisit periodically to see your progress and be inspired for the journey ahead.

Put people first

Achievement propagates. Many folks will offer support to you along the way. Your success becomes an extension of their success. We can always help others no matter our role or position. So be generous with your knowledge and time. It is a privilege to do so and the reward is that it makes us better in return. Remember that we are all on this journey together.

Lasting career growth is purposeful, incremental, sometimes quiet — the right frame of mind can sustain you over time.

Leading the team at Aha! I have the privilege of supporting and witnessing others reach career milestones. And I know from experience that the achievements that bring the most meaning are the ones you worked for on your own. Being self-reliant, purpose-driven, and dedicated to creating real value will ensure that your path — however it may twist or turn — is lasting.

Interested in joining a bootstrapped company? Let's grow together.

Brian de Haaff

Brian de Haaff

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product development software — and the author of the bestseller Lovability and The Startup Adventure newsletter. Brian writes and speaks about product and company growth and the journey of pursuing a meaningful life.

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